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Sullivan
Michael Sullivan, Sr.
A top-notch hitman who works for John Rooney.
- Anti-Hero: A darker example. He intends to save his son's soul so he wouldn't end up like him through pragmatic means.
- Badass and Child Duo: He's the badass to his son's Child.
- Badass Longcoat: He's usually seen wearing one of these.
- Contract on the Hitman: He works as Rooney's right-hand man and top killer, only for Rooney and Nitti to put a hit on him because he won't give up his vendetta against Connor for killing his wife and son.
- The Dragon: To John Rooney, as Rooney's right-hand man and enforcer.
- The Dreaded: The name Sullivan carries quite a bit of weight in the criminal underworld, as shown when he shows up to collect from Tony Calvino and once he gives his name he's let in at once.
- Even Evil Has Loved Ones: He's a hitman as well as a loving father and husband.
- Everyone Has Standards: Even though he's a mob enforcer that doesn't mean he's completely abandoned his moral code. He calls out Connor for murdering Finn McGovern when they were just ordered to talk with him, and when he robs a mob bank, he threatens the manager that he better not find out he just took the savings of starving farmers.
- Evil Parents Want Good Kids: He'll damn his own soul to Hell if it means saving his son's soul.
- The Hero Dies: He succeeds in getting his revenge against Connor Rooney, and Nitti agrees to call off the hit on him. Only for Maguire to mortally wound him anyway as revenge for disfiguring his face. Sullivan lives just long enough to save his son and kill Maguire before succumbing to his wounds.
- Hitman with a Heart: He'll kill on Rooney's orders but he obviously doesn't relish doing so, and he's motivated by a desire to ensure his children don't end up like him.
- Manly Tears: Sullivan is on the verge of tears when he raises his Tommy gun to John Rooney.
- More Dakka: His heavy weapon is a Tommy gun.
- Outliving One's Offspring: Connor kills his younger son, Peter, mistaking him for Michael Jr.
- Patricide: Killing his Parental Substitute John Rooney.
- Professional Killer: Sullivan's job is as a mob hitman for the Rooney family.
- Revenge Before Reason: He has many opportunities to just leave with his son but, ultimately, is unable to let go of his need for revenge.
- Robbing the Mob Bank: After Maguire makes his first attempt to kill him, he starts robbing banks for their dirty money only in the hopes that threatening their profits will convince Capone to give up Connor.
- Shell-Shocked Veteran: It's implied that his service in the first world war might be part of the reason behind his stony presence and willingness to kill people.
- Too Much Alike: His reason given for why he subconsciously treated his elder son differently than Peter. Michael Jr. reminded him too much of himself and he didn't want him to end up like him.
- Walking Armory: He usually brings a Tommy gun, a Colt M1911 semi-automatic, and a Colt Detective Special as a backup weapon.
- "Well Done, Son" Guy: His sons have this dynamic with him and Sullivan has this dynamic with Rooney, his surrogate father. All his criminal efforts are a means to pay Rooney back for everything Rooney's done for him.
- White Shirt of Death: Wears a white shirt when he is killed by Harlen Maguire.
- You Remind Me of X: He tells Michael Jr. that he treated him differently because he reminded Sullivan of himself.
Michael
Michael Sullivan, Jr.
Played By: Tyler Hoechlin
Michael Sullivan's son.
- Badass and Child Duo: The Child to his father's badass.
- Broken Pedestal: When he sees his father killing someone.
- Comically Small Demand: While not too small, given the time period, but this is invoked When he asks his father for a $200 share of their robberies then frowns and asks if he should have asked for more and is told he'll never know now that the deal is done.
- Cool Big Bro: He's patient and caring towards his younger brother Peter.
- Drives Like Crazy: Justified. He's a kid who has to serve as a getaway driver because his father can't trust anyone else and obviously he's not perfect at it.
- Sole Survivor: Of the non-historical characters, and his family.
Rooney
John Rooney
Played By: Paul Newman
A crime boss who treats Sullivan as a surrogate son.
- Affably Evil: He's respectful towards everyone he deals with and tries to avoid unnecessary bloodshed whenever possible. He truly doesn't want Sullivan dead, and only orders a hit on him because he loves his son too much to let Sullivan kill him.
- Anti-Villain: He's not a good man, but his sincerely kindly, grandfatherly personality and sincere standards make him quite sympathetic.
- Beware the Nice Ones: Even though he's a crime boss, his soft-spoken, affable and understanding nature practically makes him a Reasonable Authority Figure. However, he's still a crime boss so he has no problem ordering hits when he thinks it necessary, even if it's against his surrogate son.
