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    Ira 

Ira Schermer

Played by: Ben Shenkman
https://static.tvtropes.org/pmwiki/pub/images/is.png
...

Ira is the personal attorney to the Rhoades family, and a good friend of Chuck's for many years.

  • Ascended Extra: The character becomes much more prominent in season two.
  • Et Tu, Brute?: He is incredibly hurt after Chuck sabotages the Ice Juice IPO to trap Axe, which costs Ira his fortune, reputation, and his career. Even though Ira could sue for damages, it would take years and might not even work.
  • Meal Ticket: Dates a staggering number of young blondes after his divorce, and he's quite aware that they're only interested in his money, stating, "You put the Porsche in the Tinder photo. You can't be subtle." However, he confesses that he'd much rather just have a stable, loving relationship like Chuck. He ultimately falls in love with a girl, but seems completely oblivious to the fact that she's also just interested in his money. It turns out that she's in fact been conning him to outright steal his money, but he knew and was hoping that she'd just learn to love him. Eventually, with some help from Rhoades Sr., Ira gets what he wants.
  • Mistreatment-Induced Betrayal: After Chuck's sabotage of the Ice Juice IPO puts a huge strain on his finances, Axe offers Ira $30 million in exchange for not testifying against Axe. Ira agrees and proceeds to reveal Chuck's involvement to Bryan after being called to testify.
  • Nice Guy: Seems a bit too mild to be a lawyer.
  • Took a Level in Cynic: After the Ice Juice situation, Ira has lost all trust in Chuck, even going so far as to testify against Chuck.
  • We Used to Be Friends: With Chuck, as a result of losing his money and livelihood in the Ice Juice fiasco. Ira agrees to not tell anyone about it, but tells Chuck that this is the last conversation they will ever have, which will end at that moment. Subverted later in Season 3 where Ira is willing to bury the hatchet with Chuck, though it is going to be a long time before he can really trust him again.

    DeGiulio 

Adam DeGiulio

Played by: Rob Morrow

"I'm here to ask you the promise you made to me, that there was no favor you'd refuse"

A deputy to the Attorney General, later becomes the federal judge who replaces Wilcox

    Terry & Johnny 

Terry & Johnny Burke

Childhood friends of Lara from the mean streets, now petty criminals and owners of a Bad Guy Bar.

  • Loan Shark: They're leg-breaking loan sharks who are able to extort their deadbeat debtors into some extreme measures.
  • Separated-at-Birth Casting: They look remarkably similar in spite of not being played by brothers.
  • Smug Snake: Times two.

    Sweeney 

"Buffalo" Bob Sweeney

Played by: Matt Servitto

Mayor of Buffalo. Later elected as Governor of New York.

  • Dark Secret: Bob sent his son to a "pray away the gay" camp. Chuck initially uses this to deter Bob from competing with him for the governorship.

    Krakow 

Todd Krakow

Played by: Danny Strong

Head of a hedge fund in competition with Axe Capital. Later appointed as U.S. Secretary of the Treasury.

  • Jerkass: He's a cocksure little sleazeball.
  • Mister Big: Played by the 5'2" Danny Strong and runs his own hedge fund and, later, the Treasury Department.
  • The Napoleon: His detractors mention his short height as being one of the reason's he's so overbearing.
  • No Celebrities Were Harmed: Starts out loosely based on Martin Shkreli, then evolves into a stand-in for Steve Mnuchin, Donald Trump's Treasury Secretary, when he takes the same cabinet post.
  • Politically Incorrect Villain: Lashes out at Taylor and calls them a "freak" and "it" when he loses the poker tournament.

    Boyd 

Lawrence Boyd

Played by: Eric Bogosian

Lawrence Boyd is one of the founding partners of Spartan Ives, the prime broker to Axe Capital. A highly sought-after mind in the finance world, Boyd becomes an ally of sorts to Bobby once Southern starts investigating him.

