Warning: Spoiler tropes ahead.
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Jesse (Main Character)
A journalist writing for the New York Herald who bears witness to the events of Birchport since the disappearance of their friend Kate O'Malley during her wedding day
- Amateur Sleuth: Becomes one after learning that for this case, the Police are Useless.
- Bi the Way: Jesse can romance Grant, Flynn and/or Naomi as well as flirt with the Frat Boy in Chapter 6 for information (with additional special dialogue if Jesse is male) as either gender.
- As of the last chapter, Kate is also a love interest, with the main character always having been in love with her if you pick this option.
- Brains and Brawn: When teaming up with Flynn, the latter is the muscles to Jesse's deductive mind.
- Buffy Speak: Jesse comments that the forest looks "woodsy".
- Character Customization: The player can choose to play Jesse as a male or female character, among the other appearance details.
- Deadpan Snarker: Rarely goes more than a few sentences without making a sarcastic remark. The player can emphasize this trait even further by choosing to defy the elites in Birchport and in Jesse's interactions with Flynn and Scarlett.
- Determinator: Will NOT give up investigating Kate's disappearance despite repeated threats from Pierce Sterling and Tommy Walsh.
- Gamer Chick: A female Jesse can be one of these in the premium scene in Chapter 2 if they confess this fact to Naomi.
- Hello, [Insert Name Here]: Jesse is the default name.
- I Choose to Stay: In the last chapter, Jesse can choose to stay in Birchport with a love interest by paying diamonds.
- I Know Karate: A Premium scene in Chapter 2 can have Jesse reveal this.
- Intrepid Reporter: Before the story begins, Jesse is a reporter for the New York Herald. The intrepid part really kicks in at Chapter 2.
- I "Uh" You, Too: In Chapter 15, either Flynn, Grant, or Naomi (depending on who you have been most intimate with) will nearly confess their true feelings. Jesse shuts them up with a kiss and tells them to tell Jesse when they return.
- Long-Haired Pretty Boy: A male Jesse with the Fabi-Oh hairstyle is this.
- Platonic Life-Partners: Even as a male, Jesse is only identified as Kate's roommate, their relationship never stated to be more than best friends. Subverted if Jesse chooses to be more than best friends and stays with Kate in Birchport at the end.
- Sherlock Scan: The game encourages the player to pay attention to the surroundings and the dialogue. In a Premium choice in Chapter 2, Jesse deduces correctly that Kate couldn't have fled her own wedding without her wallet or drivers license.
As a whole
- Big, Screwed-Up Family: Beside Tanner, all of the other Sterlings as well as their close associates are crazy: Bryce is a drunk, jealous asshole, Pierce and Margaret are drug dealers, Nikolai is a drug bouncer hopelessly in love with Margaret (to the point of being willing to kill for her), and Taylor Acosta/Jeff Duffy is a murderous Green-Eyed Monster mastermind.
- Foil: To their rivals the Emersons. The Sterlings are an Old Money family of European descent who have controlled Birchport's economy since Magnus established his shipping company in the town. The Emersons are an African-American family who made their fortune since Grant's grandfather worked as a lawyer. Even their respective houses reflect this; the Sterling manor has traditional architecture while the Emerson mansion has modern architecture.
- I Own This Town: They have massive influence over Birchport due to their control of the area's economic activity.
- Old Money: The Sterlings are a family of shipowners who have lived in Birchport since it was first settled and pratically own the town.
- Rich Bitch: Seems to be the general consensus of everyone who interacts with them.
- Slave to PR: They are deeply unpleasant and racist towards the Emersons, but keep this attitude in check so as not to harm their reputation. This is demonstrated most clearly in their reaction to Kate O'Malley's disappearance and the fact that they still host a Fourth of July party after Tanner's murder.
- Walking Spoiler: Especially Pierce and Margaret, but the entire family is subject to this given what happens to them in the story.
Tanner's father and the patriarch of the Sterling family
- Character Death: At the end of Chapter 15, you can choose to let both him and Duffy die, or you can choose to save one of them. Even if you save him, the bonus epilogue reveals he dies six months later in prison.
- Even Evil Has Loved Ones: He flies into a rage at Duffy for murdering his sons.
