[[folder: Sun On Yee]]
!!Wei Shen (Voiced by Creator/WillYunLee)

->'''Raymond:''' We're cops, there are rules.\\
'''Wei:''' You're a cop. I am an ''undercover'' cop. The rules are different!

Protagonist of ''Sleeping Dogs'', Wei Shen is a Chinese-American undercover police officer from the San Francisco Police Department tasked by the Hong Kong Police Force to infiltrate the Sun On Yee and bring it down from within. At the age of 10, he moved to San Francisco with his mother Margaret Shen and sister Mimi Shen in hopes to get the latter off her drug habit. Unfortunately, she couldn't kick the habit and overdosed; Margaret later committed suicide following Mimi's death. Despite the trouble haunting his family, Wei distinguished him quite a bit academically in his youth, passing High School with honors, and eventually enrolling in San Francisco Police Academy, where his intelligence, physical skill, and natural aptitude for police work, allowed him to pass with flying colors and he went on to become a highly regarded police officer. Throughout his career, Wei has showed a deep understanding of the triad structure operating in San Francisco, making him the perfect undercover operator, yet beneath his exterior lies a psychologically exhausted and stressed man who wants nothing but vengeance on the gangs that destroyed his family and life.

Catching the eye of Hong Kong Police Force Superintendant Thomas Pendrew, Wei is recruited for undercover operations in Hong Kong, returning back to the city where he was born.

* TheAce: An excellent martial artist, marksman, driver, hacker, singer, talker, and is highly intelligent and attractive.
* AmbiguousDisorder: While the game proper never gets into it, the police files on Wei make it pretty clear that contrary to his perfect social functioning he's pretty far gone into something. It's still unclear if it's a disorder or a really adaptable personality.
* AntiHero: UnscrupulousHero
* BadassDriver
* BadassInANiceSuit: Can be one if the player choose. [[spoiler:Definitely is one during the wedding, the funeral, and the final mission.]]
* BewareTheNiceOnes: He's actually a well balanced and caring individual during normal times. But you can't forget that anyone who has threatened his friends & family has never came back, alive.
* BecomingTheMask: Wei's psychological profile indicates that this is a potential danger due to how malleable his persona is, but it's also what makes him such a great mole. When he's with the triads he's a full-on gangster; when he's in police mode, he suddenly shifts gears mentally. Nevertheless, it's his main source of conflict with Raymond, particularly when Superintendent Pendrew's orders are for Jackie to be brought in.
* BullyHunter: According to his biography, Wei has been reprimanded 6 times for violence and/or fighting when he was in high school and he has zero criminal record and tested negative on all drug test. This means that he never joined any criminal gangs or was ever arrested for committing any crimes growing up in the US. He being reprimanded in high school yet still graduating with honor could stem from him either fighting bullies or possibly other gang members.
* ByronicHero: Wei at first appears like a generic cop AntiHero, with a heavy aversion to killing anyone except the target of his revenge: [[spoiler:Dogeyes, whom he plans to murder. Then after the warehouse gunfight, where he is forced to kill many people for no reason other than survival, the trauma of it wakes up Wei's dark side and he quickly becomes this. Attractive? Check. Brooding to the point of setting up titanium thick emotional walls? Check. Haunted by both a significant loss AND a past crime? Check. Passionate in his beliefs? Check. Heavy conflict with other's philosophies and especially with authority that results in (temporary) rejection/exile from the police force via Pendrew and social isolation from the surviving Triad members ? Check. His transition to Byronic Hero is exemplified as the takedowns he can use get more and more brutal as the game goes on, starting with simple (if harsh) knockouts when he is still just an upstanding AntiHero and eventually evolving into impaling people on Sword-fish heads or burning them to death as he is more and more convinced that underground UsefulNotes/HongKong (barring his branch of the [[UndyingLoyalty Sun On Yee]]) deserves to burn.]]
* ConflictingLoyalty: Raymond grows unsure about Wei's loyalty when [[spoiler: he achieves the rank of red pole]], fearing Wei will hesitate between keeping playing his act or fully embracing his role as a Triad. [[spoiler:The end of the game has him sticking with the cops despite Pendrew's backstabbing, if only because he ends up getting back at Pendrew in the end, but he tells Inspector Teng at the end that he's not sure what he'll do next]].
** Considering that [[spoiler:during Wei's captivity a henchman can be heard voicing his belief that the revelation of Wei being a rat is only an excuse to wipe out his faction]], it's entirely possible that the secret of Wei's undercover status died with [[spoiler:Big Smile Lee's faction]], while [[spoiler:[[TheDon Broken Nose Jiang]] and Pockmark Cheuk may not have told anyone else]].
** [[spoiler: Pockmark Cheuk asks what is to become of Wei Shen. Broken Nose Jiang orders to leave him be as Wei Shen was loyal to her in the end.]]
* CunningLinguist: Zig-zagged; Wei clearly knows Cantonese and uses that knowledge to his advantage multiple times but never speaks it himself in the game. This [[http://kotaku.com/what-sleeping-dogs-gets-so-right-about-being-an-asian-a-1644011008 article]] explains how not doing so keeps the audience from being alienated and emphasizes him as having been raised as an Asian-American.
* DarkAndTroubledPast: Life has never been kind for him. People that he cares about keep on dying on him. [[spoiler: [[FromBadToWorse And it could only get worse]] after coming back to Hong Kong due to undercover work. Luckily, [[EarnYourHappyEnding he manages to earn his own albeit, Bitter Sweet Ending]].]]
* {{Determinator}}: In the last two missions, [[spoiler: Wei gets sliced, drilled, hammered, shot and pistol whipped (and those are just the cut scenes), yet keeps on going to ensure that "Big Smile" Lee pays for Jackie's murder]].
* EveryoneLovesBlondes: He mentions to Peggy that he has a thing for blond women. His mother, who didn't like the idea of him going steady with a white girl, didn't approve.
* ExtremeMeleeRevenge: His epic beatdown on [[spoiler: Mr. Tong]]'s smug face. [[AssholeVictim Hard to argue it wasn't deserved though]].
* FantasyHelmetEnforcement: Wei always wears a helmet when riding a motorcycle, even when stopping to put it on is inconvenient. The exception is when he's already wearing headgear, like a hat.
* FieldPromotion: Within the triads, Wei becomes Winston Chu's lead enforcer after earning his trust. [[spoiler: When Winston is killed, Wei inherits ''de facto'' leadership of Winston's Water Street Boys gang, which is later formally confirmed with a promotion to Red Pole]].
* GeniusBruiser: He pretty much has to be this as a undercover cop given how this is almost a mandatory requirement for many police and government agencies. Also he graduated high school with honors despite being reprimanded 6 times for for violence and/or fighting. He briefly studied politics at San Francisco State University
* HeWhoFightsMonsters: Spends the game teetering on the edge of this. His suitability report says he has been suspected of ignoring the line between undercover work and enforcing the law in order to settle personal vendettas when he was in San Francisco and he is often threatened by Raymond of being taken out of the field because he's becoming too much like the people he's pursuing.
* HyperspaceArsenal: Averted; Wei can eventually carry a concealed handgun on his person, but heavier guns and melee weapons have to be either found in the environment[[note]]one of the ends of the Police upgrade tree (thus at earliest the fifth upgrade) is the Police Trunk Key, which lets Wei collect a Pump Action Shotgun from the trunk of any police cruiser[[/note]] or taken from disarmed/beaten/killed enemies and cannot be stored anywhere. Additionally, the amount of ammo Wei can carry for firearms never exceeds four magazines plus the currently-loaded magazine.
* InkSuitActor: Compare Wei's facial appearance to Will Yun Lee.
* ItsPersonal: [[spoiler:Jackie's murder]] causes Wei to throw away all restraint and he comes for [[spoiler:"Big Smile" Lee's]] head with no mercy for anyone who would dare oppose him.
* MadeOfIron: [[spoiler:Especially during the second to last mission. He's given small cuts with a scalpel, gets a drill through his legs, his toes hammered and punched around before [[UnstoppableRage he's had enough and tears the goons a new one]]]].
* MagicTool: Wei's battered police-issued smartphone can do things such as hacking security cameras, computers and safes, but can also trace a phone signal in mere seconds and calibrate a spy microphone. For greater absurdity, it can send pictures with a high enough resolution to be used as legal evidence in literally a few seconds.
* MaleGaze: Checks out Sandra's behind in the cutscene at the beginning of their date.
* TheMole: Not just against the Sun On Yee, but against the Tongs back in California.
** MoleInCharge: [[spoiler:After Winston's death, he takes his place and become a Red Pole]].
* OfficialCouple: with "Not-Ping," if ''Nightmare at North Point'' is of any indication.
* OneManArmy: By the end of the game, he would have wrapped up a kill count that can rival [[ThePunisher Frank Castle]].
* PayEvilUntoEvil: Practically standard operating procedure as far as Wei is concerned.
* RabidCop: A rare well-intentioned example. Though he is a dangerous man, he gets away with the kind of things that would get any other detective thrown in jail, but only because most of the people he reports to don't care how many mooks have to die to bring down Sun On Yee's top echelons (though one of the people assigned to work with him worries that his time as an undercover cop could bite them in the back if they let him get too close to those who hurt him in the past). In the ''Year of the Snake'' DLC, he's busted down to beat cop, because the superiors have finally had it with his exploits and excessive violence.
* RevengeBeforeReason: His dossier says he tends to be a loose cannon when left to his own devices, often trading his role as a law enforcer in order to get legitimate revenge while working undercover.
* SharpDressedMan: In a way, the game doesn't force the player to have Wei wear a suit but by the end game he'll wear a lot of them for quests. Also the games clothes all are somehow conveniently limited to colors aligning with Wei's winter complexion.
* SociopathicHero: He's fighting to bring down the Sun On Yee, but his methods involve being a willing agent of them. That's on top of how brutal some of his environmental takedowns can be.
* TheSouthpaw: It's not brought attention to but Wei holds his phone and most one handed objects in his left hand (guns are the logical exception, though he holds a pistol in his left hand on the cover). In fights he also always punches first with his left hand.
* TattooedCrook: Subtly played with; his left shoulder and upper arm bears a tattoo of Guan Yu, a Chinese deity who as a patron deity of brotherhood has been worshipped by both Hong Kong police ''and'' the triads.
* TechnicalPacifist: Early on, Jackie expresses alarm that Wei killed a guy, but Wei says, "Nah, he'll live. He'll have to eat through a straw for a while, though." Of course, later on he clearly has no problems killing his enemies.
* UnstoppableRage: Go ahead, just try to hurt/kill anybody he cares about. '''[[SchmuckBait WE DARE YOU]]'''.
* VigilanteMan: He was the was the one who killed Ming Ming Trin, the drug dealer that sold the heroin his sister OD'd on. Also killing many of the Triads also counts too.
* YourCheatingHeart: He eventually gets called out on the multiple liasons he can have by Tiffany and Not-Ping, who dump him not long after (though Not-Ping [[MasterOfTheMixedMessage still asks him to call her]]).

