Protagonist
The Freelancer
"Please, I'm a professional."
—Freelancer
The main character of Entry Point, a professional criminal capable of carrying out various dirty tasks by Halcyon, and later, Phoenix.
- Ambiguously Gay: It's heavily implied they had some feelings for Rose regardless of gender, especially since her death was the final straw that led to them defecting from Halcyon for good.
- Ambiguous Gender: They have no canonical gender.
- Animal Theme Naming: The nickname the FBI gives them is Finch, a passerine bird with short lifespans, referencing the lesson the Freelancer learns from Harvey in the Freelance Heists.
- Anti-Hero: While a criminal and very capable of performing morally questionable actions, it doesn't change the fact that they are essential to the story, and are capable of performing pacifist runs.
- Badass Crew: Used to work with other freelancers in their past, and can still apply for this trope if taking on missions with multiple Freelancers.
- Character Customization: Inevitable when the game offers various ways of customizing The Freelancer.
- Consummate Professional: Most of the time, they are mostly concerned about accomplishing the job and nothing else.
- Cruel Mercy: Can potentially spare Harvey at the end of Departure, dooming him to life in prison.
- Face Death with Dignity: They were ready to die as their Last Words before the bombs explodes were " Jackdaw. The mission is complete.".
- Genius Bruiser: Aside from being capable of packing one hell of a punch, it's heavily implied that they are intelligent, as they are able to hack through security, and can effectively fool various people with the right disguises.
- The Hero Dies: Fails to escape the bunker's explosion in Black Dusk.
- Karma Houdini: They get no punishment from the authorities, due to their death in the Black Dusk.
- Kick the Dog: Aside from the fact they can kill civilians, Departure has them along with Harvey killing both Jade and Dmitry, after all, is done.
- Made of Iron: With the right perks and armor, they can withstand a massive amount of bullets (except explosives).
- Malevolent Masked Men: Or women. They can potentially wear various masks.
- Master of Disguise: Can wear disguises to fool various guards.
- Never Found the Body: The FBI considers the Freelancer at large but inactive, unaware of their death after the events of Black Dusk. Which is most likely that the Freelancer's body was recovered by Jackdaw.
- Nice Job Breaking It, Hero: If the Freelancer fails to get Rivera to move from the wall in the basement they're breaching from, they will kill her. While going loud before killing her captor results in her dying, this is the one thing that can get them What the Hell, Hero? rightfully by Jackdaw.
- Only Known by Their Nickname: They are only referred to their Code Name, and never their real name. Case File Summary #010416 nicknames them Finch.
- One-Man Army: There's a major reason why Halcyon should not have let them defect to Phoenix: Aside from the fact that they can withstand waves of law enforcement, they are capable of dealing huge casualties to them (including Aegis Units, Shredders, SWAT Van Turrets, Gunships and even a Super-Soldier with a minigun!)
- Only Sane by Comparison: Of all the members of the crew in the Freelance Heists, they do perform some nasty deeds, but the lack of information about their past makes them this compared to Harvey, who is a paranoiac, Jade who has A vendetta against a Cartel, and Dmitry who is dire need of money to support his family. Yes, they are mostly well-adjusted in spite of this.
- Posthumous Character: They have been dead for the entire game development and the entire story, since the Killhouse was their purgatory, technically the second mission added but first the real mission, which was set after Epilogue and possibly during or after Sunset, while all of the missions and cutscenes in the game are all flashbacks and their memories.
Halcyon
In General
...Our organization has interest and operations all over the globe. For someone with your skills, there will be plenty of opportunities.
—Wren
A criminal organization located in Canada, and The Freelancer's initial employer before "Dedication".
- Animal Theme Naming: Named after a genus of Kingfisher birds.
- Gameplay and Story Integration: The main reason why they're unable to use radios in "Black Dusk" is because the bunker down there has communication issues.
- Nebulous Evil Organisation: They're capable of performing high-level crimes, such as kidnapping, assassination, and raids.
- Screw This, I'm Outta Here: The remaining survivors of Halcyon who claimed that the organization has met its end after the events of "Black Dusk" defect from the organization, with the rest detained not long after.
- Posthumous Character: They been long disbanded for the entire game, as the game is set in a flashback.
