Veronica "Roni" Rawlings
A Chicago teacher's union delegate and Harry's wife.
- Crazy-Prepared: She's highly meticulous, which comes in handy for the heist. Then again, most of the heist was planned for her in Harry's notebook.
- Happily Married: Throughout the film there are brief flashbacks to some heartwarming interactions with Harry. This, combined with her grief at his death, establish them as having a good marriage. Then it's subverted with the reveal their marriage fell apart following the death of their son, and Harry decided to abandon her by faking his death so he could start a family with his new lover and son.
- Heroes Love Dogs: Veronica has a pet dog that she cares about dearly.
- Ice Queen: She acts cold and domineering towards her teammates for most of the movie. The final shot of the movie shows she's become warmer.
- Jerk with a Heart of Gold: Veronica's a good person at her core, but you wouldn't know it from her ice-cold behaviour.
- Kick the Dog: She's at her most unsympathetic when she bullies and slut-shames Alice, assuming she's a Dumb Blonde who Really Gets Around largely due to her appearance and Veronica's own biases.
- Noble Bigot: Reveals she never expected to marry a white man, and is particularly vindictive against Alice, the only white member of her crew. She gets better and treats Alice as a real friend.
- Outliving One's Offspring: Her and Harry's son, Marcus, was killed by racist cops in a traffic stop when they mistakenly thought he was going for a gun.
- Took a Level in Badass: From a teacher's union delegate to an efficient, ruthless burglar who kills her own formidable husband.
- When She Smiles: Veronica spends the entire film in a state of grief and/or anger. Her bright smile at the end is heartwarming to witness.
A clothing store owner.
- Action Mom: Linda is a mother of two who participates in the eventual heist.
- Mock Millionaire: While not quite that rich, Linda learns the hard way she falls into this category. She assumed she was doing well with her shop and always giving the monthly lease payments to her husband to pay off as well as the takes from his robberies. It turns out he just spent all that money at the racetrack and made a slew of bad gambles. Linda had no idea until she comes to her shop to find a bunch of gangsters tearing it up, telling them that her husband sold them the deed to pay off his debts but still died owing them a lot, so they're just cleaning her out. This instant bankruptcy pushes Linda to join Veronica's plan.
- Obnoxious In-Laws: Linda's mother-in-law is a stone-cold bitch who blames Linda for her son's own poor decisions with regards to pursuing a life of crime and subsequent death, saying his blood is on Linda's hands.
A woman who's been abused for most of her life, either by her mother or her husband.
- Abusive Parents: Her mother Agnieska is a vicious piece of work who belittles her emotionally, abuses her physically, and manipulates her into doing things she doesn't want to do purely for Agnieska's own benefit. It's little wonder how Alice ended up in an abusive marriage.
- Broken Bird: She's meek and unassuming due to a lifetime of abuse at the hands of her mother and later Florek. She's manipulated by David and even Veronica is ruthlessly mean to her.
- Country Matters: She stands up to Veronica by calling her this after she's had enough of being underestimated.
- Hair of Gold, Heart of Gold: Alice is blonde and a very sweet person.
- High-Class Call Girl: Her mother convinces her to become one of these.
- Ms. Fanservice: She has a nude scene and dresses in some very flattering outfits.
- Only a Flesh Wound: Averted. She's shot by Tom Mulligan, and while the wound doesn't prove fatal, she's incapacitated almost right away and is unable to continue the heist. Linda has to bring her to a hospital, and although she's later seen alive, it seems a few weeks have passed.
- Statuesque Stunner: Alice is tall and gorgeous, and uses that to her advantage.
- Took a Level in Badass: She's perhaps the most pronounced case of all the widows. She's a meek Broken Bird, but transforms into a stone-cold badass who's able to think on her feet.
- Wounded Gazelle Gambit: To buy a gun, she throws on a flawless Polish accent and approaches a woman and her daughter at a gun show, pretending she's a mail-order bride on the run from an abusive husband. Sympathetic, the woman helps her buy several glocks for each room in her home.