  • Evil Mentor: To Bobby.
  • No Celebrities Were Harmed: As Spartan Ives is an Expy of Goldman Sachs, Lawrence Boyd is one for their longtime CEO, Lloyd Blankfein.
  • Surpassed the Teacher: When Chuck and the Southern District turn their eye on Boyd, he goes to Bobby and begs for his help in outwitting Chuck Rhoades (as Bobby beat the charges in season one).
  • The Nicknamer: Likes calling Bobby "Roberto".
  • Treacherous Advisor: Shoulda been more careful who you backstabbed, Bobby. Boyd turns state's witness and cooperates with Chuck, playing a big role in the Ice Juice gambit.

    Foley 

"Black" Jack Foley

Played By: David Strathairn

Jack Foley is one of New York's wealthiest and most powerful men. The "Kingmaker" of the political scene, it is he who Chuck has to go to for a chance at winning the governorship. He sinks the Sandicot deal as a favor to his old friend, Rhoades Senior.

  • Blue Blood: His fortune is at least six generations old.
  • The Chessmaster: His influence seems to be having an effect on Chuck as well.
  • Kingmaker Scenario: He's the deciding factor in every political appointment in New York, and the one who awards the casino deal to a different city, landing Sandicot in debt to Axe Capital.
  • Taking You with Me: Upon being diagnosed with terminal cancer, Foley attempts to torpedo Chuck's run for state attorney general by leaking his knowledge of Chuck's sadomasochism to Jeffcoat. Unfortunately for Foley, the move backfires badly when Chuck end-runs him by publicly coming clean about his kinks.
  • Uncle Pennybags: Foley's power comes more from connections and influence rather than straight wealth, but he is still extremely wealthy. He's a Blue Blood who makes a killing in steel. Ben Folds plays at his dinner party.
  • Worthy Adversary: Is impressed by Chuck's maneuvering against him, calling it downright gubernatorial.

    Andolov 

Grigor Andolov

Played by: John Malkovich
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"Survival, in this world, is all."

"If you want to kill the meat, kill the meat. If you only want to eat the meat, get someone else to do the killing."

Russian oil oligarch and organized crime figure whom Bobby wants to invest $20 billion in Axe Capital.

  • …And That Little Girl Was Me: He tells a grim story about a Russian child and its mother, which Bobby later deduces was Grigor himself and his own mother.
  • Attention Deficit... Ooh, Shiny!: While Grigor did not get where he is by being easily distracted in business dealing, he has reached a level of wealth and power where he treats a multi-billion dollar investment as a form of entertainment. Bobby lampshades the fact that if there is no conflict to entertain him, Grigor's attention will soon shift to other business opportunities and he will pull his money out of his current project — in this case Taylor's fund.
  • Bald of Evil
  • Beard of Evil: A goatee in Season 3, developed into a full beard in Season 4.
  • Cool Old Guy: An evil example. His Establishing Character Moment comes when Bobby finds him practicing hockey with the New York Islanders, wearing a custom-made jersey.
  • Deal with the Devil: He's the devil in Bobby's situation.
    How can I keep my money with a man who won't kill for it?
  • The Dreaded: Grigor's reputation is such that even Hall fears him.
  • Expy: Basically an even more powerful and intimidating version of Malkovich's character "Teddy KGB" from the film Rounders.
  • Fiction 500: Comes with the territory if you're a Russian oligarch. He's rich enough that he's considering a purchase of a sports franchise, as Bobby tried to do in Season 2.
  • The Mafiya: Besides being an oligarch, he's also an international figure in organized crime whose power is so vast that Hall states he won't be able to help Bobby if things go south.
  • Make It Look Like an Accident: One of his specialties, so refined that Hall can't help but praise it. Bobby is offered Andolov's "services" to get rid of Taylor. He refuses them.
  • Mother Russia Makes You Strong: Has the archetypal Had to Be Sharp mentality and has disdain for what he views as recurrent American whining.
  • Never Going Back to Prison: Underscores this several times when he starts dealing with Bobby.
  • Playing Both Sides: Agrees to invest in Taylor's new hedge fund at Bobby's expense, while giving Bobby the offer to have Taylor killed for revenge. Bobby doesn't take the offer.
  • Politically Incorrect Villain: Downplayed. Grigor at one point refers to Taylor as "she" rather than their preferred pronoun, which is very much in line with how an old-school Russian oligarch would likely treat a non-binary American. He later does use their preferred pronouns after getting into business with them, which shows that he can be quite progressive for his background if his money is involved.
  • Put on a Bus: Chuck forces Grigor to return to Russia as a favor to Axe after Axe helps Chuck rig the primary election for attorney general.
  • The Rival: Axe views Grigor as the first fellow oligarch who actually overmatches him.
  • Ruthless Foreign Gangsters: While Axe and Rhoades aren't above thuggery to achieve their goals, it pales in comparison of Grigor's level of ruthlessness.