- Happy Marriage Charade: Margaret and Pierce no longer love each other after Pierce's affair with Alanis, but they keep up appearances as a married couple since each of them know the other's past as drug dealers.
- Jerk with a Heart of Jerk: Once he learns that Duffy is his illegitimate son, he tries to convince him that all was Margaret's doing and all he wants is to reconnect with him, the son of the only woman he has ever loved. Once they get outside, Pierce signals Naomi to shoot at Duffy, admitting out loud that he lied and Duffy will never be more than a bastard who killed his real sons.
- Laser-Guided Karma: He either dies on the ship, or he gets arrested for all the crimes he commited.
- The Patriarch: The main leader of the Sterling family.
- Pet the Dog: If he was rescued in Chapter 15, he will change his will to leave all of his assets to Kate despite his dislike of her.
- Sole Survivor: Determinant. He is this for the entire Sterling bloodline, along with Tanner and Kate's unborn child, if Jesse chooses to save him in Chapter 15.
- Your Cheating Heart: He slept with his secretary Alanis Acosta and fathered a child named Taylor (whose name was later changed to Jeff Duffy) with her.
Margaret Sterling née Van Dyke
Tanner's mother and the matriarch of the Sterling family
- Alas, Poor Villain: As she dies, she looks at Kate with "something close to love" and begs her to take care of her (Kate's) baby (Margaret's grandchild).
- Asshole Victim: She had Nikolai murder her husband's mistress and intended for him to murder her child (granted, he didn't follow through with that one unbeknownst to her, but she still ordered it). And she was also complicit in the large amounts of crimes the Sterlings committed after turning their shipping empire into a drug empire. Her death at Duffy's hands is karmic.
- Happy Marriage Charade: Margaret and Pierce no longer love each other after Pierce's affair with Alanis, but they keep up appearances as a married couple since each of them know the other's past as drug dealers.
- I Coulda Been a Contender!: Chapter 3 reveals she used to be a champion tennis player who could have gone pro, but married Pierce instead.
- The One That Got Away: Turns out Nikolai was in love with her. She never returned his affections physically, but used this as an advantage to manipulate him into murdering Alanis.
- Pet the Dog: The reason she acted so hostile towards Kate is because she knew that marrying a Sterling is hell and Kate imagining a "Prince Charming" was just setting herself up for disappointment.
- Sacrificial Lion: Was killed off in Chapter 14 as part of The Reveal of Duffy being the mastermind.
- Silk Hiding Steel: She is shown to handle a gun very well when she discovers Jesse and Flynn snooping around in her bedroom, and would likely have killed them had Naomi not intervened.
- Thicker Than Water: Despite being hostile to Kate, as soon as she learned that Kate was pregnant with Tanner's child, she pleaded with her dying breath to keep her grandchild safe.
- Wicked Stepmother: Invoked by Jeff Duffy, whose mother was killed by Nikolai on her orders.Duffy: I wasn't destined to be this loser. I was cheated out of my birthright. By you, Margaret. WHEN YOU KILLED MY MOTHER! (shoots Margaret in the stomach) Sorry, Margaret. The evil stepmother always dies.
- Woman Scorned: Her jealousy of Pierce's affair with Alanis made her order Nikolai to commit arson on the latter's house.
Pierce and Margaret's oldest son, and the man Kate was to marry prior to her disappearance
- Bitch in Sheep's Clothing: At first, he seems like a nice and polite guy. When he finds out Kate has been drinking, he is more worried about himself looking bad if his bride arrived hungover at the wedding, adopting a more patronizing tone toward her.
- Character Shilling: The player is given the option to comment on how hot Tanner looks, despite having an average character design. Besides his brief characterization and the flaws revealed during the case, it's a wonder why Kate and Scarlett are so smitten with him.
- Character Death / Slashed Throat: Jesse and Flynn find him dead in the Ulysses with his throat cut ear to ear in the fourth chapter.
- Hypocrite: In a sense. Tanner becomes angry at Kate for risking embarrassment by getting drunk the night before their wedding and angrily drags her away. Tanner getting angry at Kate for disloyalty is rather hypocritical given how he was cheating on her with her own maid of honor.
- It's All About Me: After Kate's disappearance, Tanner appeared more upset about how Kate failed him and ruined his public image than he is about Kate's safety and whereabouts.
