The Wolf of Wall Street Supporting Characters – Ranked by How Depraved They Are

17 Dec 2023 | 5 MINS READ
The Wolf of Wall Street Supporting Characters – Ranked by How Depraved They Are
Yasmin Omar

Financially wealthy but morally bankrupt, the cast of The Wolf of Wall Street certainly have a lot to answer for. Here, Yasmin Omar weighs up their many misdeeds.  

Beat your chest and start that humming chant because Martin Scorsese’s true-crime, finance-bro comedy The Wolf of Wall Street (2013) celebrates its 10th anniversary this Christmas. The film has spurred much conversation since its release – is it glorifying these thieving bankers? (no); does it really need to be three hours? (yes) – but today we’re opting for a different tack. It’s time to put the morality of The Wolf of Wall Street characters to the test, and assess which ones are the most deplorable. (Of course, we’re discounting the dwarf-tossing, money-laundering Jordan Belfort, played with greasy smarm by Leonardo DiCaprio, from this exercise, since he’s clearly the real villain among his merry little band of brokers.) Sound the opening bell, the trading session has begun!  

23 Teresa Belfort 

Jordan’s first wife Teresa (Cristin Milioti) does everything right. She’s supportive of her husband: encouragingly riding with him on the bus to work for his first day on Wall Street. Even after he loses his job on Black Monday – a massive downturn in the market in October ’87 – Teresa provides for them with her hairdresser salary and, as Jordan mopes dejected around the house, buoys his spirits. He’s ready to pack in his dealing-room dreams, rifling through newspaper employment listings and considering low-level sales positions. It’s her who tells him ‘you’re not gonna be stock bwoi, ’cause you’re a stock brokah!’ and pushes him to reach out to the Investor’s Center, the first step on the ladder that leads him to the big time. When Jordan starts getting a little money selling penny stocks there, Teresa is uneasy about how it’s made, who he’s screwing over. His callous severing of ties with her (an upstanding, working-class woman) results in Jordan losing his grounding connection with reality. Justice for Teresa, frankly.   

22 The Judge 

Who else’s moral compass points due north? The Honorary Samatha Stogel, portrayed in a brief cameo by Marty’s old pal, and professional curmudgeon, Fran Lebowitz (if you haven’t watched their delightful Netflix miniseries Pretend It’s a City [2021], do yourself a favour). Towards the end of the film, as Jordan finally faces repercussions for his actions, she dispassionately lists his crimes in court and sets his bail at $10 million. Her withering, I-hate-you-and-everything-you-stand-for look before banging her gavel says it all. An icon.   

21 Agent Patrick Denham

The FBI agent assigned to Jordan’s case (a weary, seen-it-all Kyle Chandler) is a straight arrow – and that’s not just coming from us, the background check Belfort ran on him reached the same conclusion. Denham follows the letter of the law during his investigation: subpoenaing the right people, tapping the right phones. And when Jordan kinda sorta bribes Denham at a sit-down on his mega-yacht, he holds firm. No lobster tails, no champagne, no rendezvous with the swimsuit-clad girls. He doesn’t even pick up a single fun coupon (read: $100 bill) that Jordan goadingly throws at him after their shambolic meeting. Yes, ACAB, except for this guy. 

20 ‘Mad’ Max     

‘This is obscene,’ says Jordan’s father, ‘Mad’ Max Belfort (Rob Reiner) when visiting his son’s Stratton Oakmont office, where chimpanzees rollerskate by desks and orgies break out in the bathrooms (despite the multiple ‘fuck-free zone’ signs). Bar Teresa, he’s the only character who calls out Jordan’s excessive spending and drug-taking. Just because you can doesn’t mean you should spend $25,000 on a single meal, Jordy. It’s more than the money, though; it’s Jordan’s marriage. Max, Stratton’s defacto CFO, provides his son with spiritual guidance and scolds him for his casual philandering. Not that he’ll listen. The only thing going against Max is his raging temper (hence the nickname ‘Mad’ Max). Is The Equaliser (1985-1989) really good enough that missing two minutes of it should trigger foot-stamping fury?