- Villain Decay: The Halcyon Operatives in "The Scientist" are unable to be intimidated, and if they detect that either too many operatives were knocked out or Falcon gets knocked out before the control room guards get pacified, they will sound the alarm to take both Rivera and the Freelancer with them, and in "The SCRS", they're capable of sending a gunship to blast both ETF operatives and Freelancers. At "Black Dusk", the operatives over there are able to be intimidated, unable to use radios if left unattended and even when Halcyon Operatives attack the site when the mission goes loud, they're treated on the same levels as Steel Cove operatives, though this is made up for the fact that they will press a button that will sound the alarm if left unattended.
The Director
"Nobody gets to the top by playing nice; you know that better than anyone else. You've been running this game for years, and you know all the tricks. Pawns fall, but nobody will ever take you down."
—Description of The Kingpin's costume
The leader and founder of Halcyon.
- Animal Theme Naming: His Code Name, Kingfisher, is named after a group of small-medium sized birds. Also counts as a Meaningful Name, as Kingfishers are also identified with a genus of Kingfishers called Halcyon.
- Big Bad: He is the main leader of Halcyon, and after "The Lakehouse", he is shown to be antagonistic towards Phoenix and the Freelancer.
- Face Death with Dignity: He accepts defeat with his Last Words before being executed by Jackdaw being "Well then. Get on with it.".
- Foreshadowing: The description of "The Kingpin's Costume" hints at his assassination of his fellow founders of Halcyon and attempted execution of Jackdaw.
- Given Name Reveal: Case File Summary #010416 reveals his real name to be Mason Wolfe.
- Karmic Death: He is killed by Jackdaw in the epilogue, the same person he used to work with before ordering him to be executed during Operation Ember Shroud. The gun Jackdaw uses is the Raven initially used by Rose before being gifted to the Freelancer, both of whom died due to his actions. He even lampshades it, stating that it's quite a long time coming to him.
- Make It Look Like an Accident: It's heavily implied through the Transcript "Insurance" that he rose through being the sole leader of Halcyon through assassinating his fellow founders and covering it up as accidents.
- Minor Major Character: The Director was one of the founders of Halcyon, and attempted to assassinate Jackdaw, which led to the events of this game.(Save for the Freelance Heists.)That being said, he only in the start and the end of the game.
- Non-Action Big Bad: In spite of being the main leader of Halcyon, the Freelancer isn't shown to encounter him. When Jackdaw breaks into his apartment, he calmly accepts his death by him.
- Posthumous Character: He been dead for the entire game, all the cutscenes he appears in are flashbacks.
- Rogue Agent: Was a member of MI6 before defecting from the organization to form Halcyon.
- Sinister Shades: Wears a pair of black shades.
- We Used to Be Friends: It's noted that at one point, Jackdaw used to be a member of Halcyon, but The Director's attempted execution of him during Operation Ember Shroud led him to defect from the organization. Sunset shows a much younger Jackdaw and Director back when they were both operatives.
- You Have Outlived Your Usefulness: Attempted to execute Jackdaw during Operation Ember Shroud after having him alongside other agents to assassinate the other founders of Halcyon. It doesn't work.
Wren
"Cold. Heartless. Professional. Nobody is going to get in your way when you have a job to do, and nobody will ever doubt your loyalty. You'll make sure of that."
—Description of The Dedicated's Costume
One of Halcyon's best operatives who hides a dark side.
- Animal Theme Naming: His Code Name is named after a group of passerine birds.
- Asshole Victim: His death was slow and painful and well deserved, considering his actions.
- Ax-Crazy: He's shown to have a few screws loose once he is ordered to execute the Freelancer. Retribution also revealed that he once served under Jackdaw, but when ordered to execute him, he does so brutally without remorse, and even before that, he also led the Boston Four, which became notorious for at least 17 homicides.
- The Dragon: His loyalty and status as one of Halcyon's best operatives cement him as this, with the "Halcyon" cutscene even showing him next to The Director.
- Faux Affably Evil: He's capable of putting on a polite facade, while also being ruthless as well.
- Given Name Reveal: Wren's combat dossier reveals his name to be Eric Reed.
- Karmic Death: He is killed by Jackdaw, and considering that he's shown to have a few screws loose when executing him, he definitely deserved it.