- Posthumous Character: Tanner is killed very early on in the book and only appears in 2 chapters.
- Red Oni, Blue Oni: The calm and rational blue to Bryce's red.
- Sacrificial Lion: The first of the major characters to be killed off to show how deadly the killer is, as well as the Anyone Can Die nature of the book.
- White Sheep: Despite his flaws, Tanner is actually the nicest and least evil among the Sterlings. He is not known to be involved in his parent's drug shipping empire, and he is not shown to be a perverted Jerkass like Bryce. He is willing to marry someone from a poorer background than him and acts genuinely hurt and confused when she disappears (albeit that was largely due to shame at how it embarrassed him). In addition, he never acts elitist toward Kate and Jesse, and has been long-time friends with Grant despite the feud between their respective families. Despite being the "white sheep" of his family, Tanner is still far from spotless; he was having an affair with Kate's own maid of honor, Scarlett, and in the first chapter he is shown to get physical with Kate by dragging her away from Jesse by the arm.
- Your Cheating Heart: In Chapter 4, Kate's diary reveals that she suspected Tanner of cheating on her. This is confirmed in the next chapter when it's revealed that he had an affair with Scarlett Emerson.
Tanner's alcoholic younger brother
- Asshole Victim: While Bryce's known crimes are nowhere near as serious as his parents (and he probably didn't deserve to die), Bryce is still a complete asshole. He ruined Flynn's life, harassed Kate despite having a crush on her, stole her underwear and secretly installed a camera in her bedroom, and it is stated in the 9th chapter that he is "handsy" with the waitresses.
- The Alcoholic: He's quite drunk at the rehearsal dinner in Chapter 1. In fact, he's at least somewhat intoxicated in almost every scene he appears in.
- Big Little Brother: He looks older and bulkier than Tanner, who is the eldest.
- Black Sheep: During the Fourth of July gala in Chapter 9, he complains about his status as this in front of his family and the guests.
- Character Death: Hes killed off in Chapter 9 when the fireworks behind him all explode at once!
- Never Found the Body: Initially, there were no traces of Bryce's body and it is explicitly stated that it wasn't found. Because of this, many in the fanbase believed that he was alive and would return, but this turns out to be a Subverted Trope - Naomi confirms in the final chapter that Bryce indeed died from the fireworks.
- Fat Bastard: He is openly disrespectful toward Kate, and frequently brings up the fact that she is poor compared to his family.
- Hypocrite: He spends most of his time humiliating Kate in front of everyone, openly calling her a whore and a Gold Digger. In Chapter 13, if Jesse and Flynn search his room, they discover that Bryce was really obsessed with Kate, finding one of her bras in his closet, and his Internet history reveals that he bought the spy camera in Kates room.
- "It" Is Dehumanizing: He used the word "it" to describe Kate when talking to Tanner shortly after her disappearance.Bryce: I told you, bro. Go roll around in the trash all you want, but don't bring it home.
- Karma Houdini: According to Flynn in a premium option in Chapter 4, Bryce got away with keying Flynn's car while the latter got sent to jail for stealing his car as payback (with the intention of returning it afterwards). Though years later, he finally got his explosive karma.
- The Pass Word Is Always Swordfish: If Jesse chooses to search Bryces room in a Premium option, they easily access his computer. How? The password is Password.
- Posthumous Character: He is already dead by the time Jesse begins telling their story to Agent Kim.
- Red Herring: Several clues point to him being Kate's kidnapper. He's not, Deputy Duffy is.
- Red Oni, Blue Oni: A very loud red to his brother Tanner's blue.
- Spy Cam / Panty Thief / Stalker with a Crush: He gave Kate a teddy bear with a spy camera in it and stole her underwear. This is blatant Irony that highlights Bryce's atrocious character; despite him deriding Kate mercilessly and subjecting her to cruel poverty shaming, he had a large crush on her.
- Trash of the Titans: When Jesse and Flynn break into the Sterling Manor, they end up in a very nasty looking bedroom with piles of dirty laundry and a lot of bottles. They immediately guess its Bryce's room.