!!Jackie Ma (Voiced by Edison Chen)

A low-level street affiliate to the triads, Jackie is Wei's childhood friend from the Old Prosperity project who knows several of the Water Street Gang members, but is not considered part of the group. After being arrested from a drug deal gone bad, to which Wei was undercover, he meets Jackie in lock up, reminiscing about the old days. Wei offers himself as extra muscle for the Water Street Gang and Jackie goes to put in a good word for him with gang leader Winston.

Throughout the game, Jackie is enamored with the glamorous lifestyle of the triads, wishing he could be a part of it.

* BecauseYouWereNiceToMe: Jackie reminds Wei during their first outing for the Sun On Yee in the night market that Wei was the only other kid who was nice to Jackie when they were growing up, and that their friendship means more to him than a boss-subordinate relationship (such as Jackie's to Winston), though this is made moot when [[spoiler:Wei formally succeeds Winston as Red Pole, officially confirming his inheritance of the Water Street Boys]].
* BreakTheCutie: Jackie has a lot of ambition about becoming a Sun On Yee, but even from the very beginning the player can kind of tell he probably wouldn't be cut out for the ruthlessness of being a full-on career criminal. Slowly but surely his veneer cracks and he becomes less-and-less enthralled by the lifestyle until finally it breaks [[spoiler:after he's buried alive and turns totally cold.]] His enthusiasm is completely shattered after that, as is his worldview. [[FromBadToWorse And can you believe that isn't even as low as it goes for him]]?
* CruelAndUnusualDeath: [[spoiler: Is disemboweled and hung...[[PlayerPunch and this is after Wei saves him from being buried alive]]]].
* DamnItFeelsGoodToBeAGangster: Subverted later down the line, [[spoiler: after Jackie performs his first kill in order to be initiated into the Sun On Yee]], and completely gone after [[spoiler:the mob war between the Water Street Boys and the "Big Smile" Lee-backed 18k]].
* DistressedDude: Played with in one mission, where Jackie gets locked inside an 18K truck with an angry 18K member after a heist gone wrong. When Wei stops the truck and bust open the back to save him, he discovers [[TookALevelInBadass he curbstomped his opponent alone and walks off just fine]].
* IJustWantToBeBadass
* KickTheDog: Wei's designated "dog", beginning when he's roughed up by one of Dogeyes' men early in the game. The kicks get ''much'' harder along the line.
* TheLancer
* ThePeterPrinciple: Jackie is a mildly competent low-level crook. But he clearly doesn't have the stomach or skill to handle the higher echelons of crime.
* {{Retirony}}: [[spoiler: Shortly after he starts dropping hints about getting out of the Triads and starting a new life with Jiu Mei he's kidnapped, tortured and killed]].
* StuffedIntoTheFridge
* TheseHandsHaveKilled: He's plagued by guilt after his first killing.
* YankTheDogsChain: [[spoiler:Rescuing Jackie from his live burial at least points to a possible happy ending for him, even though he's severely burnt out on being a gangster. However Big Smile Lee has Jackie brutally murdered a little while later, using him as bait in order to get Wei to come to him.]]

!!Winston Chu (Voiced by Parry Shen)
->''"We're a family. Family has to stick together."''

Winston is the leader of the Water Street Boys gang, a subsidiary faction of the Sun On Yee. He's also a Sun On Yee red pole who controls North Point. Headstrong, cocky and brutal (it's implied steroids has something to do with it), Winston grew up in the Old Prosperity housing project with numerous Sun On Yee members, including Sam "Dogeyes" Lin. Although he mentions the two of them were close, the triad lifestyle has turned them into bitter enemies. Engaged to long-time girlfriend Peggy Li, he runs the Water Street Boys out of the kitchen of his mother's restaurant "Golden Koi". Winston has been under fire from Dogeyes' Jade Gang repeatedly, stealing his businesses and territory from the Night Market for over a year before the game takes place.

* BenevolentBoss: He requires loyalty, but, as long as you stay loyal, he'll treat you like his own flesh and blood.
* BlingBlingBang: Winston owns a gold-plated Desert Eagle. During one story event, he uses it to threaten Wei after one of his drug dealers accuses Wei of being TheMole, but ends up killing the accuser instead. Wei picks it up [[spoiler: after Winston's death]] to tell Big Smile Lee's henchmen "Ponytail" he doesn't feel in any way intimidated by Lee's threats. And then starts with it in the next mission.
* CruelAndUnusualDeath: [[spoiler:Shot up into Swiss cheese ''on his wedding day'']].
* DumbMuscle: He and his gang are all known as a couple of dumb brutes, with his HKPD field report describing him as "ambitious without the brains to achieve his goals", as of 2010 (almost two years before the events of the game) he was described as sometimes unable to "even master street-level criminal conspiracies", and his lack of sophistication means that even though he answers directly to [[TheDon Uncle Po]], other red poles eclipse Winston in power and influence.
* GangBangers: How Winston's Water Street Boys gang is portrayed, though this has essentially created a glass ceiling for them [[spoiler:and Wei's predecessor as undercover, Charlie Ho, had written off the entire gang as unable to move up]].
* HonorAmongThieves: Believes that the only people who they can rely on in their line of work are their fellow Water Street boys and places a clear value on loyalty. He even goes as far to say that fellow gang members are like blood to him. A sentiment echoed by his fiancee. [[spoiler: Sadly for them Dogeyes does not share this sense of honor.]] The flipside to this is that he is also quick to kill anyone he suspects to be a traitor or a snitch.
* JerkWithAHeartOfGold: Besides his relationship with his fiancee and his mother, in his first meeting with the adult Wei he has the decency to apologize for his overtly sexual attitude towards Wei's sister after Wei mentions that she's dead, [[BlackAndGreyMorality clearly setting him apart from Dogeyes]].
* MommasBoy: He is still very close to dear old mom, and operates his gang out of her restaurant.
* MoralityPet: Peggy Li
* NeverSpeakIllOfTheDead: When Wei tells him that his sister died years ago, Winston apologize for the inappropriate comment he made about her moments ago.
* TogetherInDeath: [[spoiler: He's gunned down at his own wedding along with Peggy, dying from gunshot wounds not long after his wife.]]
* WeUsedToBeFriends: He and Dogeyes used to be close until he was [[NoodleIncident betrayed]]. Now they're at each other's throats.