- Hate Sink: Aside from attempting to kill Jackdaw, he also did 17 homicides, allegedly betrayed his former allies, and even tried to betray the Freelancer. He would soon get what's coming to him.
- Last of His Kind: The last surviving member of the Boston Four unless you count Harvey if he was spared, until Jackdaw executed him.
- Posthumous Character: He has been dead for the entire game, all the cutscenes Wren appears in, are set in flashbacks.
- A Pupil of Mine Until He Turned to Evil: Well, while all of them were "evil" to an extent, he used to train under Jackdaw until the moment where The Director would order Jackdaw's execution.
- The Sociopath: Is capable of putting a charming facade, only to viciously put that away once ordered to perform his job. As an tongue-in-cheek reference, the code used to access his file is even called "Sociopath"!
- Undying Loyalty: In spite of his unsavory methods, he is absolutely loyal to Halcyon.
Rose (UNMARKED SPOILERS)
"They think today is going to be quiet, but you're going to start a fire. You have to keep things interesting, right? Nobody likes the boring plan, and you'll make that abundantly clear to them."
—Description of The Wildcard's Jacket
The mission coordinator for the Freelancer and the co-founder of Phoenix.
- Posthumous Character: She has been dead for the entire game, all the mission and cutscenes she appears in are flashbacks.
- Sacrificial Lamb: Her death is what led to the Freelancer to defect to Phoenix and join Jackdaw's crusade against Halcyon.
Falcon
"You're the quiet one. Always there, but rarely noticed. Most people only see the uniform, and that's the way you like it. They don't realize they've underestimated you until it's too late".
—Description of The Hunter's Costume
An high ranking operative of Halcyon who first appears as the escape pilot for "The Blacksite", he later serves as the commander of safehouse that holds Rivera in "The Scientist".
- From Camouflage to Criminal: Was a former member of Steel Cove before defecting to Halcyon due to an dispute that ended with the death of an officer.
- Getaway Driver: Or a getaway pilot. He serves as the escape pilot for the mission "The Blacksite".
- The Quiet One: He only ever speaks twice in the game: When he is talking to his second-in-command with his radio, and confirming his killing of Rose.
- Posthumous Character: He has been dead for the entire game, the mission he appears in is a flashback.
- Uncertain Doom: Downplayed; his doom was certain, it's unknown how he was killed; either in a crossfire between TRU, Halcyon and Phoenix in Ontario or knocked out during the extraction of Rivera, then presumably killed afterwards by Phoenix.
Phoenix
In General
"Jackdaw isn't working alone; he's brought a new shadow organization to the game, and this is nothing short of war."
—Mission Briefing for The Financier
A criminal organization composed of former Halcyon members, located in the United States.
- Animal Theme Naming: They are named after The Phoenix, a mystical bird said to be a symbol of death and rebirth. Jackdaw was "reborn" as a criminal through his defection from the CIA and later though to have supposedly died via being betrayal before rising back through the founding of Phoenix, Sparrow was a former US Air Force pilot before resurfacing as a getaway pilot for Phoenix.
- Breaking the Fellowship: Phoenix is disbanded following Black Dusk, leaving most members to carry on with their lives using Halycon's stolen accounts.
- Elite Mooks: Compared to the other guards, they're unique that in "The Lakehouse", holdups do not work on them (aside from the camera operator), and always have a radio on unless the commander is taken out.
- Hazy-Feel Turn: Most of the members were that of former Halcyon members due to Mistreatment-Induced Betrayal or through other methods.
- Karma Houdini: Most to all of the members are implied to have escaped punishment from authorities after the events of Entry Point. This also includes the late Freelancer, Sparrow and Jackdaw.
- Screw This, I'm Outta Here: After the alarm is raised in The Lakehouse, most of the guards will immediately disappear if they aren't shooting at the Freelancer, and for absolutely good reason: Steel Cove is beginning an assault, and they're bringing in a Gunship as well!
Jackdaw (UNMARKED SPOILERS)
"They'll try to knock you out, break your spirit. But you'll hit back, harder than they ever expected. You've got plans within plans, and nobody is going to keep you down. Let's get to work."
—Description of The Survivor's costume
The leader and founder of Phoenix.
- Animal Theme Naming: His Code Name is named after a group of crows.
- Affably Evil: Earlier he wasn't nice to the Freelancer, but later he would start to act nice to him.