Jeff Duffy/Taylor Acosta
- See Law Enforcement folder
Jesse's friend in college and the bride of Sterling heir Tanner; her disappearance serves as the catalyst for the events in Birchport.
- All Girls Like Ponies: During her impromptu Bachelorette party, Kate wants to order a special cocktail inspired by unicorns, because she can literally taste the sparkles.
- All the Other Reindeer: Because of the social status difference between Tanner and her, townspeople from all the social spectrum think of her as a Gold Digger, not feeling any kind of concern about her disappearance.
- Babies Ever After: At the end of the story, she has Tanner's daughter named Rachel.
- Beauty Is Never Tarnished: Averted. When Jessie and Naomi find her in the cabin's basement, she has her make up smudged, has visible bruises, and her nails are all broken and bleeding from her attempts to escape.
- Bi the Way: Her Premium scene in Chapter 8 reveals that she has dated women before.
- As well as becoming an official love interest to a player character of either gender in the final chapter.
- Break the Cutie: Despite her perky personality, she carries a lot of baggage from before she even met Jesse. Her father left her and her brother, which is still a sore point for her to talk about. Then her brother is sent to jail before she enrolls at college. After she falls in love and gets engaged to Tanner Sterling, almost everyone in town resents her, giving her a bad reputation around town, and even the Sterlings (including her own fianceé) dismiss and humiliate her on multiple occasions. On top of all of that, she gets kidnapped right before her wedding and her fianceé is murdered. And that's only the beginning. After she gets rescued, Chief Walsh accuses her of murdering Tanner, who she just learns is dead, has to endure a rigged trial against her case (only saved by Jesse finding more evidence to prove her innocence), and later finds out that she's pregnant with her dead fiance's child, which prompts Duffy to kidnap her again to kill her.
- Damsel in Distress: Jesse, Grant, Naomi and Flynn are the only people in Birchport who believe she had been kidnapped before the wedding, while everyone, including her own fianceé, dismiss her disappearance. Finding her in the cabin confirms that she was in this situation.
- First Girl Wins: The first girl to appear and greet Jesse at the beginning. Potentially, the love interest who Jesse chooses to stay with in Birchport at the ending.
- Gold Digger: Because of her lower-middle-class roots (the daughter of a dockworker), her marrying Tanner, the heir to the wealthiest family in town, has caused some to view her as this. Bryce directly accuses her of this out loud at the recital dinner in Chapter 1. It happens again in Chapter 6 when two of her former coworkers at the bar call her one as well.
- Hard-Drinking Party Girl: According to Jesse, she used to be this. She gets very excited when Grant and Jesse suggest throwing her a Bachelorette Party, commenting on a cocktail that looks and tastes like a unicorn.
- Runaway Bride: Chapter 1 ends with Kate having disappeared from her own wedding. It's eventually subverted when it's revealed that she was drugged and kidnapped.
- Ship Tease: Has a few moments with Jesse before her disappearance and after she is found, especially in the Premium scene.
- In the final chapter, she becomes an official love interest for Jesse, which confirms the Ship Tease as intentional.
- Sibling Yin-Yang: According to Jesse, she is sweet and bubbly, while Flynn is tough and aloof.
- Uptown Girl: Deconstructed. As a dockworker's daughter marrying into one of the richest families in town, some people believe her to be a Gold Digger.
Kate's protective older brother, who later tags along your character for the investigation
- Bi the Way: He can be a Love Interest regardless of Jesse's gender. If Male!Jesse wears a suit to the wedding, he openly comments how hot Jesse looks.
- Big Brother Instinct: If Jesse tells off Bryce at the recital dinner for calling Kate a gold digger, Flynn tells Jesse he's glad they did it or he'd have beaten Bryce to a pulp.
- Brains and Brawn: When he teams up with Jesse, he's the muscles to Jesse's deductive mind.
- Chaotic Good: He is the rebel of the group, being an ex-convict, with his preferred method of breaking in for clues, next to Naomi's Neutral Good and Grant's Lawful Good.
- Character Development: The events of the story turn him from an aloof outsider to someone who starts to open up and rely on others, most notably building up a deep friendship with Jesse (and a potential romance), Grant (someone who he would never interact with because of their different social classes) and Naomi (someone he would usually hate given that Birchport's corrupt legal system ruined his life) as well as reconnecting with his sister Kate.