!!Conroy Wu (Voiced by Robin Shou)

Another member of the Water Street Gang born in the Old Prosperity projects, Conroy initially shows hostility and suspicion of Wei being an undercover cop. In one mission, Conroy mentions the fate of a previous gang member who turned out to be an undercover cop before him, and requests Wei to commit murder in order to prove himself. However, after Wei happens to kill rival muscle in the process of kidnapping drug maker Siu Wah, Conroy apologizes to Wei for his animosity and begins to cooperate with him.
* TheDragon: To Winston, though his being promoted signaled that the Water Street Boys had become mere {{Gang Bangers}}.
* DumbMuscle: So much so that according to an informant, Conroy actually makes Winston look ''worse'' (instead of "better by comparison") since he cements other red poles' belief that "Chu cannot attract or cultivate effective subordinates"; Conroy is also "a frequent steroid and drug user and has few skills beyond brute force violence".
* FireForgedFriends: After Wei proves himself to Conroy in the warehouse raid, he instantly apologizes for his previous behavior, seeing Wei as a true ally. After Winston's death, Conroy becomes Wei's number 2, and they get along pretty well.
* GangBangers: Just like the rest of the gang, described by [[spoiler:the late Charlie Ho]] as "pure thug".
* JerkWithAHeartOfGold: He's kind of a standoffish bully at first, but only out of loyalty to the Sun On Yee. He's actually one of the more honorable members of the organization.
* ProperlyParanoid: He is suspicious about Wei being a potential cop, but underestimates him and how far he's willing to go to preserve his cover.
* TeethClenchedTeamwork: Initially with Wei.
* UndyingLoyalty: First to Winston, and then to Wei once he takes over.
* WrongGenreSavvy: He believes a reluctance to kill and Wei's background are similar to that of previous undercover cop. However when Wei kills several rival thugs during the warehouse shootout, Conroy believes he's proven himself. However he doesn't understand what [[TheMole kind of ally]] Wei is or consider that if a police officer stumbled onto that scene he'd likely be forced to use his sidearm in self-defense.

!!Ricky Wong (Voiced by Ian Anthony Dale)

Ricky Wong is a member of the Sun On Yee who assists Wei in his search for Johnny Ratface, [[spoiler: the man who assassinated Winston and Peggy during their wedding]], and makes several appearances as "Big Smile" Lee's liaison with Sonny Wo. He is also quite aware of the dramatic changes within the triads and its codes. Ricky is currently in a relationship with film starlet/singer, Vivienne Lu.
* BadassInANiceSuit: Never seen out of his black suit.
* CharacterDevelopment: When Wei first meets him he seems very aloof and cocky, but as the game goes on he gets more anxious and emotional.
* FriendlyEnemy: He's one of Lee's enforcers, which ''should'' put him squarely at odds with Wei. Instead, they strike up something of a friendship, and they work together several times.
* InLoveWithTheGangstersGirl: He's the gangster in question. Subverted in that she's sleeping around with other guys at the behest of Sonny, although [[spoiler:that's how she and Ricky got together in the first place]].
* NiceGuy: He's very friendly, and he has a strong moral code. He also never strays from his girlfriend, despite Sonny constantly providing opportunities for him to do so.
* ScrewThisImOuttaHere: [[spoiler:His response to the situation with Wei and "Big Smile" Lee. With a little prodding, of course]].
* TokenGoodTeammate: He's pretty much the only member of Lee's entourage that isn't a complete bastard.
* UndyingLoyalty: Even in the face of what Sonny puts him through regarding his girlfriend, he still remains loyal. [[spoiler: Once Sonny's behind bars and the conflict with Big Smile Lee escalates he decides to simply leave, rather than take sides.]]

!!Sam "Dogeyes" Lin (Voiced by Ron Yuan)

A Sun On Yee red pole and leader of the Jade Gang, another Sun On Yee subsidiary faction, Dogeyes is Winston's archrival in North Point. Despite being close friends with Winston as children, Dogeyes resented him for having a better environment and mother, whereas his mother died and his father was abusive. It was he who lured Wei's sister Mimi into drugs and prostitution.
* AssholeVictim: [[spoiler: No tears are shed when Mrs. Chu turns him into mince meat]].
* CruelAndUnusualDeath: Overlaps with [[spoiler: ImAHumanitarian. Before being butchered by Mrs. Chu, she feeds him soup made from Johnny Ratface's remains]].
* DiscOneFinalBoss: He's disposed of mid-way through the game.
* DirtyCoward: When Wei finally is sent after him, Dogeyes elects to [[ScrewThisImOuttaHere run away]] while putting [[WeHaveReserves as many mooks as possible]] between him and Wei. When cornered, he attempts to explain away his actions as [[NothingPersonal only business]] and warns that killing him will start a war. [[spoiler:It doesn't work]].
* DoNotCallMePaul: Dogeyes' reaction when Mrs. Chu calls him "Sammy."
* ImAHumanitarian: Albeit in an unwilling manner: [[spoiler: the soup Mrs. Chu cooked up for him? She made it with what's left of Johnny Ratface after she was done hacking him to pieces]].
* {{Greed}}: An informant revealed that Dogeyes was paid off to encroach on Winston's Water Street Boys instead of the 18k (''not'' Sun On Yee and thus fair game) in Dogeyes' own territory, and that Dogeyes was "too greedy to say no and too stupid to be afraid of discipline by Sun On Yee elders."
* IronicEcho: After begging with Wei that what happened to his sister was "just business" and nothing personal (to set Wei up for an ambush), [[spoiler:Wei says the same thing when Dogeyes begs for real to be saved from Mrs. Chu.]]
* {{Jerkass}}: Right in his first appearance, he taunts the just-returned Wei about having [[spoiler:used Wei's late sister Mimi for sex]].
* HateSink: Dogeyes' role is to be a despicable asshole and a constant thorn on Wei's side so that his inevitable downfall will be all the more satisfying.
* KickTheSonOfABitch: [[spoiler:And he [[AssholeVictim deserves it]]]].
* NiceHat: He's always sporting a trilby.
* NiceJobFixingItVillain: As noted on the main page, he sets himself up to be screwed by [[spoiler:having Winston killed]], as [[spoiler:Wei's immediate assumption of leadership (indirectly sidelining Conroy)]] only makes the Water Street Boys gang ''far'' more legitimate and dangerous than they had been [[spoiler:under the late Winston's command.]] It's stated elsewhere in the game that hierarchy is everything to the triad gangs, and Dogeyes clearly wasn't observing the hierarchy of the Water Street gang while plotting or aware that [[spoiler:Wei had already secured his position before the hit ''and'' rescued Uncle Po during the massacre]], so instead of fracturing the Water Street Gang, Dogeyes indirectly [[spoiler:united that gang behind Wei ''with'' Uncle Po's endorsement]].
* SmugSnake: His primary purpose is to be a douchebag who eventually gets what's coming to him.
* WeUsedToBeFriends: With Winston; Mrs. Chu even mentions that Dogeyes used to eat at her restaurant and addresses him by his childhood nickname "Sammy".
* [[YourMom Your Sister]]: When he [[spoiler: comes back as a ghost in the Nightmare at North Point DLC, he tells Wei he just had sex with his sister in Hell]].

!!Henry "Big Smile" Lee (Voiced by Tzi Ma)
->''"I am the strongest. I am the most feared. I say I should be chairman."''