- Big Bad: The source of much of the conflicts in the film, such as Mike Sr.'s corruption years ago, Connor's Daddy Issues, and hiring Harlen Maguire.
- The Don: He's an Irish crime boss allied with the Chicago Mob who rules Rock Island like a god.Finn McGovern: You rule this town as God rules the Earth. You give, and you take away.
- Even Evil Has Loved Ones:
- Despite all of his screw-ups, Rooney loves his biological son, Connor, and will do anything to protect him from Sullivan's wrath. Even when Sullivan reveals Connor has betrayed Rooney by stealing from him for years, he still won't give up his son.
- Even though he ends up ordering a hit on his surrogate son, Sullivan, to protect Connor, it's clear he still cares about him and tries to give him every opportunity to let the grudge die so Rooney can spare his life. When Sullivan comes to kill him, Rooney tells him he's happy he's the one doing it.
- Even Evil Has Standards:
- He orders a hit on his surrogate son, Sullivan, to protect his biological son from his wrath. However, he refuses to order a hit against Michael Jr., regardless of the threat he could pose in the future or what he's seen, because he's a child.
- On a lesser note, Rooney also refuses to get the mob involved in the labor unions:
"What men do after work is what made us rich. No need to screw them at work."- He's aghast at Michael's hypocrisy and sense of moral superiority when he states his reasoning for why he wants to murder his son:
Michael: He murdered Annie and Peter!Rooney: (raising his voice) There are only murderers in this room! - Evil Old Folks: An old Don who is still a large presence in the criminal underworld.
- Face Death with Dignity: When he realizes that Sullivan's comes to kill him, he just bows his head in resignation as his men are gunned down, then turns around and tells his surrogate son that he's glad Sullivan is the one to kill him.
- "Facing the Bullets" One-Liner: "I'm glad it's you."
- Honor Before Reason: He won't give up his son, no matter how justified Sullivan is in his vendetta or how much easier it would make Rooney's life overall.
- I Wished You Were Dead: When he finds out what Connor did to the Sullivans, he begins beating him while saying he curses the day Connor was born, before realizing what he's just said and hugging him in remorse.
- No-Holds-Barred Beatdown: Inflicts one on Connor when he discovers what his son did to Annie and Peter. Complete with Punctuated Pounding.Connor: Pa, I'm sorry.
John: Stupid!
Connor: The kid would have talked. I'm sorry.
John: Goddamn you. Goddamn you! (punch) I curse... (punch) The f***ing... (punch) Day! (punch) You were born. I curse it! - Parental Substitute: He's treated Michael Sr. like a son, explaining the latter's loyalty to him.
- Pet the Dog: The only times he's ever non-villainous are when he behaves as a kindly grandfather to Mike's children.
- Sadistic Choice: Either Rooney stands aside and lets his surrogate son Michael Sr. kill his biological son Connor in revenge for the deaths of Michael's wife and son, or he protects Connor by trying to kill Michael or drive him into exile. It's even worse because it's also a Morton's Fork; Connor is too incompetent and vicious to be trustworthy, which means once his father dies he is a dead man walking. Rooney still chooses to defend his biological son regardless.
- Thicker Than Water: Despite what Connor has done, he still protects him.
- This Is Gonna Suck: "Lord help us."
- "Well Done, Son" Guy: He's the father figure that his biological son, Connor, and surrogate son, Sullivan, both try to impress.
- Would Not Hurt A Child: He refuses to put a hit out on Michael Jr. despite the risk he poses.
Maguire
Harlen Maguire
Played By: Jude Law
A crime scene photographer who moonlights as an assassin.
- Bald of Evil: The hair's thinning on the top of his head and he is an amoral Professional Killer.
- Coin Walk Flexing: He has a habit of doing a coin walk when he's bored or frustrated.
- Composite Character: There was no single hitman after the Sullivans in the graphic novel, with them simply having to deal with various cardboard bad guys. The writer admitted creating a single character for this purpose was a big improvement.
- Creepy Souvenir: The photographs he takes of the murders he's committed. He hangs them on the walls around his apartment.
- Dastardly Dapper Derby: Amoral Psycho for Hire Maguire wears a brown bowler hat that contrasts with most of the fedora-wearing mob cast.
- Dies Differently in Adaptation: In the graphic novel, Michael Jr. shoots him. In the film, Michael Sr. shoots him.