- Cool Uncle: To his niece Rachel, according to the epilogue.
- I "Uh" You, Too: In Chapter 15, Flynn (if Jesse has romanced him) wants to confess his true feelings in case anyone dies. Jesse shuts him up with a kiss and tells him to tell them when they get back.
- Love Interest: He is the second one to be introduced.
- Mundane Solution: If Jesse fails to guess the password to Kate's lockbox, Flynn's solution is to smash it open, taking a chunk of Kate's desk along with it.
- Sugar-and-Ice Personality: He acts aloof, distant and even violently toward everyone in the story who isn't his sister or Jesse (with good reason). Later he adds Naomi and Grant to the list as well because of their efforts to help Kate.
- Sibling Yin-Yang: According to Jesse, Kate is sweet and bubbly, while he is tough and aloof.
- Tattooed Crook: He has tattoos and has been to jail for stealing Bryces car.
- Too Much Information: When he and Jesse search Kate's bedroom, he asks Jesse to not tell him if any weird objects are around. If Jesse opts to joke about Kate having sex toys, he will freak out.
A lawyer attending the wedding of Kate and Tanner
- Bi the Way: He is a potential Love Interest regardless of Jesse's gender.
- Cool Boat: His speedboat is called "Freedom".
- Glory Hound: In Chapter 12, he complains that people like him who work behind the scenes are never recognized for their achievements, and fail sometimes while people like Flynn get to do all the heroic action and receive all the credit, hence their argument over who gets to steer Grant's speedboat.
- Hello, Attorney!: He became a lawyer like his father, though he chose to become a criminal defense attorney rather than going into corporate law like his father hoped he would.
- Lawful Good: He is the lawyer of the group, handling the legal aspect in court, next to Naomi's Neutral Good and Flynn's Chaotic Good.
- Love Interest: The first one Jesse meets at Birchport.
- Non-Idle Rich: He is the eldest son of the second richest family in Birchport, became a Criminal Defense attorney instead of a corporate lawyer, and is notably the only decent person who treats everyone with respect, regardless of their social status.
- Sibling Yin-Yang: He is calm, mature and polite, in contrast to Scarlett, who is vain, aloof and sassy.
- Token Good Teammate: He is the only one of the elites who expresses concern about Kate's well-being and is actively helpful with investigating her disappearance. He is also one of the only characters who isn't elitist towards Jesse or the O'Malleys.
Grant's sister and Kate's maid of honor during her wedding day
- Alpha Bitch: She is the daughter of the second richest family in Birchport and behaves equally as elitist and full of herself as the Sterlings, treating Kate poorly despite being her Maid of Honor.
- Brought to You by the Letter "S": She always wears a necklace with an "S" from her first name. When inspecting Tanner's yacht, a bracelet with "SE" is found, connecting her immediately with Tanner's murder.
- Deadpan Snarker: She wastes no time making sarcastic remarks about Kate and Tanner's relationship. The very first time she meets Jesse, she wastes no time in insulting Jesse's look.
- Drowning My Sorrows: In Chapter 9 at the Fourth of July Gala, shes at the bar getting drunk.
- The Friend Nobody Likes: Kate has no option but to have her as Maid of Honor because she has no friends in town until Jesse arrives. She spends all of Kate's impromptu Bachelorette Party complaining and throwing insults at Jesse.
- Green-Eyed Monster: She deeply resents Kate because Tanner refused to leave Kate for her.
Scarlett: Don't you ever get tired of being the second richest family in town, Grant? Aren't you looking forward to being the first?
- She also resents her family's position as Birchport's second richest family.
- Hopeless Suitor: She was in love with Tanner since they were kids, but Tanner got together with Kate. Even when Tanner started to cheat on Kate with Scarlett, he never loved her enough to leave Kate. When Tanner gets murdered, Scarlett resents the most that now its too late for her to get Tanner for herself.
- Hypocrite: She calls Kate a "tramp" even though she herself had an affair with Tanner.
- It's All About Me: In Chapter 2, she reveals that just before the ceremony, she saw Kate talking on her cellphone near the woods. Instead of being concerned about Kate's odd behavior, she is more fixated on Kate ignoring her.