Henry "Big Smile" Lee is a red pole of the Sun On Yee, with the heaviest ties to drugs, prostitution and pornography in the triad. Considered the most powerful red pole inside the Sun On Yee, he is disliked by the other red poles and many rank and file members of the triad. Lees power stems from his willingness to use extreme (even by triad standards) levels of violence and the overwhelming amount of liquid cash generated by his various business ventures. Because of this, Lee believes himself to be the natural successor to the leadership of the Sun On Yee once current chairman, David Wai-Lin "Uncle" Po, steps down or passes away.
* AmbitionIsEvil: He is the most powerhungry and vicious of the Red Poles.
* BigBad: [[spoiler:Interestingly it doesn't even come up until the final act. Up until then it looks like if he does become an enemy, you'll be powering through him to get to someone else (possibly the head of the 18K, since it appears he was in cahoots with them). Instead Lee himself becomes the final obstacle when he makes things personal by having Jackie murdered.]]
* CruelAndUnusualDeath: [[spoiler:Death by ice chipper]]
* GlasgowGrin: Has half of one, with a huge scar on his face that starts at his chin and extends past the left side of his mouth, giving him an oddly appropriate perpetual sneer.
* GoodScarsEvilScars: His GlasgowGrin pretty much gives it away that he is a vicious man who is not to be trusted.
* MeaningfulName: "Big Smile" in Cantonese is a slang on the term "older brother" or "boss". Given how being Chairman is all he really wants, [[spoiler: him being the BigBad was likely [[{{Foreshadowing}} foreshadowed]] right off the bat]]. It may also be a reference to the half-Chelsea Grin carved on his face. Or, given the Chinese love for clever wordplay, both.
* MoralityPet: According to WordOfGod, he's actually motivated by the fact he wants his daughters in America to be obscenely rich [[spoiler:no matter who else gets hurt in the process]].
* MoreDakka: Big Smile Lee's plans... lack subtlety.
* TheStarscream
* TokenEvilTeammate: While the other heads of the Sun On Yee tend to lean towards white-collar crime such as money laundering, "Big Smile" Lee is reputed as a thug who who retains ties to prostitution, porn and the drug industry. His files indicate that Uncle Po keeps him around to do the real dirty work.
* WaistcoatOfStyle: He's always wearing a waistcoat.

!!Sonny Wo (Voiced by Chin Han)
->''"You take good care of my little starlet. Go ahead and fuck her if you want! Just don't damage the goods!"''

A depraved pervert who is responsible for laundering the Sun On Yee's via the entertainment industry. He forged his media empire by launching the careers of countless Hong Kong popstars. Hated by pretty much everyone who isn't Big Smile Lee, it's made abundantly clear that absolutely no one likes spending time around him.
* CorruptCorporateExecutive: His production company launders Sun On Yee's money, and if any of his starlets fail to perform they end up working in the triad's prostitution business.
* TheFriendNobodyLikes: Lee is the ''only'' person who doesn't have any sort of problem with Sonny. Wei outright says to King that he thinks Sonny is an annoying clown and King completely agrees.
* HateSink: He has absolutely no redeeming qualities.
* HoistByHisOwnPetard: His exploitation of Vivienne Liu blows up in his face when [[spoiler: her apartment is bugged and Sonny is implicated on record.]]
* {{Jerkass}}: He is quite an obnoxious dick and a huge pervert to boot. The people close to him pretty much only (barely) tolerates his company because he knows how to make money.
* ThePeepingTom: It is very heavily implied that he prefers getting his jollies from watching young pretty women having sex with other men.
* NecessaryEvil: This is the general opinion of him among the Sun On Yee. He's a repugnant jackass, but he does bring ''a lot'' of capital.
* NoSocialSkills: Loudly discusses his dirty fantasies in the same room as the person that fantasy is about, will offer to prostitute one of his singers out to a business partner ''while that singer is standing right there'', will sometimes make blunt sexual advances right to someones face -- the list goes on an on...
* YouHaveOutlivedYourUsefulness: Any singer who argues with him, or even just fails to top the charts is quickly handed over to Big Smile Lee and used as a prostitute.

!!"Broken Nose" Jiang (Voiced by Elizabeth Sung)
->''"I believe in harmony. Balance. Peace. And I don't mind spilling a little blood to achieve it."''

Another Sun On Yee red pole, Broken Nose Jiang is a successful feminine prescence in a masculine-dominated socity who distrust, use and abuse others of her gender. Undercover investigators have been unable to determine her real name, and she has crafted a reputation based on fear of her alleged ruthlessness towards threats to her power base. Considered Big Smile Lee's arch-rival, Jiang is less than supportive of Sun On Yee's prostitution and pornography production rings.
* ALighterShadeOfBlack: While she's still a ruthless member of the Sun On Yee, she's practically a good guy compared to "Big Smile" Lee.
* BewareTheNiceOnes: As diplomatic as she is, her rise to the position of red pole was getting rid of the competition by murder.
* TheChessmaster
* DragonLady: Overlaps with CoolOldLady.
* KnownOnlyByTheirNickname: Even the police don't know her first name.
* LesserOfTwoEvils: When compared to "Big Smile" Lee.
* PragmaticVillainy: In her first meeting Wei, she claims that there are much more profitable (probably not legal) ways to make money than "Big Smile" Lee's archaic business of forcing women into prostitution and pornography if she were elected as Chairman.
* TheSmurfettePrinciple: The only named female member of the Sun On Yee. Justified given how hard it would be for a woman to get anywhere near her level of power. "Big Smile" Lee addresses this matter while they're in crisis mode over picking a new chairman.
* XanatosSpeedChess: Pulls this when [[spoiler:after "Pockmark" Cheuk refuses the position of temporary Chairman while Uncle Po convalesces, she recommends "Two Chin" Tsao before "Big Smile" Lee can nominate himself]].
* YouWillBeSpared: [[spoiler: Jiang sends Wei evidence against Pendrew, addressing Wei as "Officer Shen", and at the end of the main story she tells "Pockmark" Cheuk that Wei is to be left alone, as a token of his loyalty to Uncle Po's vision of the Sun On Yee and for helping her becoming the new Dragon Head by removing the competition]].

!!Howard "Two Chin" Tsao (Voiced by Conan Lee)

Howard "Two Chin" Tsao is a Sun On Yee red pole with a large estate in Kennedy Town and is Uncle Po's nephew. After [[spoiler:Uncle Po is left hospitalized, Two Chin became temporary Chairman of the Sun On Yee]]. An extremely superstitious man, Tsao delves deeply into ''feng shui'' and relies on luck. According to Old Salty Crab, Tsao often gambled and rarely won, losing his money fast.
* AddledAddict: [[spoiler:After Wei and Old Salty Crab trash his house, he's completely succumbed to his heroin addiction and thus deemed unfit as chairman]].
* BeliefMakesYouStupid: Delves so heavily into ''feng shui'' that one mission involves messing with his home to spook the hell out of him [[spoiler: in order to incapacitate him as temporary Chairman of the Sun On Yee, so as to pave the way to elect a formal Chairman]]. Old Salty Crab notes that regardless of whether or not he actually buys into the stuff, the fact that someone broke into his house is still enough to drive him over the edge
* DrugsAreBad: He's stated to have a heroin habit, which "Broken Nose" Jiang and Wei end up exploiting.
* FatBastard: He's named "Two Chin" for a reason. He's less malicious than many members of the Sun On Yee, but he's still a crime boss.
* TheGambler: And not a very good one, as he's constantly losing all his money.
* {{Gaslighting}}: He becomes a victim of this due Jiang wanting him removed as temporary Chairman non-violently lest he grows too comfortable in his position or "Big Smile" Lee kills him for the position.
* PunnyName: His last name is pronounced like "sow", i.e. a pig.
* UnwittingPawn: [[spoiler:Jiang only recommends he be placed in power so as to occupy the Chairman role and keep "Big Smile" Lee out of it. She has no intention of letting him actually act as the full Chairman and immediately sets about trying to discredit him and bring about a proper nomination.]]

!!David Wai-Lin "Uncle" Po (Voiced by Creator/JamesHong)
->''"Loyalty, discretion, used to be more common."''

The dragon head and Chairman of the Triad organization, Sun On Yee, Uncle Po has cultivated an image of a negotiator and business-oriented pragmatist. But this "reasonable" visage stands in stark contrast to Pos criminal history: his rise to Chairman was marked by extreme violence at every stage. He revitalized the triad's murder-for-hire business and is suspected of being the brains behind its alliance with Sonny Wo. To keep his hands clean, he appoints Big Smile Lee to handle the day-to-day financial operations, yet much of the profit ends up in Po's pockets.