    Jackie 

Jackie Connerty

Bryan Connerty's older brother, a professional safe-cracker.

  • The Charmer: Manages to land his brother's ex, Kate, despite him being a criminal and her an assistant to the state attorney general.
  • Disappointing Older Sibling: Connerty and the rest of his family have been estranged from Jackie thanks to his criminal lifestyle.
  • Foolish Sibling, Responsible Sibling: The Foolish to Bryan's responsible. Bryan is the U.S. Attorney for the Southern District of New York, while Jackie is a career criminal who seemingly lives in the margins of society. Interestingly, their dynamic is briefly inverted in "Lamster" when Jackie tries to discourage Bryan from having him break into Chuck Senior's safe out of concern for Bryan's career.
  • Fighting Irish: His introductory scene has him being involved in a bar fight with Bryan stepping in as his backup, and with a loud Irish background score to match.
  • Nice Guy: Despite his introductory scene having him start a bar fight, and despite being the black sheep of the Connerty family, Jackie is proud of what Bryan has achieved in his legal career and initially declines Bryan's job offer because he doesn't want to endanger that.
  • Safecracking: Jackie's specialty.

    Rebecca 

Rebecca Cantu

Played by: Nina Arianda
https://static.tvtropes.org/pmwiki/pub/images/embillionsem_season_4_episode_2_2142430.jpg
Most people are self-absorbed, narcissistic assholes.

Wealthy venture capitalist who becomes Axe's new girlfriend in Season 4.

  • Awesomeness by Analysis: Bobby first meets Rebecca at a pitch meeting for a new advanced robot. Rebecca (who was raised by a mechanic) immediately calls bullshit on the pitch after hearing the robot emit a hum, which tells her both that the robot has an internal combustion engine and is only metastable, neither of which make it a good investment.
  • Did Not Think This Through: She makes a deal with Taylor, thinking this is good for business and that it would smooth things over between them and Bobby. Instead it enrages Bobby and makes him turn on Rebecca. The result is that Rebecca makes a billion dollars, but loses control of her company and that the relationship between her and Bobby is destroyed.
  • Establishing Character Moment: Her Awesomeness by Analysis moment described above — also her very first scene — establishes that she has intelligence on par with Axe, shares a blue-collar background with Axe, and is tough enough to see and cut through bullshit.
  • Slasher Smile: She is capable of giving genuine, warm smiles, but when she pulls this one off (and she does it often), You. Are. Fucked!

    Catherine 

Catherine Brant

"Holy shit, guys! And yeah — guys. I’m calling all of you guys — males, females, and enbies. And I have tenure. So suck it if you don’t like it."

An Ivy League sociology professor and bestselling author. She finds a kindred spirit - and more - in Chuck while at Yale.

  • Brainy Brunette: Doctor of Sociology and very, very good at her job.
  • Foil: Of Wendy, verging on Suspiciously Similar Substitute. Both women are tall, brunette, highly educated, work in the psychology field, have deadpan senses of humor, and serve as a sexual dominant to Chuck.
  • Psychologist Teacher: Her class at Yale seems to be the opposite of Chuck's, where she forces her students to engage in dialogue and ignore the conventional rules of class.
  • Put on a Bus: Chuck confirms their relationship is over by the second half of Season 5.

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