- The Mistress: Tanner was cheating on Kate with Scarlett, even while he was engaged. Scarlett wanted Kate to be gone and Tanner to choose her, but he never returned her feelings properly.
- Sassy Black Woman: She definitely has the sass down.
- Sibling Yin-Yang: She is vain, aloof and sassy, in contrast to Grant, who is calm, mature and polite.
- What Happened to the Mouse?: Aside from Hornby mentioning her during Kate's trial and a brief mention in Chapter 16, she disappears from the story after Chapter 9 and is never seen again. She doesn't even have a Where Are They Now moment in the epilogue.
Agent Michael Kim
An FBI agent interrogating Jesse of the events in Birchport since Kate and Tanner's wedding day
- Greek Chorus: Each episode starts with Agent Kim commenting on what Jesse just told him before picking up from the last point.
- Late to the Tragedy: The story starts with him talking to Jesse about how by the end of it, within one month, at least four people ended up dead.
- Not So Stoic: Is shocked when Jesse tells him that Walsh arrested Kate in the hospital room at the start of Chapter 9.
- Reasonable Authority Figure: Compared to most of the other law enforcement officers in the story, he definitely comes across as this. At the end, he decides not to charge Jesse for some of the crimes they committed during the investigation (like breaking and entering), reasoning that Jesse's actions ultimately served the greater good. He even offers Jesse a job with the FBI.
Deputy Naomi Silverhawk
A deputy of the Birchport Police Department who helps Jesse investigate Kate's disappearance
- All Girls Like Ponies: She owns several horses, and often goes horseback riding on her ranch.
- Big Damn Heroes: Showed up to smash Margaret with a vase when the latter held Jesse and Flynn at gunpoint.
- Bi the Way: She can be a Love Interest regardless of Jesse's gender.
- Fair Cop: She is depicted as being very attractive for a police officer. Her popularity skyrocketed when fans got a glimpse of her in civilian clothes.
- Inspector Lestrade: She is the only member of Birchports police department who supports Jesses investigations.
- I "Uh" You, Too: In Chapter 15, Naomi (if Jesse has romanced her) wants to confess her true feelings in case anyone dies. Jesse shuts her up with a kiss and tells her to tell them when they get back.
- Last Girl Wins: The last girl who Jesse sees and potentially becomes romantically involved with. Becomes this if Jesse chooses to stay with her in Birchport.
- Love Interest: She is the third one.
- Neutral Good: Shes the groups law enforcer. As a deputy, her duty is to follow the law, but she is capable of discerning when to take matters into her own hands, next to Grant's Lawful Good and Flynn's Chaotic Good.
- Reasonable Authority Figure: She agrees to help Jesse investigate Kate's disappearance, agreeing that the longer they take to find her might be a matter of life or death for her.
- Token Good Teammate: Of the police force. Which she is eventually fired from.
- Tomboy with a Girly Streak: She tells Jesse that she was an outdoors girl as a kid, and in the Premium scene of Chapter 2, she admits she's fond of romance novels.
- Twofer Token Minority: She's a Native American woman in a job dominated by white men, which puts her at odds with Tommy Walsh and his racism.
- Why Did It Have to Be Snakes?: In Chapter 7, she is shown to be afraid of rats.
- You Are in Command Now: At the end of the story, she becomes the new Chief of Police in Birchport.
Chief Tommy Walsh
The chief of the Birchport Police Department and a close friend of Pierce Sterling
- Asshole Victim: He was killed by Jeff Duffy after years of bullying him, and even after the revelation of Duffy's real identity, it's still hard to feel sorry for Walsh. Not to mention, although it is unknown if Duffy knew this (and if it motivated his murder of Walsh if he did): Walsh was also involved in the Sterlings' drug shipping empire. Yeah, Walsh is a classical Hate Sink.
- Bad Boss: Naomi tells Jesse that he forced his subordinates to photocopy all of his campaign posters for Sheriff while he left early.
- Bad Cop/Incompetent Cop: He barely does any work upon his arrival, even scolding Deputy Duffy for interrogating the Sterlings. It's implied that he is aligned with the Sterlings, which makes his behavior either lazy or deliberate. This is confirmed in Chapter 13 when a clue reveals that he was involved in their drug trafficking scheme.