Uncle Po's hold on the Sun On Yee remains unchallenged, with certain red poles simply waiting for their opportunity to seize his position after he retires or dies.
* AffablyEvil: Is capable of horrible crimes, yet he seems genuinely to treat it as a family business, praising Wei as a foot soldier possessed of now-uncommon loyalty and discretion [[spoiler:and never bringing up Wei's "disappearing" Dogeyes]].
* BewareTheNiceOnes: His rise to Chairman of the Sun On Yee was bloody, according to the police reports.
* TheDon: As the head of the Sun On Yee.
* EstablishingCharacterMoment: In the mission where we are introduced to him, Winston has been summoned to meet him and he's completely scared out of his mind, spending the entire trip telling Wei his last wishes. When they finally arrive we see this polite old man gently forgiving Winston's actions (see ReasonableAuthorityFigure below), praising Wei's good performance and deciding to reward him. However when Wei tries to politely decline, Uncle Po gives Wei a relatively quiet yet sharp "Don't argue with me", which immediately silences Wei. A perfect indication that Po can be quite reasonable and polite but you do ''not'' want to defy him.
* EvenEvilHasStandards: Expresses extreme disgust with the factions that [[spoiler:butchered everybody at Winston's wedding and shot him]]; his tone during this hints he would never have stooped to that level.
** He may not be cool with drug dealing to children: after a dealer refused to stop, [[spoiler:"making an example" of that dealer becomes Wei and Jackie's initiation challenge]].
* EvilOldFolks: The leader of the Triad, and evidently one of its oldest members. [[AllThereInTheManual According to his bio, his capacity for brutal violence is extreme, even by triad standards.]]
* ReasonableAuthorityFigure: Absolves Winston and the Water Street Gang for their retaliation against Dogeyes' Jade Gang, since the latter was the one provoking Winston, and compliments Wei's effectiveness as a foot soldier [[spoiler:before confirming him as Winston's successor]].
* SickbedSlaying: [[spoiler:His old cohort, Thomas Pendrew, kills him while he is bedridden by injecting lethal chemicals into his IV bag]].

!!Roland Ho (Voiced by Robin Shou)
->''"People always want to borrow. If they ever learned to live within their means, I'd be screwed."''

Roland Ho is a money lender, loan shark and debt collector. Wei can accept jobs from Roland after he is referred to him by Uncle Po. Roland's missions involve collecting unpaid debts and intimidating his debtors. Notable for over-the-phone quest givers, Wei seems to actually consider Roland an acquaintance of sorts rather than a just another business partner.
* FauxAffablyEvil: [[spoiler: So good at hiding his [[JerkAss utter lack of standards]] that Wei even let his guard down and befriended him.]]
* JerkAss: Becomes painfully obvious after [[spoiler: Samson Gao is DrivenToSuicide by his massive debt, and Roland wants to shake down his widow to see if he had life insurance]]. Wei understandably refuses to keep working for Roland after this.
* LoanShark

!!Old Salty Crab (Voiced by Tzi Ma)

One of the only veteran triad members who still does his own dirty work, he is somewhat of a prankster, and often gets creative when doing work for the triad. Extremely spiritual, but only for pragmatic reasons, his expertise on Chinese mysticism often becomes surprisingly handy.
* TheAce: If his stories are to be believed, back in his glory days he could have given Wei a run for his money.
* TheAllegedCar: His "Crab Car", which was originally a top-of-the-line sports car, looks like it's seen much better days, but it's still a fast little number.
* AscendedExtra: Only appears in one mission and a phone call, but then gets revealed as Not-Ping's uncle in Nightmare on North Point.
* EvilCounterpart: Only "evil" by virtue of being a criminal, as he's actually quite friendly and helpful to Wei, but he's the man Wei could have ended up as if he'd spent his whole life in the triads instead of becoming a cop (and let himself go physically).
* FatBastard: With far more emphasis on the "fat" than the "bastard". His weight may have something to do with the events that earned him his nickname (see below).
* GayMoment:
-->'''Old Salty:''' You're pretty and talented.\\
'''Wei Shen:''' What?\\
'''Old Salty:''' I said you're pretty talented.
* InSeriesNickname: Earned the name "Salty Crab" when, rather than simply accept valuables from a debtor restaurant owner otherwise unable to make payments, he requested that the man give him free food every day as an alternative -- and subsequently [[TheTrickster brought the restaurant to the brink of bankruptcy by ordering the most expensive thing on the menu en-masse every day]] (which was "Salt Crab"). The "Old" was tacked on when, well, [[ExactlyWhatItSaysOnTheTin he became old]].
* InsultBackfire: A mild example:
-->'''Wei Shen''': You're a strange guy, Old Salty Crab.
-->'''Old Salty''': Thanks. That means a lot to me.
* KnownOnlyByTheirNickname
* TheMentor: Teaches Wei about Chinese mysticism to help him in his fight against Smiley Cat and his undead army.
* [[PragmaticVillainy Pragmatic Morally Ambiguous]]: His reason for believing in Feng Shui isn't for the sake of tradition, culture, or even that he thinks it's probably real -- It's so if the underworld ''IS'' truly real, then Feng Shui will keep all the people he killed from exacting revenge from beyond the grave.
* TheTrickster: When told to scare someone, he doesn't just leave a threatening note or phone-call, he gets creative (as in; convince the target the dead want to kill him).
* UnmanlySecret: If the dialogue in his quest when the player hijacks a Bisai is anything to go by, he secretly wants to buy a tiny little smart car of his own after the Crab Car finally breaks -- which is probably why he mistreats the Crab Car so badly.

!!Liu Shen Tong

The Sun On Yee's chief interrogator and TortureTechnician. Whenever someone greatly displeases the Triad, such as [[spoiler:being found out as an undercover cop]], the offending party is sent to him for punishment. Despite his calm, even affable nature, he clearly takes a dark joy in torturing his victims.
* BuriedAlive: His preferred method of disposing of his victims once he's done with them.
* TheDragon: To Big Smile Lee.
* TheDreaded: He's infamous within the Sun On Yee for his brutal torture methods.
* EarlyBirdCameo: Players with good hearing will notice that he is mentioned by Vincent as early as the third mission, and is whispered about by mooks even earlier.
* FauxAffablyEvil: [[spoiler:Is completely civil and polite to Wei...as he drives an ice pick into his leg.]]
* HoistByHisOwnPetard: [[spoiler:Stabbed clean through the chest with his own machete.]]
* KnifeNut: Comes with being in the Triads. He favors the scalpel when torturing his victims, but when the time comes for actual combat, he breaks out the machete.
* MacheteMayhem: Wields a massive one.
* NotSoStoic: He starts out confident and gloating, though still rather civil and avoiding any profanities [[spoiler: while torturing Wei]], with his voice remaining slow and almost monotonous. [[spoiler:As Wei is about to kill him]], he descends into [[ClusterFBomb Cluster F-Bombs]] and ranting about how [[spoiler:[[YouHaveNoChanceToSurvive Wei is doomed to fail to stop Lee]]]].
* PreAsskickingOneLiner: [[spoiler: Delivers one to Wei at the start of their fight]]. His tone of voice really sells just how displeased he is.
-->'''Tong''': I suppose I should be impressed; you defeating my men like that. I... '''am ''not'''''. Now... where were we?
* SharpDressedMan: Wears an [[EvilWearsBlack all black]] suit and black leather gloves. It's such a nice suit that [[spoiler:Wei steals it from him after he kills him]].
** BadassInANiceSuit: See his one liner, he backs the talk too, having two OneHitKill move.
* TortureTechnician: Sun on Yee's expert although it's not for information, just to send a message about what happens to undercover cops.

!!Vincent (Voiced by Osric Chau)

A member of the Water Street Gang members, he is initially distrustful of Wei, but grows to trust him after Wei proves himself. [[spoiler: Later murdered for his organs by an 18k member.]]
* AscendedExtra: Gets more development in the Nightmare at Northpoint DLC than in the game.
* BecauseYouWereNiceToMe: When he [[spoiler: comes back along with the other dead Triads in the DLC, he chooses Wei to haunt because he wants to talk with his old friend again]]
* DumbMuscle: Like most of the Water Street Gang.
* OrganTheft: [[spoiler: The cause of his murder]]
* TheFriendNobodyLikes: While he is [[spoiler: "haunting" Wei]] he remarks that even when [[spoiler: he was still alive]], people tended to avoid him.
* ThoseTwoGuys: With Duke.
* TrademarkFavoriteFood: Noodles.

!!Tran Ma (Voiced by Feodor Chin)

Jackie's uncle and owner of the first vehicle chop-shop in the game, he provides Wei and Jackie with the vehicles they need to pass the initiation missions. After that, he fades into the background as one of the people Wei can call to receive missions for quick cash. He's notable only because a strange glitch rendered him both killable and [[BerserkButton aggressive]].
* BerserkButton: Drive too recklessly around his lot and he may run after Wei with a wrench. It's probably not intentional.
* DeathIsCheap: If the player lure him far enough, you can throw him onto spikes or into a tub of electric eels -- And yet the next time you visit his chop-shop he will be perfectly unharmed.
* DemotedToExtra: Originally a minor character who provides Wei and Jackie with cars as they try to get initiated, he vanishes into the background [[GameplayAndStoryIntegration the moment you unlock the better car dealers]].
* GameplayAndStorySegregation: He is not only damageable, he is easily killable as well. And unlike other quest givers Tran will actively chase Wei if angered or attacked.
* PunnyName: Probably a play on "Transmission", AKA a part of a car.
* SuicidalOverconfidence: Will attack ''Wei''.