- Dragon Their Feet: Technically he's Nitti's dragon, but he's the final threat faced in the film who kills Sullivan after Rooney and Connor have been dealt with and Nitti ends the feud.
- Establishing Character Moment: He arrives as his legitimate job as a crime scene photographer to take pictures of a dead man. When he's alone, it's revealed the victim is still alive, so Maguire calmly suffocates him to death so he can carry on with his pictures.
- Faux Affably Evil: Seems quite cordial with Mike before he makes his intentions known.
- Hero Killer: Murders Mike Sullivan Sr. at the end of the film.
- Implacable Man: Severe injuries, the death of his employer, and the hit being called off don't stop him from coming after the Sullivans.
- It's Personal: He kills Mike Sr. even after the hit is called off because he scarred his face.
- Mad Artist: To an extent. In addition to assassination, he also takes pictures of his victims which he both sells to make extra money and keeps as part of his personal gallery.
- Psycho for Hire: He's an assassin with a fascination with death to the point that he doubles as a crime scene photographer so he can take pictures of the dead and dying. In a conversation with Sullivan, he says he's lucky to do what he loves for a living.
- Shotguns Are Just Better: Wields a Winchester 1897 shotgun during the hotel shootout.
- Sinister Sweet Tooth: A psychopathic assassin who enjoys his coffee with a lot of sugar, and has the brown teeth to prove it.
- Troll: He baits and teases Mike Sr. some during their encounter with Bait-and-Switch Comment's before revealing his true nature.
- Unfriendly Fire: Accidentally kills Alexander Rance in the hotel shootout.
Connor
Connor Rooney
Played By: Daniel Craig
The unstable, violent son of John Rooney. He is jealous of the surrogate relationship between his father and Sullivan.
- Adaptational Heroism: The film version isn't a pedophile at least.
- Adaptational Wimp: In the comic he's killed in a shootout with Sullivan, int he comic, he's merely shot while taking a bath.
- All for Nothing: He killed the McGoverns and the Sullivans to cover up the fact that he's been stealing from his father. However, his father already knew, and all Connor's actions did was ensure his death and Rooney's own.
- Big Bad Wannabe: He's a much smaller deal than he seems to think he is and despite being the one who instigates the plot he relies on others to keep himself out of trouble.
- Deadly Bath: Given a Boom, Headshot! by Michael Sr. while in a bathtub.
- Defiant to the End: In the comic he tells Sullivan to go to hell before his death.
- Dirty Coward: Connor is quick to kill people when he has someone armed and ready at his side (like Michael Sr. in the scene where he meets with Finn McGovern) but isn't that much on his own when not trying to kill unnarmed women and children.
- Evil Is Petty: Tries to murder Michael Jr. just because he thinks the boy will rat him him out, even though Michael Sr. has sworn his son to secrecy.
- Foil: Mike and Connor are Rooney's surrogate and actual son, respectively, but couldn't be more different if they tried.
- Mike is a Hyper-Competent Sidekick to the Rooney family, and The Dreaded to not just Rooney, but the entire underworld; Connor is a Dirty Coward and The Load to both his father and the Chicago Outfit.
- Mike is a quiet family man and The Stoic; Connor is a Psychopathic Manchild and Stepford Smiler.
- Green-Eyed Monster: His jealousy of Michael Sr. is at the core of his issues.
- He Knows Too Much: In order to cover up the fact that he's been stealing from his father, Connor tries to have Sullivan killed and personally goes to murder Michael Jr., killing Annie Sullivan in the process, because they know too much. The only reason Michael Jr. survives is because Connor mistakes Peter for him. And for additional irony his father knew all along that Connor had been stealing from him, so the deaths were completely pointless.
- Inadequate Inheritor: He's next in line to inherit his father's criminal organization when he passes on, but compared to his father he's incompetent and unstable to the point where Nitti gives him up to Sullivan after Rooney's killed.
- Karmic Death: Murdered Annie and Peter while the latter was taking a bath. Michael Sr. kills Connor the same way.
- The Load: The Chicago Outfit views him as a liability and only protect him because of John. When Michael kills John, Nitti has no problem selling out Connor.
- Murder Is the Best Solution: Killing people is Connor's preferred way of handling problems. Despite how useful they are to his father, Connor kills the McGoverns and the Sullivans when he thinks they could be an inconvenience.
- Obfuscating Stupidity: He appears to murder Finn McGovern in a fit of impulsive rage, but after the ledgers are found, it's revealed that Connor meant to kill McGovern all along as a coverup for the money he's been stealing.