- Boom, Headshot!: Duffy shoots him in the head when he reveals himself as the killer.
- Dirty Cop: He was involved in the Sterlings' drug smuggling scheme.
- Fat Bastard: Portly and a perpetual Jerkass.
- Hate Sink: While Jeff Duffy and most of the Sterlings have humanizing qualities while still remaining bad per se, Walsh doesn't. He's a Jerkass who tries to impede the investigation of Kate's disappearance, acts rude and condescending towards anyone who isn't a Sterling, arrests Kate after falsely accusing her of faking her kidnapping and killing Tanner, and participates in Pierce and Margaret's drug trafficking scheme.
- Inspector Javert: He is one of the main antagonists, openly disregarding Jesse and Naomis concerns, trying to place Kate as the villain. After Kate is rescued, he accuses her of murdering Tanner and handcuffs her to her hospital bed despite the fact that she is a potential victim.
- Politically Incorrect Villain: He does racial profiling on the Emersons and gives Naomi crap for being a Native and a woman in a mans job.
- Villains Want Mercy: After his arrest, he pleads with Jesse to write an article supporting his release. He does this again to Duffy shortly before the latter shoots him dead.
Deputy Jeff Duffy nee Taylor Acosta
A deputy of the Birchport Police Department
- Bad Cop/Incompetent Cop: While Walsh is the Bad, Duffy is the Incompetent until The Reveal shows that he is faking his incompetence and actually worse than Walsh.
- Bad Guys Do the Dirty Work: Textbook case; while himself the Big Bad, Duffy is actually the one to take out and bring karma to pretty much all of the other antagonists of the book. It is stated in the epilogue that Birchport is a much better place now that the Sterling line has been ended, and that the police force is no longer corrupt thanks to Walsh being out of office. Duffy deserves credit for both of those things; he killed off the Sterling bloodline and he is the one who took out Walsh (granted, Walsh was already imprisoned).
- Bastard Bastard: The illegitimate son of Pierce Sterling and his secretary Alanis Acosta seeking to avenge his mother's murder by kidnapping Kate, killing his half-brothers Tanner and Bryce, and eliminating the Sterling family.
- Big Bad: He's the one behind all of the story's events, including engineering Kate's kidnapping, murdering his half-brothers Tanner and Bryce, then killing Walsh and Margaret.
- Bitch in Sheep's Clothing: He is the one behind Kate's kidnapping and behind five (six if you don't save Nikolai) murders.
- Character Death: You can choose to let both him and Pierce die, or choose to save one of them, in the 15th chapter.
- Expy: Of Doofy Gilmore from Scary Movie. They're both dumb cops who are murderous psychopaths all along and fool others around them by Obfuscating Stupidity.
- Extreme Doormat: He always lets Walsh walk all over him and is essentially relegated to being Walsh's secretary and whipping boy.
- Fingore: In Chapter 15, the detonator in his hand is shot off by Naomi, which also takes off his hand.
- Green-Eyed Monster: His main motivation for killing the Sterlings is that he is jealous of the life he was denied by Margaret.
- I Did What I Had to Do: He was sent to the lighthouse to investigate a joyrider, and then shot Nikolai for pointing his gun at Jesse, Grant, Flynn, and Naomi. The reveal that he is Taylor Acosta cast this in a new light.
- Manipulative Bastard: See Obfuscating Stupidity below.
- Mistreatment-Induced Betrayal: After his true identity is revealed, he shoots Walsh as payback for the way Walsh always treated him.
- Never Found the Body: Kate comments in the epilogue that there's a part of her that wonders if Duffy is still alive if you chose to save him... But it's never explicitly confirmed if his body was found.
- Obfuscating Stupidity: All of his behavior is a facade to hide a very scary, ruthless, and competent mastermind.
- Pet the Dog: He kidnapped Kate because he saw some goodness in her and wanted to protect her from being corrupted by the Sterlings. His attitude changes when he learns that she is pregnant with Tanner's child.
- On a similar note, rather than killing Jesse in the police station, he locks him/her inside a cell and destroys their phone.
- If saved, it'll be stated in the epilogue that he became a model inmate in prison.