A widow who isn't involved in the robbery due to being too busy with her newborn baby.
Veronica's husband and a renowned bank robber with connections to politicians.
- Big Bad: Harry's revealed to be the true villain of the film, having faked his death, betrayed his partners, and abandoned his wife to his enemies so he could start a new life with his lover and secret child. At the end of the movie, he comes to steal the money from Veronica and even tries to murder her.
- Bitch in Sheep's Clothing: Though he's a thief, Harry seems like a loving husband and a good leader to his men. It turns out, not only did he have all his accomplices killed so he could fake his death, but in the end, he's willing to murder his wife to take the money she stole.
- Despair Event Horizon: His son Marcus' shooting death at the hands of a racist cop, which Harry heard as he was talking to his son on the phone, not only destroyed Harry and Veronica's marriage, but made him decide to fake his death and leave everything including Veronica behind, running off with a friend of Veronica whose husband also died in the heist and whose son he fathered.
- Even Evil Has Loved Ones: He's a thief, but flashbacks show he really loved his wife and son. Even though he leaves Veronica at the mercy of his enemies, he planned for her to sell his notebook to get out of debt with Jamal. After Veronica decided to carry out one of his heists to pay off the debt instead, Harry's clearly remorseful about what he's done, but it's not enough to stop him from trying to rob and kill her.
- Faking the Dead: Harry worked with Jack Mulligan to fake his death so Harry could run off with his new family.
- Happily Married: Flashbacks to their marriage show Veronica and Harry having a very loving relationship. Subverted when it's revealed their marriage fell apart after the death of their son, and Harry faked his death so he could run out on Veronica with his new family.
- It's All About Me: Harry's ultimately revealed to only care about himself when he shows up to rob Veronica in the climax. He feebly tries to justify his actions by claiming he couldn't save their relationship, so he had to focus on saving himself.
- Outliving One's Offspring: His son, Marcus, was shot by racist cops who thought he was going for a gun during a traffic stop. Making it even worse, the reason Marcus was pulled over was because he made a U-Turn after Harry called him and told him to come home because he left Veronica's anniversary present in the car.
- Posthumous Character: He only appears in the opening scene and a few brief flashbacks but his presence looms large over the story even after his death. Then subverted with the reveal that he's alive.
- Walking Spoiler: Not only is Harry still alive, but he's been cheating on Veronica with Amanda, and Amanda's baby is actually his own.
Linda's husband who is a gambler and one of Harry's partners.
- The Gambling Addict: He was a severe gambling addict, and put his money not into his family, but into his addiction. This leaves Linda in severe debt.
Alice's abusive husband and one of Harry's partners.
Amanda's husband and one of Harry's partners.
- Cuckold: It is revealed that his wife Amanda not only cheated on him with his boss, but also fathered a child with him, and the two of them arranged Jimmy's death so they could be together.
- The Generic Guy: While all the other husbands have some traits no matter how minor that characterizes them to some degree, Jimmy doesn't really have anything that stands out. The only thing notable about him is that his wife is cheating on him with Harry.
A crime boss and politician to whom the widows are indebted.
- Big Bad: Harry robs Jamal in the beginning of the movie, and Jamal responds by forcing Veronica to pay back the $2 million he stole or face the consequences. Later revealed to be a member of the Big-Bad Ensemble with Harry and Jack Mulligan.
- Corrupt Politician: He aspires to a life of politics explicitly for the kick-backs.
- Fat Bastard: He's an overweight crime boss who wants to make the jump to corrupt politician.
- Jerkass Has a Point: While he tries to intimidate Veronica into selling her expensive penthouse to get back the millions her husband stole, he's right that it was paid for with criminal activities that she never had issue with.
- Karma Houdini: Zigzagged. Jamal doesn't suffer any legal repercussions for his crimes and even gets the $2 million back from Veronica, but he loses the race for alderman to Jack Mulligan as an indirect result of the widows' heist, and his brother/enforcer, Jatemme, is killed when he tries to take the stolen money from the widows.