!!Doctor Tang

The Sun On Yee's chief scientist (yes, they're a gang with a science division, that's Hong Kong for you). Develops various gadgets to help the mob commit crimes and ropes Wei into testing some of them.
* AbsentMindedProfessor: He's a bit of a goof, which may or may not explain why he's working for the mob rather than in the legitimate scientific community.
* AscendedExtra: He only appears in a couple of side quests in the main game but takes a starring role in the ''Wheels Of Fury'' DLC.
* ReluctantMadScientist: He doesn't have the same lust for money, power or respect that most triads do. He just wants somebody to fund his research.

!! Smiley Cat/Big Scar Wu
->"You give a guy anything less than a proper burial, chances are he's gonna come back as a ghost. You turn him into cat food, it's pretty much guaranteed."
-->--Old Salty Crab.

The BigBad of the ''Nightmare in North Point'' DLC.

In the days before Wei returned to Hong Kong one of the Sun On Yee's most ruthless members was a man by the name of Big Scar Wu, who was feared as much by his fellow gang members as by his enemies. Eventually, Uncle Po decided that he was too violently insane ''[[EvenEvilHasStandards even for the triads]]'' and ordered his death, having him run over in a staged "traffic accident", then stabbed 42 times for good measure. Finally his body was disposed of in a pet food factory and he found his final resting place in the bellies of the cats of Hong Kong.

But his story doesn't end there. After he got to the underworld his fellow dead gangsters mocked him mercilessly for the undignified manner of his death, refusing to call him by his street name, instead referring to him by the name of the catfood brand he was made into. Thus, Smiley Cat was born.

After many years in Hell, growing even more bitter and insane than he was in life, he has assembled an army of demons, vampires and hungry ghosts and returned to Earth to seek revenge on the Sun On Yee.
* AxCrazy: The reason why Uncle Po ordered his death, as he was declared too vicious [[EvenEvilHasStandards even for them.]]
* AccidentalMisnaming: Even his army of demon-possessed gangsters call him Smiley Cat, much to his annoyance.
* CoolMask: Wears a creepy mask depicting a smiling cat face.
* GotMeDoingIt: He's been called Smiley Cat so much that at one point he even calls himself it. He quickly corrects himself.
* InsistentTerminology: It's Big Scar Wu!
* LargeHam
* RasputinianDeath: How the Sun On Yee killed him in the first place. See the above description.
* TigerVersusDragon: Has tiger stripe tattoos in contrast to Wei's dragon ones. Better, he's associated with the color white, which represents death in Asian cultures, making him a perfect Bai Hu (white tiger) to Wei's (who, as a policeman is often dressed in blue) Quing Long (blue dragon).


[[folder: Hong Kong Police Force]]
!!Superintendent Thomas Pendrew (Voiced by Tom Wilkinson)
->''"Wei, I know who you are. You're just like me. You do what must be done."''

A 28-year veteran of the Hong Kong Police Force, Superintendent Pendrew is the one who brought Wei Shen to Hong Kong for the undercover operations into the Sun On Yee. Having built his career by taking down the triads, Pendrew has plenty of experience in the field, much of which began years earlier when he took down "the Three Tigers of South Point" former, prominent leaders of the Sun On Yee. With Uncle Po the only one remaining of the triad's leaders, Pendrew will do what's necessary, even if it means bending a few rules, to bring it down and move on with a clear conscience.

As Wei continues his duty undercover, Pendrew insists to be in charge of Wei's job and won't hesitate to cut his operative loose if he crosses a certain line.
* BigGood: Initially presented as this, but [[spoiler:averted upon the discovery that he's been working with Uncle Po.]]
* DirtyCop: [[spoiler:The ending and his file reveals that he's been working with Uncle Po for a long time to deal with their respective enemies and thus get both of them promoted]].
* EvilBrit: [[spoiler:The only British member of the main cast, and as it turns out, was collaborating with Uncle Po, until he kills Po to cover up their dealings. He also tries to have Wei killed by outing him as a cop to Big Smile Lee.]]
* LaserGuidedKarma: [[spoiler:He ends up getting arrested and being sent to prison with many of the criminals he put away, who now know that he's the one who killed Uncle Po]].
* KnightTemplar: His only concern is bringing down the Sun On Yee, even if it means planting evidence and letting his undercovers flagrantly violate procedure to do so. [[spoiler:He later turned out to be a dishonest person who's only serving his own needs. Luckily, Wei had enough of his manipulative lies and sent his ass to jail, which is rightfully a death sentence considering how many people that want him dead are in there.]]
** His IA investigation file specifically mentions that he's not getting bribes for his cooperation with the Triads - apparently it really is about serving "the greater good" as far as he's concerned.
* NiceJobFixingItVillain: This man is the sole reason the game is called [[MeaningfulName Sleeping Dogs.]] Before he sent in Wei, the Sun On Yee was on the brink of collapsing under it's own mismanagement and interfactionary tension. Wei, a man with his own personal drama with the Sun On Yee waiting to be kicked off, not only raises it from it's slumber, culls the poisonous parts of the organization, and makes it the strongest Triad gang in Hong Kong, [[spoiler: but also makes sure the dog bites and gets Pendrew sent to prison.]]
* NotSoDifferent: [[spoiler: Gets called out on having risen to the top by similar means from Uncle Po -- after which Pendrew poisons his IV line]].
** Says this to Wei earlier in the story.
* PariahPrisoner: [[spoiler:His fate in the end, thanks to the evidence sent to Wei by "Broken Nose" Jiang.]]
* PrecisionFStrike: [[spoiler:Upon learning that he'll be going to prison as the man who killed Uncle Po]], he declares that a "Fucking death sentence".
* WalkingSpoiler: It is rather hard to describe him without mentioning that [[spoiler:he is a DirtyCop who collaborated with Uncle Po in the past and betrays Wei to Big Smile Lee near the climax.]]
* YouHaveOutlivedYourUsefulness: [[spoiler:He kills Uncle Po upon being promoted to Interpol in order to eliminate any evidence of his dirty work. He also rats out Wei to "Big Smile" Lee after he proves to be too much of a nuisance]].

!!Raymond Mak (Voiced by Byron Mann)

Wei Shen's handler during his undercover into the Sun On Yee, Raymond Mak warns Wei not to underestimate the triad, in spite of the differences between his experience with the American gangs back in San Francisco. Over time, Raymond begins to question Wei's mission, fearing he will turn it into nothing more than a personal vendetta against the Sun On Yee. Despite the relay of information from Wei, Raymond continues his duty as a handler, while Pendrew assures him that Wei is perfectly capable of completing his tasks.
* ByTheBookCop: In contrast with [[CowboyCop Wei]], Raymond is always calling him out for his recklessness and worries about him [[BecomingTheMask going too far into his role]].
* ReasonableAuthorityFigure: Frequently calls Wei out but his objections are fairly reasonable since they're supported by in-game logic. He also admits to Wei at one point that he sympathises with him and that he might be right in him being the best chance to bring down the heads of the triad, but he maintains that he still believes that Wei has gone too far with some of his actions and is bringing himself in too much danger.
* VerbalTic: Has a habit of ending sentences with 'alright?'
* WhatTheHellHero: Seems to believe Wei is going over to the Triads. Understandable since Wei is talking [[spoiler: about a gang war to avenge his dead Triad buddies and asks a criminal to be released because he is his friend.]]

!!Inspector Jane Teng (Voiced by Creator/KellyHu)

A proud, young officer of the Hong Kong Police Force, Inspector Jane Teng is aware of making compromises, finding it much difficult to do so at certain times with such grace. Politics from the department continuously sideline her requests, who forces her to maintain a stoic, cold facade. When Wei Shen is arrested in the process of assaulting and extorting a Dogeyes-affiliated drug dealer, Teng is told of his undercover operations. Despite the unfriendly alliance (alongside being forced to tolerate Wei's actions), after he offers to support her operations in the process, she assigns him unsolved cases to help bring down criminals around the city.
* ByTheBookCop: She refuses to let Pendrew take away Wei during the interrogation since he was spotted fighting and he is on her custody. Pendrew has to exasperatedly shout he is an undercover cop instead of trying to intimidate her with hierarchy.
* DefrostingIceQueen: She dislikes Wei at first, but eventually warms up to him after he offers to help her with her own cases and proves he's not like all of Pendrew's other undercovers; after cooperation on several cases she gives him a heads-up when [[spoiler:three Water Street Boys' corpses were found under Aberdeen Bridge]].
* FairCop: A subdued version of it. It's still Kelly Hu's voice and there's similarity.
* ReasonableAuthorityFigure: Her EstablishingCharacterMoment is giving a heartfelt lecture to an arrested Wei that he shouldn't throw his life away by hanging out with triads and scumbags. Of course, she shortly thereafter finds out he's an undercover cop, but it goes a good way towards demonstrating she's not the "All perps must be PUNISHED!" type of cop.
** [[spoiler:Jackie said he got the same lecture after his arrest but chose to ignore its message. However by the end of the next mission he will sorely wish he hadn't.]]
* WhatTheHellHero: In the Year of the Snake DLC, she's the one who tells Wei that he's to be demoted for the trail of destruction he's laid in his wake.