19 Captain Ted 

Poor Captain Ted. Shea Whigham’s seafarer, who helms Belfort’s 170-foot yacht the Naomi, is an honest guy, trying to make an honest living. Despite the storm warnings, his employer pressures him into sailing from Italy to Monaco in record time so he can recuperate funds from his late aunt’s soon-to-be-seized Swiss bank account. Ted nearly dies trying. The immense tidal waves pummel the boat, pull the chopper off its perch and smash through the windscreen. It’s like Poseidon himself is digging their watery graves. Now Ted’s got a shipwreck on his record – not to mention the trauma of sinking – and for what? To save some multimillionaire what for him is pocket change? The captain’s only sin is not standing up to Jordan. But then again, that’s hard to do when he’s paying your wages.     

18 Rocco and Rocco 

The name-sharing security guards (Marcos A. Gonzalez and Chris Caldovino) who protect the Belfort estate can be accused of some minor voyeurism. Over the CCTV cameras in the nursery, they watch on as Jordan’s panty-less second wife Naomi (Margot Robbie) feels herself up to tease him. In their defence, Rocco and Rocco were on the clock when this happened, so it was their duty to observe the monitors. Equally, they could’ve averted their gaze to one of the other live feeds. Pervs!

17 Heidi and Nicole   

The pair of honey-trap blondes present at Jordan’s disastrous meeting with Agent Denham. It’s not their fault that he tried to bribe the FBI; they just happened to be there. Heidi and Nicole may or may not have licked caviar off Jordan’s balls, as he claimed, but that’s their business and has no bearing on the ranking.

16 Steve Madden 

A tricky one. Given the text of the movie, we’re going to assume that shoe designer Steve Madden (Jake Hoffman) – whose company Stratton takes public – didn’t know that Jordan and his second-in-command Donnie (Jonah Hill) illegally owned a majority share in his firm. This is corroborated by the fact that as soon as Jordan is pursued for federal crime, Steve sells his stocks. However, he did select Stratton to represent his firm, which suggests a certain ethical dubiousness. To quote Jordan himself: ‘What person of any substance would trust this bunch of jerk-offs?’

15 Chantalle

The Swiss-Slovenian wife of Jon Bernthal’s Brad (played by Katarina Cas) not only smuggles millions of dollars internationally for Jordan, she also convinces her extended family to do the same. It’s never confirmed, but we’ve got to imagine she’s getting some sort of kickback for her services. She also has an affair with Jordan’s banker (Jean Dujardin), and who can blame her when he’s that suave? 

14 Brad 

You’ve gotta be sketchy to be known as the Quaalude King of Bayside. Plus, that droopy moustache is prime douchebag. So Brad’s a drug dealer who has an unsavoury relationship with women. Calling Chantalle a ‘Swiss nitwit’ and asking a teenage client to bring his sister’s underwear to their next meeting? Yuck. And yet, he does abide by his own moral code. Brad rejects Jordan’s offer to get into business with him, and therefore swerves most of the Stratton debauchery (he still attends his friend’s bacchanalian bachelor party). Most admirable, though, is his refusal to rat out Donnie – who he loathes, by the way – when the police pick him up. Brad spends a few months in prison for contempt! That’s loyalty, right there.

13 Janet

Jordan’s assistant Janet (the appropriately named Aya Cash) is a shark. That’s how you survive as a young woman in the testosterone-swirling cesspit that is the Stratton Oakmont office. Granted, she doesn’t have much screen time. She’s mostly seen bellowing out orders and cussing out Jordan (‘Lick my twat!’). Her position here is purely based on her aiding and abetting of this toxic work environment and, by extension, its actual criminality. Janet’s there for all of it – the strippers in the dealing room, the naked marching band, the sales assistant’s head being shaved for $10,000 – and does nothing. She’s complicit.