- Kick the Dog: A near literal example. When he comes to threaten Veronica to pay back the money her husband stole, he intimidates her by briefly dangling her small dog by the leash around its neck.
- Pragmatic Villainy: Jamal puts restrictions on how much blood Jatemme can shed, not for moral reasons, but because he doesn't want him to call attention to them during his campaign. Hell, the entire reason he wants to go into politics is because it can make him just as much money, while being far safer.
- Siblings in Crime: He's a mob boss whose little brother is his top enforcer.
Jamal's brother and mob enforcer.
- Dissonant Serenity: Jatemme almost always presents a calm, laid-back demeanor, even when he commits horrific acts of violence, like torturing the paralyzed Bobby Welsh by stabbing him in the legs and back to see where Bobby can and can't feel pain.
- The Dragon: He's Jamal's top enforcer in their criminal organization.
- Dropped a Bridge on Him: Most of Jatemme's scenes build him up as a terrifying psychopath who's a threat to nearly everyone around him. In the end, he dies when he's rear-ended by the widows while trying to steal their haul and crashes the van he's driving.
- Psychopathic Manchild: His frequent acts of petty cruelty and open boredom in any activity not involving violence or crime makes him come across as this.
- Sadist: Unlike Jamal, who at least is pragmatic in his dealings, Jatemme takes delight in hurting other people, usually prolonging their suffering before killing them.
- Siblings in Crime: He's the top enforcer for his mob boss older brother.
- You Have Failed Me: He executes the two men who failed to protect Jamal's money from Harry, but takes the time to toy with them first, forcing them to recite the rap they were found singing before murdering them.
A politician who finds himself mixed up in the widows' plans.
- A Lighter Shade of Black: Jack might be corrupt, greedy, and even mildly racist, but he's a saint compared to his monstrous father. The city is much safer in his hands than it is in the hands of Tom or the murderous Jamal.
- Big-Bad Ensemble: It's revealed Jack was the one who hired Harry to rob Jamal to cripple his campaign.
- Bitch in Sheep's Clothing: He displays an image on the campaign trail as a progressive politician who recognizes the value of Americans of all races. In private, he is racist and homophobic, frequently putting down his opponent Jamal in attempt to pump himself up. During one public event, he poses with black women he boasts he made into independent business owners, but ignores a reporter's request to speak about the claims that he's been embezzling from those same women. Then upon getting in his car, Jack starts ranting about "encroaching" black communities right behind the chauffeur of his car, who is also black.
- Corrupt Politician: The only difference between Jack and Jamal is that Jack is not an outright mob boss. Otherwise, he's just as corrupt and self-interested, and just as willing to stoop to murder.
- Freudian Excuse Is No Excuse: At one point, Jack goes into a self-pitying rant to his campaign manager, talking about how he never wanted a life in politics and was forced into it as well as his ensuing corruption. His campaign manager rightfully calls him out on being a whiner, as everyone has a sob story and most are worse than his.
- Karma Houdini: Like with Jamal, it's zigzagged. Jack faces no legal repercussions for his criminal actions and even ends up winning the race for alderman, but he actually hates working in politics, has $5 million stolen by the widows, and his father ended up killed during the heist, which may or may not be a good thing for Jack, depending on how candid he was when saying he wanted his racist, abusive father dead.
- Pyrrhic Victory: Even though he wins the race for alderman, Jack hates politics and never wanted a career in it, plus he's out $5 million and his father's dead, though he might be happy about that last one.
Jack's father and a power broker at odds with his son.
- Abusive Parent: To his son, Jack, whom he verbally abuses and threatens to beat. His son pretty much tells him he can't wait for him to die.
- Asshole Victim: He's the only casualty of the heist the widows commit. For anyone else, it would be a tragedy that an old man is killed during a robbery, but given that he's a virulent racist, abusive father, and corrupt politician, the only people who give a damn are the people who don't know him.