- Psychopathic Manchild: Of the whiny, petulant type. Just see him whimpering and cowering when his father learns what Connor did to Annie and Peter Sullivan.
- Psychotic Smirk: Which does him no favors when his father asks for an apology at a meeting.John: You would like to apologize? Try again.
- Stealing from the Till: He's been stealing money from his father via people he's killed, like the McGoverns.
- Stepford Smiler: He tries to be in the beginning at least, where he masks his instability and resentment behind a weak grin and awkward jokes. Peter even asks why Connor's always smiling and gets this in response.Connor: (furiously) Because it's all so fucking hysterical.
- Surprisingly Sudden Death: He's a major antagonist who Sullivan spends most of the movie trying to kill out of vengeance for his murdered wife and son. However, Connor's actual death is highly anticlimactic in how abrupt it is, especially when contrasted with his father's dramatic death. Sullivan just unceremoniously shoots him in the head while Connor's taking a bath. To emphasize the point, Nitti's men actively allow Sullivan to kill Connor, standing aside or even opening doors for him.
- The Unfavorite: His father clearly prefers his surrogate son, Sullivan, over him. However, despite how much Connor disappoints him, his father still loves him to the point where he takes a hit out on his surrogate son to protect his biological son.
- "Well Done, Son" Guy: Connor clearly wants his father's love and respect but his incompetence and instability only makes him a screw up who only gains his father's disappointment.
- Would Hit a Girl: Murders Annie Sullivan while trying to kill her son.
- Would Hurt a Child: When Michael Jr. watches him murder Finn McGovern, Connor tries to cover his tracks by killing the witness. Instead, he murders Peter by mistake.
Nitti
Frank Nitti
Played By: Stanley Tucci
The underboss for the Al Capone Outfit.
- Know When to Fold Them: As soon as Rooney's dead and protecting Connor is no longer profitable, Nitti tells Sullivan where Connor is hiding and calls off the hit on him and his son.
- Mouth of Sauron: Since Al Capone is never seen in the movie outside of deleted scenes, Nitti serves as his representative.
- Would Hurt a Child: He tries to persuade Rooney to order a hit on Michael Jr. due to the threat the kid could pose in the future.
Annie
Annie Sullivan
Played By: Jennifer Jason Leigh
The wife of Michael Sullivan, Sr. and mother of Michael Jr. and Peter.
- Happily Married: She and Michael Sr. are a very loving couple.
- Senseless Sacrifice: To her credit, she tries to save Peter's life by shielding him with her body. Unfortunately, Connor kills them both anyway.
- We Hardly Knew Ye: Both she and Peter are killed thirty minutes into the movie without much characterization.
Rance
Alexander Rance
Played By: Dylan Baker
An accountant who holds the ledgers for the Rooney crime syndicate.
- The Bait: He's supposedly hiding in a fancy hotel, but it's actually a trap as Maguire is across the road.
- Chekhov's Gunman: Briefly appears early in the film during a meeting with the Rooneys before becoming more relevant when Michael starts robbing banks.
- Sissy Villain: He's a foppish mob accountant.
- Unfriendly Fire: Maguire accidentally kills him by shooting him through the wall of his hotel room.
Kelly
Jack Kelly
Played By: David Darlow
An advisor of Rooney.- Amoral Attorney: He's a lawyer for underworld kingpin John Rooney and is willing to help him protect Connor after knowing he killed Annie and Peter.
- Boom, Headshot!: Shot in the head at point-blank range by Sullivan.
- Bribe Backfire: Attempts to bribe Sullivan with $25000 to leave the country and end the feud. Simply put, it doesn't work.
- Shoot the Messenger: Kelly unhappily delivers a message to Sullivan making to clear that he can't go after Connor and should just leave town. Sullivan is not happy and takes this out on Kelly.Kelly: Think, Mike. Don't be stupid. I'm just the messenger.
Michael Sullivan: [lowers his gun] Then give Mr. Rooney a message for me.
Kelly: What is it?
Sullivan shoots him. - Undying Loyalty: He's loyal enough to Rooney to meet Sullivan alone and without bodyguards, to try and persuade him to end the vendetta despite clearly being aware that Sullivan might kill him.
- Unwitting Instigator of Doom: Kelly mentions that the Rooneys need to collect debts owed by Tony Calvino; when Michael Sr. is sent to collect the debts, Connor seizes the opportunity to murder Michael's family.
- We Hardly Knew Ye: Kelly is only in two scenes, with less than a dozen lines of dialogue.