12 Naomi Lapaglia 

The Duchess herself, Jordan’s lingerie-designer second wife, played with mettle by a 22-year-old Margot Robbie. Naomi technically didn’t do anything wrong in the eyes of the law but, like Janet, she is perfectly willing to enjoy the spoils that come with stolen money. Compare how Teresa reacts when presented with a diamond bracelet (concern, discomfort, guilt), to how Naomi does when Jordan gifts her jewellery (pure, uncomplicated elation). She knew what was going on; she was in the room when Jordan conceived the ass-covering, money-hiding Swiss-bank plan for crying out loud. Something she also knew: that Jordan was married when they first started sleeping together (the blame for which primarily lies with him as the adulterer, but she doesn’t come off totally unblemished). A big plus in the Naomi column is that she files for sole custody of the children when her husband goes down for fraud, keeping the girls away from that reprobate. Just let the woman sod Bermuda grass in peace, godammit!      

11 Aunt Emma

Naomi’s English aunt (Joanna Lumley) is a minx. We first meet her at her niece’s Bahamas wedding reception when she brushes the cocaine off Jordan’s nose and knowingly remarks, ‘Into the doughnuts, I see.’ Her laissez-faire attitude to his drug-taking is compounded when she, like Chantalle, agrees to smuggle money to Switzerland using her European passport (back in the glory days when Britain was still in the EU). The cheeky, up-for-anything Aunt Emma is willing to turn a blind eye to Jordan’s sex addiction too. She operates on free-flowing good vibes, which makes her very cool – just not all that moral.

10 Manny Riskin 

He charges $700 an hour, he scarfs back free pastries… oh yes it’s Jordan’s securities lawyer (Jon Favreau). Notwithstanding his warnings about pissing off government agencies, and later advice to cut a deal and plead guilty, Manny ultimately has a vested interest in keeping Jordan in trouble. The more dire the straits, the more money he gets. He keeps his nose clean, and isn’t quite as bad as the Strattonites themselves, but he’s cut from the same cloth.

9 Dwayne

We’ve had Rob Reiner (When Harry Met Sally, 1989), Jon Favreau (Iron Man, 2008) and in The Wolf of Wall Street’s third director-turned-actor role is Spike Jonze (Her, 2013). He features as Dwayne, the grubby-looking guy behind Long Island’s Investor’s Center, where Jordan winds up pushing pink sheets at the beginning of the film. His is a business of exploitation, tricking ‘schmucks’ (his word!) who see his ads in soft-porn mags into parting with their hard-earned cash by telling them they can ‘get rich quick’. Also, the Investor’s Center isn’t regulated by the Securities and Exchange Commission, a no-no legally speaking. Dwayne is unbothered. So long as he can keep swindling postmen he’s happy.  

8 Kimmie Belzer 

Scorsese introduces just one female broker in Wolf and it’s Kimmie (Stephanie Kurtzuba), the loudmouth in the powder-pink Armani suit. One of Stratton’s original 20, she gets into banking for a seemingly selfless reason: wanting to provide for her child. As Jordan tells it, he hired her when she was desperate – three months behind on her rent and asking for a $5,000 advance to pay her son’s tuition (what he doesn’t say is that recruiting her flatters his own god complex). Any nobility Kimmie once had has all but subsided by the time we meet her. Her holiday homes and brand-new Mercedes are paid for with stolen cash. The exact details of her involvement in the company’s crime are unclear, however we do see her resisting arrest at the end, as the Lemonheads’ ‘Mrs Robinson’ cover plays on the soundtrack. The FBI really said ‘we’d like to know a little bit about you for our files’.

7 Jean Jacques Saurel

Jean Dujardin’s franglais-spouting Swiss banker knows Jordan and crew are wrong’uns before he even lays eyes on them. How? He pulls strings with the police to stop Jordan going to prison for assaulting a stewardess on the flight over to Geneva. Jean Jacques continues to bend the law by advising the Strattonites on how to hide their money through his nation’s more robust bank secrecy. His on-screen antics scratch the surface of his misdeeds, since he eventually gets arrested in Miami for money laundering through offshore boat racing. Tant pis!    