[[folder: The 18K Triad]]
!!The 18K in general

The fiercest competition the Sun-On-Yee have for control of Hong Kong, now on the offensive thanks to the civil war within the Triad. Not as big as the Sun-On-Yee, they have begun to use sabotage and subterfuge to tip the power balance in their favor. Said to be far more brutal and immoral than the Sun-On-Yee.
* BiggerBad: [[spoiler: Big Smile Lee was only able to get as far as he did because of them]]
* BlandNameProduct: Named after the real life 14K triad.
* EvilerThanThou: Any criminal service the Sun-On-Yee refuse to offer the 18K will gladly do instead. No money is too dirty, no job is too low. While the Sun-On-Yee are [[EvenEvilHasStandards currently in a civil war over whether their prostitution ring/ human trafficking goes against their honor]], the 18K gave up notions like honor a long time ago.
* EvilIsPetty: The word "petty" does even begin to describe them. [[spoiler: They already were going to kill Winston no matter what for his actions against Dogeyes. What day did they choose? His wedding. Just to maximize the amount of friends and family of his they could kill as well.]]
* NebulousEvilOrganisation: Justified. Wei is not a member of 18K, so we see very little of its inner workings. What is made abundantly clear, is that the Sun-On-Yee, as bad as they are, are far better for Hong Kong than the 18K would be.
* NoHonorAmongThieves: They cross lines the Triads traditionally hold to be sacred, like [[spoiler: butchering enemy red poles at their own weddings]], or [[spoiler: hiring serial killers to harvest organs]].

!!Sakinder Sajan Naz, aka "Naz Singh" (Voiced by T.J. Ramini)

An Indian expat, an associate of the 18K and a police informant, he's aware of Wei Shen's role as an undercover cop.
* CryingWolf: He's the first to clue in that Ricky Wong and Vivienne Lu are pursuing a serious relationship, and suggests in his report that this could be exploited to turn Ricky away from the Triad. However another, more reliable CI dismisses this theory and states that Ricky and Vivienne's relationship is, at best, based around casual sex and not worth looking into. Noting Naz's consistent unreliability and with all the available evidence supporting the other CI's conclusion, Raymond ultimately drops the lead.
* EvilCounterpart: He is basically in the same position as Wei, except he uses it for his own personal gain.
* HoistByHisOwnPetard: Naz keeps a powerful position in the underworld safe by playing the Triads and Police against one another. It comes to bite him back in the ass when Wei, who has even stronger ties to both himself, comes calling.
* MeaningfulName: His code name with the HKPD is "Scoundrel". Raymond [[LampshadeHanging lampshades]] that, for once, the code name is highly appropriate.
* TheMole: He snitches on the 18K to Inspector Teng, but as his police files show, he's usually more interested in using his status as an informant to protect his own criminal dealings than providing any useful info to the police.
** He'd also (correctly) figured that Wei was undercover. When Naz revealed this, Wei counters, "And I know you're a snitch. [[TakeThat You want to see who your boys kill first]]?"
* NiceToTheWaiter: Averted, big time. His treatment of Jackie is what brings him down.
* SunglassesAtNight

!!Four Finger Wu

A Red Pole of the 18K and one of the first Triad members encountered. Heavily involved in the narcotics trade and infamous both for his efficient brutality and his loose grip on sanity. The Hong Kong police are dedicating much of their efforts towards taking him down.
* AxCrazy: His first appearance has him brutally murdering a young security guard with a meat cleaver.
* EstablishingCharacterMoment: Naz and Wei meet him at the docks, and he is clearly already stoned out of his mind, with bloodshot eyes and a crazed glare. A guard shows up, and in the middle of Naz negotiating with the guard, Wu out of nowhere goes to town on the guys ribcage with a cleaver before the guard can even accept or refuse the bribe.
* EvilCounterpart: to Winston, as the brute force Red Pole for his respective Triad, focused on moving drugs and bashing heads in the waterfront/northpoint areas. Unlike [[NobleDemon Winston]], however, Wu is a total psychopath.
* {{Gonk}}: Is always sweaty, wears filthy clothing, and has greasy skin, disheveled hair, multiple chins and bloodshot eyes. The guy is a regular Adonis.
* KickTheDog: Every time he appears.
* SmallRoleBigImpact: Only appears physically once, but many of the police missions deal with putting a stop to his various schemes, and he is mentioned in many other missions (for example, one of Rolands debtors was using the money to buy drugs from Wu). He seems to have specifically targeted the Water Street Boys.
* StupidEvil: Can no longer show his face in public since he was caught murdering said security guard by a clearly visible security camera.
* WeaponOfChoice: Like Winston, a cleaver.

!! Doctor Tsang

A doctor affiliated with the 18K. [[spoiler: Also the serial killer that has been prowling North Point, as part of the 18K's organ harvesting schemes.]]
* BackAlleyDoctor: Patches up the wounds 18K members receive.
* MadDoctor: As someone willing to work with the 18K, this goes without saying.
* WalkingSpoiler: [[spoiler: Is the titular SerialKiller in the "Serial Killer" undercover cases.]]

[[folder: Other]]

!!Amanda Cartwright (Voiced by Creator/EmmaStone)

An American tourist who Wei encounters outside of his apartment. She's exploring Hong Kong as part of a desire to find herself and Wei offers her directions.
* ActionGirl: Implied she wants to be one.
* AllThereInTheManual: Why does she disappear? Turns out, she tends to be the type to have one-night stands.
* ReallyGetsAround: Her police report reveals her GenderInverted YellowFever.
* ShoutOut: Her last name may or may not be a reference to Creator/JamesHong's character's mispronunciation of George Costanza's last name in the ''Series/{{Seinfeld}}'' episode ''The Chinese Restaurant''.
* WhatHappenedToTheMouse: Due to her VA and high profile, everyone playing generally assumed she'd play a big role. After a single story mission, and her photograph quest, she vanishes completely.

!!Tiffany Kim (Voiced by Yunjin Kim)

A Karaoke hostess who works at Club Bam Bam.
* {{Hypocrite}}: Yells at Wei for cheating on her when he confronts her but her police file makes it clear that she's been juggling multiple relationships with men ([[WhatAnIdiot several of them from Triads]]) before she met Wei. Also their relationship [[GameplayAndStorySegregation was really just one date and sex]].
* ReallyGetsAround: According to her police files, she juggles multiple relationships with different triad gangsters... though that arguably comes with the job.
* WhatTheHellPlayer: If Wei cheats on her with Not Ping, she calls Wei out on the double standard (that Wei might consider her to be cheating while he's got another woman on the side) and leaves him.
** Subverted by the revelation she was cheating on Wei (and other guys with him) well before this.

!!"Not-Ping" (Voiced by Celina Jade)

Owner of an electronics store, she hacks into security cameras for fun.
* AscendedExtra: Appears as Wei Shen's girlfriend in Nightmare on Night Point. Before promptly getting kidnapped.
* ExactlyWhatItSaysOnTheTin: Her name is not Ping, despite being the only one working in Ping's Electronics.
* KnownOnlyByTheirNickname: To the point that Wei simply has her listed as Not-Ping in his phone. She never bothers to give her actual name to him.
* PunnyName: Ping being a measurement of a network connection.
* SecretKeeper: Wei meets her on police work and depending on how much of Nightmare in North Point is canon she should also know he's with the Sun On Yee.
* WhatTheHellPlayer: Just like Tiffany, if Wei dates her and Not Ping, she leaves a message that she knows about Tiffany and is really angry at Wei... And then [[MasterOfTheMixedMessage proceeds to ask him to call her]].