- Berserk Button: Failure of objectives can really set him off, unlike Rose.
- Big Damn Heroes: Saves the Freelancer from being executed by Wren through shooting Wren.
- Choice of Two Weapons: The Black Dawn prologue shows him using both a Thumper and a S97.
- Disc-One Final Boss: He's initially set up as the Big Bad. He's not, and in fact, saves the Freelancer from certain death.
- Eyepatch of Power: Has an eyepatch on his right eye. The Freelancer can obtain this by completing the Halloween Hitlist 2020 mission, fittingly named Jackdaw's Eyepatch.
- Given Name Reveal: Jackdaw's combat dossier reveals his name to be Jack Miles.
- Karma Houdini: Just like the Freelancer, he gets no punishment for what he did after the events of Entry Point. But this came at a price, which would leave him forever scarred by the death the Freelancer for the rest of his life.
- Mission Control: While he did want Halycon to be gone and win the war, this came at a large price, after the events of Entry Point the losses of Rose and The Freelancer deeply affected him, and was especially forever scarred by the Freelancer's death.
- Rogue Agent: Used to be a CIA agent before being recruited to Halcyon.
- Shell-Shocked Veteran: The events of Entry Point, along with deaths of the Freelancer and Rose, had been harsh on him and he isn't able to move on since the deaths of the two had affected his mind, leaving him depressed and forever scarred, which is all discussed during Sunset.
- Walking Spoiler: It's very hard to talk about him without describing his appearance in Payoff, and it only gets harder to talk about him without revealing that he was essential towards the Freelancer's defection towards Phoenix.
- We Used to Be Friends: It's noted that at one point, he used to be a member of Halcyon, but The Director's attempted execution of him during Operation Ember Shroud led him to defect from the organization. Sunset shows a much younger Jackdaw and Director back when they were both operatives.
Sparrow
"Some days, it's just you against the world - and you're going to show the world who's boss. It takes a special kind of crazy to accept the risks you do, but that's what it takes."
—Description of The Fearless' costume
The getaway pilot for most of Phoenix's operations.
- Ace Pilot: She's described as a skilled pilot who takes many risks. It helps that she was a former member of the US Air Force.
- A Day in the Limelight: April Fools 2020 focused on her specifically, with all of the NPCs having their hair dyed to resemble her hair color during missions, and her providing commentary for all of the cutscenes.
- Affably Evil: She's surprisingly pleasant for a criminal.
- Ambiguous Situation: Exactly what led to her deserting the US Air Force and joining Phoenix? It's never explained in-game, to the point where not even files relating to The Lock have any information on how she deserted.
- Animal Theme Naming: Her Code Name is named after a group of Passeridae.
- Break the Cutie: She did not take Rose's death well if her commentating on "Retribution" is of any indication. Given that Rose was also a member of Phoenix, it's heavily implied that it was very personal for her.
- Earn Your Happy Ending: The only member of Phoenix who downright gets a happy ending; not only is she revealed to be happily married to someone but also inherits part of Phoenix's offshore accounts as well.
- Karma Houdini: She gets no punishment for her crimes after the events of Entry Point.
- From Camouflage to Criminal: Her dossier in The Lock revealed that she was a former US Air Force pilot before joining Phoenix.
- Getaway Driver: Or a getaway pilot. She's responsible for helping in extraction for most of the Freelancer's operations when they go loud (with the exception of The Scientist).
- #HashtagForLaughs: During April Fools 2020, when she notes her lack of appearance in the "Halcyon" cutscene, she makes up a hashtag titled "#SparrowOrRiot".
- Hypocritical Humor: During April Fools 2020, when commentating on the "Halcyon" cutscene, she wonders what kind of person would name themselves after a bird after seeing Wren's name. She's named after a bird.
Ryan Ross
"You've got the wealth, you've got the helicopter, and you've got the enemies. Sure, you're being hunted by a shadow organization, but at the very least, you're still living in style."
—Description of The Capitalist's costume
The titular financier, whom Halcyon seeks to either capture or eliminate and stop Phoenix from getting funds for the Shadow War.
- Defiant to the End: Should his panic room door be breached in loud, he'll attempt to shoot the Freelancers with his Raven even when cornered.