- Bitch in Sheep's Clothing: He presents himself as a cheerful, grandfatherly figure, while really he's a corrupt, racist monster.
- Corrupt Politician: He's the former alderman and was even more corrupt than his son.
- Evil Old Folks: He's a viciously racist and bitter octogenarian.
- Racist Grandpa: Tom is an elderly bastard who's so racist that even his own racist son says he can't wait for his father to die so he won't have to deal with people like him anymore.
- Villain with Good Publicity: A scandal or two aside, he's seen as a city institution. Too bad he doesn't give a damn about the city, viewing it only as a tool by which to satisfy his desire for power, status, and his family legacy.
Jack's young campaign manager.
- Honest Advisor: She's unafraid to speak her mind to Jack when he's being a self-pitying mess.
- The Man Behind the Man: As the scene in Jack's car shows, Jack hates the political life and the burden of his family's legacy. He almost folds, except that Siobhan scolds him and tells him to man up. She's got the ambition and grit that fuels the campaign. One gets the sense that she'll be holding all his strings in a few years, if indeed she isn't already.
- Stepford Smiler: Downplayed, because she isn't smiley to a creepy degree. Her persona is polite, calm, and smiling, often fading into the background. A lot of awful sexual remarks come her way, and she has to take it in stride.
A babysitter and beautician who looks after Linda's children that works with Veronica's group.
- Action Mom: Like Linda, she's a mother who joins the widows on a heist.
- Getaway Driver: Belle is brought in to be the getaway driver for the robbery after Jatemme kills Bash.
- Sixth Ranger: She's not a widow of one of Harry's associates, but she joins the other women on the heist halfway through the film.
- Struggling Single Mother: Belle's forced to take multiple jobs to provide for her daughter and barely gets to spend any time with her.
- When You Coming Home Mom: Belle isn't able to spend as much time with her daughter as she wants because she's forced to take jobs at all hours to make a living.
Alice's abusive mother.
- Abusive Parents: She physically and emotionally abuses her daughter, then pressures her into becoming a High-Class Call Girl.
- Gold Digger: Agnieska believes it's a husband's role to give her wife everything she wants, and tries to pass this onto her daughter, explaining how Alice ended up with someone who provided for her, but also abused her.
The Rawlings family chauffeur.
- Ambiguous Disorder: Bash is referred to as "simple". He seems to forget things very easily, he speaks very carefully and numerous pill bottles are seen at his apartment. It's implied he might have some kind of brain damage from his career playing football.
- The Driver: He's Veronica's chauffeur throughout the movie, and Veronica plans on using him as the getaway driver for their heist. Unfortunately, he's murdered by Jatemme before the heist can take place.
- Morality Pet: He serves as one to Veronica. She usually treats him with more compassion than she does most people she interacts with.
- Sacrificial Lamb: Bash is murdered by Jatemme to show the Mannings aren't playing around.
- Undying Loyalty: To Veronica and Harry. It gets him killed.
A corrupt cop involved in a conspiracy.
- Dirty Cop: He's in on faking Harry's death.
A real estate worker who Alice sells herself to following Florek's death.
- Bitch in Sheep's Clothing: He's seemingly kind to Alice, letting her take her time on moving toward sexual activity and using his connections to help her with the blueprint she's investigating. But he is still in a relationship with her based on around keeping Alice indebted to him with money and he sees nothing wrong with that, claiming to view all life as based around transactions. When Alice appears to warm up to him and asks, after multiple liaisons, if she could move in with him, he tries to divert the question and tells her only to care about all the money he's giving, implying he is still married.
The CEO of a security company.
- Dirty Old Man: He's having a sordid affair with a woman young enough to be his daughter. As it turns out, she's his niece.
A bar owner and contact of Harry's.
A popular reverend who can tip the balance of the election for alderman.
- Sinister Minister: He shows zero compunction about using his hold over his congregation to sway the political fortunes of the city.