!!Mrs. Chu (Voiced by Irene Tsu)

The mother of gangster Winston Chu, she encouraged him to become a Triad gangster in hopes of him making something of himself.
* ItsAllMyFault: She blames herself for encouraging Winston to join the Triads [[spoiler: after his death as a result of being a gangster]].
* JerkWithAHeartOfGold: According to Peggy, she once chewed out Winston for neglecting his fiancée even if it was for Triad's business.
* KnifeNut: That cleaver of hers isn't just for kitchen-work.
* MamaBear: [[spoiler:The men responsible for Winston's death find this out the hard way]].
* NeverMessWithGranny:
** When a group of [[spoiler: Big Smile Lee's]] goons attack the Golden Koi looking for Wei, one holds her at gunpoint. When he turns his back on her as Wei comes in, she almost takes the guy's arm off at the shoulder with her cleaver.
** After [[spoiler: Winston gets blasted to Swiss cheese at his wedding]] she interrogates [[spoiler:Johnny Ratface and then chops up his body into soup meat, which she later fed to his boss, Dogeyes.]]
* TranquilFury: When dealing with the people responsible for [[spoiler:Winston's death]] she never even raises her voice.

!!Peggy Li (Voiced by Lindsay Price)

Winston's kept fiance, she is enthusiastic about her husband-to-be's job as a gangster and eager to welcome Wei into the family.
* BloodSplatteredWeddingDress:[[spoiler: Big time.]]
* CoolBigSis: She tries to be this to Wei, even wanting to set him up with a friend of hers.
* CruelAndUnusualDeath: [[spoiler: Meets the same fate as Winston...on her ''wedding day'']].
* MafiaPrincess: While not as high class as Vivenne Lu, she's actually closer to it as the kept fiance of a Red Pole.
* TogetherInDeath: [[spoiler: She and Winston both died together at their wedding.]]
* TooGoodForThisSinfulEarth: She's Winston's MoralityChain, and one of the few truly positive characters in the game. She values family above all else and is very supportive of her husband and Wei despite their gangster ways. [[spoiler: She dies just one mission later after she's been introduced, horribly gunned down at her own wedding along with her husband.]]
* NeighbourhoodFriendlyGangsters: Seems to believe the Sun on Yee is this or at least the Water Boy Gang.
* WeHardlyKnewYe: [[spoiler:Only has a major presence in one mission...before dying horribly]]

!!Vivienne Lu (Voiced by Creator/LucyLiu)

A famous pop musician who owes her success to the Triads, Vivienne Lu is secretly dating Ricky Wong, the triad liaison to her management.
* TheDanza: Of sorts. Her last name is very similar to her voice actress'.
* MafiaPrincess: Subverted to a degree; Vivienne doesn't work with the Sun On Yee, in as much as they finance her career as a singer/actress and she's dating Ricky Wong, the Sun On Yee liaison to Wo.
* RapeAsBackstory: [[spoiler:She's been used as a reward for Sun On Yee by her boss several times -- in fact, that's how she and Ricky got together! She obviously doesn't like it and has been threatened with being forced into pornography otherwise and according to her, Wei is the first man to say that she doesn't have to sleep with him.]]
* RichBitch: Seemingly a vapid girl who is willfully in denial about her boyfriend's gangster ties. [[spoiler: It turns out she is much more aware than she lets on, considering how they got together.]]

!!Sandra (Voiced by Steph Song)

The speed obsessed debutante daughter of a rich Hong Kong businessman. She is best friends with Vivienne.
* CoversAlwaysLie: Has a spot on the cover implying a bigger place in the game than two dates and by her placement that she is part of the Sun On Yee.
* MafiaPrincess: Zigzagged. Sandra socializes with Vivienne, who has direct ties to the Sun On Yee, but we aren't told whether Sandra actually works for the triads or involved with their operations.
** Given she says she's always wanted to date a gangster, it's highly unlikely she's anything other than just a rich friend of Vivienne.
** Her second date with Wei ends when she gets a call from "daddy" and Wei ends up dropping her off near "Two Chin" Tsao's mansion.
* TheTease: She tries this with Wei. He manages to convince her otherwise.
* UglyGuysHotDaughter: Possibly.
* WhateverHappenedToTheMouse: Like Amanda, she vanishes from the game in every fashion once her dating missions are completed.


Wei's initial contact in the illegal racing ring.
* GracefulLoser: No matter how much shit he talks before (and during) a race, he plays clean, and when he loses he doesn't through a tantrum, unlike Hotshot.
* SpiritedCompetitor: He's interested in racing. He doesn't want to win through cheating.

!!Hotshot (Voiced by Johnson Phan)

An illegal underground racing driver infamous not only for his smug attitude, but for rumors of cheating and manslaughter.
* CheatersNeverProsper: Starts his race with Wei by jumping the gun on the starting countdown. Said race also has a police ambush waiting for him at the end.
* GameplayAndStoryIntegration: Hotshot is nail bitingly frustrating to tail because, as befitting his personality, he blatantly disobeys traffic laws, ignoring stoplights and driving on the shoulder to get around those who don't, and sometimes even gets into fender benders at intersections. In order to stay even remotely near him, you have to break laws as well, which obviously raises your suspicion meter.
* HoistByHisOwnPetard: Became "The Best Racer in Hong Kong" by murdering all his competitors by ramming them off the road. Wei leads him right into a police ambush, then rams his car until it stops working, leading to his arrest.
* {{Hypocrite}}: Frequently uses unfair and downright dangerous moves in his races, but gets in a hiss fit when others do it ''to him''.
* InformedAttribute: His racing prowess, since he murders anyone who dares challenge him and the one time Wei does race him he needs to cheat to stay ahead.
* JerkAss: Made clear from his first appearance.
* SmallNameBigEgo: He certainly ''thinks'' he's hot shit. Simply suggesting otherwise by, y'know, ''actually challenging him to a race'' is sacrilege in his mind.
* SmugSnake: During his race with Wei, he makes several comments about his skill.
-->'''Wei:''' You gotta to cheat to win?\\
'''Hotshot:''' It's not cheating if you win!

!!Sifu Kwok (Voiced by James Lew)
->''"I have given you powerful tools. If they are not used well, surely I bear part of the responsibility."''

Wei Shen's former Kung Fu instructor. An older man with a strong sense of morality, he remembers when martial arts were as much about controlling the mind as controlling the body. The youth of Hong Kong disappoint him heavily, but he continues to teach them nonetheless.
* BadassMustache
* BigGood: As the only authority figure who Wei both respects and actually listens to, he is one of the few things keeping Wei from going over the deep end.
* CollectionSidequest: His collection of Jade Statues was stolen long ago and he'll teach Wei a new combat move for each one he gets back.
* DrillSergeantNasty: While a strict-but-fair father figure most of the time the insults he throws at underperforming students slide into this.
--> NO! I said 'Strong like bear', not 'Limp like noodle'!
--> Your ancestors called! They want to disown you!
* OlderThanTheyLook: In spite of being old enough to have taught Wei, he is still powerfully built with no sign of the "sensei's paunch" and has no grey whatsoever in his hair.
* OldMaster: Younger than normally depicted, perhaps in his fifties. He acts the part to Wei, challenging him with probing questions and teaching him new techniques.
* OOCIsSeriousBusiness: The return of his statues is rewarded with a new technique and a snippet of dialogue concerning mortality, ethics and the general state of the world. When returning the last statue and preparing to learn Dim Mak, all Wei gets is "Pay attention, because this technique is dangerous, and if you abuse it, I'll kick your ass."
* ScrewPolitenessImASenior: His exact age is unknown, but he's been teaching a long time, and he's done mincing words when students disappoint him.
* YouFightLikeACow: [[http://www.youtube.com/watch?v=_fFruTkJOGs He constantly throws insults around during training sessions]].
** In a Subversion...it's mainly to everyone BUT Wei, and for the good reason that they are getting their ASSES kicked.
* WhenIWasYourAge: Is heavily disappointed at how old systems of honor and respect are breaking down in the modern age, and that much of the youth of Hong Kong only want to learn martial arts for the sake of joining triads. Instead of portraying this as a RamblingOldManMonologue, the game makes it clear he's more or less entirely correct.

!!Mimi Shen

Wei Shen's deceased older sister, she was both a drug addict and a prostitute.
* PosthumousCharacter: She OD'd long ago, which forms the basis of Wei's hatred of the triads.
* RapeAsBackstory: According to her Social Services file, she'd been raped so many times she didn't bother to count.
* StockholmSyndrome: Possibly her relationship with Dogeyes. [[spoiler:She even gets back together with him in the afterlife. [[UnreliableNarrator At least according to Dogeyes]].]]