- Pyrrhic Villainy: Sort of, and also a light case of The Bad Guy Wins. Duffy's primary goal was to eliminate the Sterlings. Duffy succeeded in eliminating Bryce, Tanner and Margaret, and he either kills Pierce or Pierce dies in prison. Depending on the player's choices, he also may have succeeded in killing Nikolai. Despite Duffy either dying or finding himself inside a jail cell, he still ultimately succeeds in his goal of terminating the Sterling bloodline.
- Ridiculously Average Guy: Initially, Duffy doesn't stand out that much because he barely has a line of dialogue. Walsh won't even let him interrogate people without his permission. It's all an act though.
- Rule of Symbolism: His badge and name tag are flipped backwards as merely subtle hints of his stupidity. When his true nature is revealed, they're flipped in the right direction to indicate he was faking his stupidity.
- Slasher Smile: He has one these in Chapter 14... and it is terrifying.
- Walking Spoiler: His true role in the story is this! Yeah, have you noticed the large amount of spoiler tags in this section?
- What the Hell, Hero?: Everyone's reaction when he shoots Nikolai. Certain choices will lead to Jesse snapping at him and calling him an idiot. The reveal that he is actually Taylor Acosta proves that he knew exactly what he was doing.
- Woobie, Destroyer of Worlds: His mother was killed by Nikolai under Margaret's order, he was abused and bullied when he was raised as a Foster Kid, and he works under Chief Walsh, not to mention that the Sterlings and Walsh are all asshole victims.
- "Well Done, Son!" Guy: Despite his hatred of all the Sterlings, he gets second thoughts when Pierce tries to convince him to repair their relationship, even crying at the thought, ruining all his revenge plans.
Tino ThompsonA special investigator who works for the state
People from Birchport
Eleanor HarlenayOwner of the local Bed and Breakfast
- Bi the Way: She has dated men and women, and currently has a wife.
- Cool Old Lady: By all her comments, she is one of the few people who is on Jesse and Kates side, and apparently had a crazy lifestyle in her youth.
- The Fashionista: All of Jesses premium outfits are provided by her.
A Russian lighthouse keeper
- Affectionate Nickname: He is very fond of Kate, who he calls Katerina
- Animal Motif: A red octopus, which symbolizes his past that continues to haunt him to the present day.
- The Brute: He is a large Russian man who guards the lighthouse, who also happens to be an enforcer between the Sterlings and the Russian mob.
- Even Evil Has Standards / Wouldn't Hurt a Child: He can't bring himself to kill Alanis's baby son Taylor, which came back to haunt Nikolai hard when Taylor grew up to be Duffy and shot him in the back, potentially killing him.
- Karmic Death: If you don't save him, he is shot by the son of a woman he killed decades ago.
- Love Makes You Evil: Because he loved Margaret Sterling, he obeyed her when she ordered him to burn down Alanis Acosta's house.
- The Mafiya: He's an enforcer and middleman for the Russian mafia in establishing the Sterlings' drug business.
- Sadistic Choice: A special, somewhat out-of-universe case; you have to pay diamonds (the ingame currency for Choices) in order to save his life.
Tony RezA dockworker and small-time criminal with a known grudge against the Sterlings
- Red Herring: The pre-release sneak peeks cover his face until his debut to indicate his shadiness, which isn't helped by his suspicious behavior at the 4th of July Gala. Turns out he isn't the Big Bad; Duffy is. Rez was only at the gala to pick pockets.
D.A. Mac HornbyThe District Attorney of Birchport and a close associate of the Sterlings
- Amoral Attorney: He delivers false testimony about Kate being a Gold Digger during her trial, tries to discredit Jesse as a reliable eyewitness, and manipulates the testimonies of other eyewitnesses to ensure Kate's incarceration. Flynn adds that he's a frequent guest at the Sterlings' parties, implying that he's under their influence.
Judge Samantha Winters
The judge who presides over Kate's bail hearing
- The Cameo: She appears in The Senior Chapter 6 presiding over Becca's mock trial.
- Cool Old Lady: She's involved in a relationship with Miss Harlenay, and despite her stern demeanor, she and Eleanor apparently love to party together.
- Reasonable Authority Figure: She has a reputation for being tough but fair. At Kate's first hearing, she calls Hornby out several times for his unprofessional behavior.