6 Sea Otter 

Final stretch now: here come the Strattonites. We’re splitting hairs. They’re all rabid venture capitalists who would screw over their own mothers to make a buck or two. Former weed dealer Alden Kupferberg (Henry Zebrowski) aka the Sea Otter – nope, the nickname is never explained – polls the best because he’s so brainless his colleagues have to be taking advantage of him up to a certain point. This is a man who didn’t graduate high school and thinks all nuns are lesbians.

5 Pinhead   

Slightly ahead of Sea Otter is Robbie ‘Pinhead’ Feinberg (Brian Sacca) for much the same reason. He took five years to finish high school and is flummoxed by a Moby Dick reference. It’s also worth noting that Robbie’s the first person arrested when the FBI raids the Stratton dealing room. That’s not nothing.

4 Chester Ming 

Another old friend of Jordan’s, who sold tyres and hash until his buddy legitimised him with a job at Stratton. Like Sea Otter and Pinhead, Chester (Kenneth Choi) comes across as a bit of an idiot. He’s not even that good at sales, notably failing Jordan’s ‘sell me this pen’ test, therefore he’s got to be fiddling the books to make his millions.

3 Rugrat 

A little knowledge is a dangerous thing, and PJ Byrne’s Nicky Koskoff – whose very obvious hairpiece earned him the moniker Rugrat – went to law school, making him easily the most booksmart of the Stratton staff. What separates him from his swindling brethren is that Nicky actually wishes ill on people. He’s shown rejoicing on a call, full-on beaming and fist-pumping, when a client reveals that a wealthy relative has died. Nicky is also a key player in the stomach-churning meeting when Jordan and his senior vice-presidents discuss how best to throw a dwarf at a target (it’s him who suggests they don’t consider these entertainers people to avoid a lawsuit??). It’s pretty inhumane stuff. 

2 Mark Hanna

The man who starts it all, who lights the fuse that sets off Jordan’s bottomless greed. The lunch scene with Mark Hanna (Matthew McConaughey), where he shows a 22-year-old Jordan the ropes on his first day on Wall Street, is arguably the most important in the whole movie. He sets the tone for everything that comes next, a false prophet instructing Jordan on how to navigate this business (‘Fuck the clients! Name of the game? Move the money from your client’s pocket into your pocket’). Hanna’s influence is felt throughout The Wolf of Wall Street. Later on, Jordan asks a waitress on his yacht to bring him a Bloody Mary every seven minutes… just as Hanna does with martinis in this sequence. He straight-up ‘prescribes’ cocaine use as a necessity for success in banking, and even does a bump at the table before they’ve ordered their food. If, like Hanna, you’re thinking about money while masturbating in a public bathroom, you’re a scumbag, no two ways about it.  

1 ‘Diamond’ Donnie Azoff 

It’s no coincidence that Jordan’s right-hand man (played by Jonah Hill) is the most corrupt – he’s the closest to him, and is therefore drawn into the black hole of Belfort’s debauchery. All the Strattonites are mercenary, that’s a given, but quitting your job selling children’s furniture mere minutes after seeing Jordan’s monthly payslip for $72,000 – as Donnie does – is a cut above. His rap sheet is extensive: he smuggles ludes onto an aircraft, exposes himself in front of Naomi, eats a live goldfish, secures the Steve Madden IPO and owns a majority share in the business with Jordan…

We must also cite the deplorable way he treats Brad, who is doing him a favour by encouraging Chantalle to transport Donnie’s money to Switzerland. He insults him and his wife, and draws attention to his illicit briefcase-giving transaction with Brad in a car park by pretending to be off his face on drugs (which, as previously discussed, leads to the latter’s arrest). Donnie’s come-to-Jesus moment when he thinks he’s going to die aboard the Naomi – ‘I did a lot of bad shit, I’m going to hell!’ – doesn’t lead him to clean up his act when he’s back on dry land; he’s still the slippery stockbroker whose lies flow like cash. He also married his first cousin. Not technically a crime, but it should be.

Yasmin Omar