- He Knows Too Much: His extreme knowledge on Phoenix’s operations is what made him a target to Halcyon.
- Properly Paranoid: His apartment is littered with security cameras that don't require an operator, has bodyguards that have a frequent radio check in who'll raise the alarm after one minute should four bodyguards be knocked out or killed. Ryan also has a personal bodyguard that will follow him around in Legend, and the guard counts towards the knockout limit but Ryan doesn't notice them gone.
- Posthumous Character: The missions and cutscenes are all set in flashbacks, implying he was dead for the entire time.
- Sharp-Dressed Man: Is dressed up in The Capitalist's costume.
- Uncertain Doom: The mission description for "The Cache" mentions how Phoenix lost all contact with him after the events of "The Financier", and the Freelancer is assigned to transfer his holdings to a more secure Phoenix accounts. Ryan is confirmed dead after the events of The Financier if left alive, this is confirmed by the community as he was assassinated by a Halcyon Operative.
Rivera
Placeholder
- Posthumous Character: This is her fate if she has been killed.
- What Happened to the Mouse?: Rivera's fate is left unknown after the events of "The Scientist". If Rivera is left alive, She mostly helps Phoenix with what they need. Furthermore, her dossier in The Lock lists her status as MIA, meaning that while it's possible that she survived, her getting killed is also a possibility.
Law Enforcement
CSIS
"Thanks to the intel we got in London, we've got a specific target in mind - a classified northern bunker Halcyon is using for research. We've got what we need to fake your credentials and get you inside, but we'll need schematics of the facility to properly plan a strike."
— Pre-mission briefing of The SCRS
The SCRS or more properly known as 'Le Service Canadien du Reseignment do Sécurité' in French (translated to 'The Canadian Security and Intelligence Service' in English) is a minor faction that is allied with Halcyon.
Two of their agents, Hemlock and Nightshade, appear as one of the unique guards.
- Cool Shades: Nightshade wears a pair of sunglasses all the time, just like Wren.
- Floral Theme Naming: Hemlock and Nightshade's Code Names are named after poisonous plants.
- Only Known by Their Nickname: Hemlock and Nightshade's real name is unknown.
- Posthumous Character: This is Hemlock and Nightshade's fate if they have been killed.
- Stocking Filler: One notable trait about Nightshade is that she is the only character in the game to wear fishnets, though it's covered by her jeans.
- What Happened to the Mouse?; Their fate is left unknown after the events of "The SCRS", but it's likely they'll undergo an scandal if their ties to Halcyon were exposed to public. If Agents Hemlock and Nighshade were left alive, they most likely end up being fired for not taking action against The Freelancer at worst.
- You Have Outlived Your Usefulness: Implied to be on the receiving end of this: Should the mission in their debut go loud when three servers are hacked, Halcyon will send in a Gunship to blast both Phoenix and SCRS operatives.
Other Freelancers
Harvey (UNMARKED SPOILERS)
Harvey was a character who appeared during the stand-alone story of "The Freelance Heists" working as a Mission Coordinator.
- Backstab Backfire: His attempt to kill the Freelancer ended up getting him injured. Whether he dies or not is dependent on the player.
- Con Man: Teamed up with the Freelancer to double cross Jade and Dmitry in order to get all the gold for themselves, then he attempted to betray the Freelancer. It doesn't go well.
- Last of His Kind: Should he be spared at "Departure", not only is he the sole surviving member of "The Freelance Heists", but also technically the sole survivor of the Boston Four, since he technically was part of their group, and all four members, including Wren were killed.
- Posthumous Character: This is his fate if he has been killed.
- You Have Outlived Your Usefulness: After stealing 20 million, Harvey and the Freelancer killed Jade and Dmitry, then Harvey tried to kill the Freelancer.
Jade
Jade was a character who appeared during the stand-alone story of "The Freelance Heists" working as a Sniper and Mission Coordinator.—-
- Posthumous Character: She was dead for the entire game.
Dmitry
Dmitry was a character who appeared during the stand-alone story of "The Freelance Heists" working a Getaway Pilot and Mission Coordinator.—-
- Mother Russia Makes You Strong: Subverted. Despite being from Russia and looking tough on the outside, Dmitry is a pacifist and hates all kinda of violence, only getting involved in crime to support his family.
- Posthumous Character: He was dead for the entire game.
