Hollywood’s poker queen

She was a 26-year old cocktail waitress who ran private poker games for Leonardo DiCaprio and his A-list crowd. Then the mafia and the FBI came calling

It is only a brief glance, a quizzical tilt of the head, but it happens mid-conversation, as if Molly Bloom has scented something in the air. We are sitting in a private members’ club in New York, discussing how she masterminded Hollywood’s most glamorous high-stakes poker games, with movie A-listers, captains of industry and Wall Street titans, when Bloom glances up. She smiles at the smart guys a few feet away, getting ready to leave.

It reminds me of a moment in her memoir, Molly’s Game, in which she describes how she used to lure some of the world’s most powerful men to her games. She describes a sleek operation of schmoozing and non-sexual seduction, until they’re sitting in penthouse rooms in swish hotels, where they win and lose millions of dollars in one go.

Bloom, 36, is now “completely broke” after the authorities confiscated her poker-based profits. Not that she looks broke. Her long brown hair and make-up are both glossy and perfect; she is slim and beautiful. But the tight, fitted black and white dress by Narciso Rodriguez and YSL heels predate the dramatic downfall that made American front pages and turned her into an obsession in the tabloid weeklies. Her other clothes are from the online hire service Rent the Runway. “I went from Prada to nada,” she says.

Bloom was 26 when a man she calls Reardon in the book (many of the names in the memoir are pseudonyms, to avoid legal action) employed her as a waitress, then his assistant, then handpicked her to oversee a new high-stakes poker game he was planning. At that first game, the buy-in (the minimum number of chips that must be bought for a player to become involved in a game) would be $10,000. The location would be the Viper Room, the club inhabited by Hollywood’s young elite, made infamous when River Phoenix died there in 1993. The men at the table would include Tobey Maguire and Leonardo DiCaprio.

She was “incredibly nervous”, she tells me. “I’d watched Leonardo DiCaprio in Titanic when I was 13. Tobey was Spider-Man, a big star. I was totally seduced by it all. It was intimidating, exhilarating. So much money was changing hands. The energy was unbelievable.

“Leo wouldn’t get involved in too many hands. He wore earphones. Tobey was paying for him to be there. Leo was the bait. If Leo lost, he didn’t have to cover his losses. If he won, he got a percentage of that.”

That first night, Bloom served drinks and learnt never to speak to a player when they were engaged in a hand. The men talked to each other “about their marriages, lives, women, relationships. Tobey told stories about growing up so poor, he saw rats scurrying among the floorboards. I knew about the movies they were planning to do before anyone else; I knew when their wives were pregnant before anyone else. I had an education no woman wants. I was a fly on the wall in an all-boys’ club.”

At the end of that first game Bloom had $3,000 in tips, and was swept away by the glamour and power enveloping her. She bought sexy, smart dresses from Barneys – a Dolce & Gabbana, a Valentino – for the next games.

“I never wanted to be an actress, or a Hollywood wife,” she says. “I knew if I was smart, I could get ahead. I wanted power. By having these celebrities at my games, by having every one of those seats occupied by someone notable, I felt important.” There are other famous Hollywood stars she hasn’t named, she says, to “protect their marriages and careers. I’ll take those secrets to the grave.”

The game quickly gained a reputation as the best in Los Angeles, and Reardon eventually gave sole control to Bloom. The game she subsequently crafted was “about escapism”, and hosted not in the Viper Room but in swanky hotels such as the Peninsula and Beverly Hills, with charcuterie, cheese plates, fresh-cut flowers, two masseuses on hand, single-malt Scotch, caviar and champagne. She even booked acupuncturists for the men at the table.

Bloom now knew poker. “I watched the guys play, watched them lie to each other, learnt their strengths, weaknesses and their tells.” There was no flirtation. “I kept all those boundaries very clear,” says Bloom. She slept with two BlackBerries on her chest: one for poker, one for everything else.

“I was being socialised by men who placed money and career first and love and relationships second. These were my role models.” Marriage and children were distant prospects. “I was completely invigorated by this weird, surreal world I’d created. I felt I was doing this thing no one else was doing, and doing it very well.”

One year, she earned $4 million. She hired a trainer, got facials, manicures, bought more expensive clothes. “When you make a ton of money, there is lot of wish fulfilment that comes with being able to buy all those clothes you see in magazines.”

But her family, while close, never approved of the way she made a living. Her father Larry, a clinical psychologist based in Loveland, Colorado, mercilessly pushed his three children (Bloom has two brothers) to succeed academically and athletically. She recalls her father screaming at her and her brothers “like a banshee” when they tried to catch up with him riding their bicycles up an 11,000ft mountain. Despite suffering from scoliosis, Bloom made the US skiing team.

“My family always loved me, but that wasn’t enough for me. I think I replaced parental approval with approval from the players. I got very good at leaving home and not looking back.”

Bloom would spend “hours and hours” on the phone to Tobey Maguire. “He would text me relentlessly during games to ask me who was winning what. In the beginning, he saw how committed I was to building the game; that was his desire, too. I was a great figurehead for him. He could make decisions in the background and could ask me to institute them.”

But gradually he became more controlling. The first sign that Maguire would be tricky came when he told Bloom he wanted to be paid a fee for loaning to the game his $17,000 Shuffle Master, a machine that is supposed to deliver a fair, random shuffle every time. Bloom thought he had to be joking: “This was a Hollywood actor getting $20 million a movie,” she says. He also told her he wanted to know who was playing every week; if there was someone new, he wanted to know in advance.

“At the beginning Tobey seemed so, so nice, but it became evident very quickly there was this almost diabolical side to him,” she says.

Maguire wanted to increase the buy-in to $50,000. Then, one day, Ben Affleck called. “I hear you’ve got quite the game,” Affleck said to Bloom, who worried he’d bolt after she told him about the $50,000 buy-in, but the large sum reeled him in.

Bloom came to understand that gambling was compulsive, “and gamblers continually want to raise the stakes”. Her heart lurched when Affleck turned up at his first game, only to be asked by Rick Salomon, Pamela Anderson’s soon to be ex-husband, “Hey, yo, did that Jennifer Lopez’s ass have cellulite on it, or was it nice?” “It was nice,” Affleck said, and the game continued.

Bloom would drop cheques round to Affleck and his wife Jennifer Garner’s home. “He spoke very kindly about his wife and kids,” says Bloom. (Affleck has recently been in the news for counting cards – not in itself an illegal practice – and allegedly being ejected from casinos. “He’s totally decent,” insists Bloom. “A good guy.”)

From the men, Bloom learnt how to assert herself, to “take calculated risks. There are so many poker metaphors for life.” No women ever contacted her to play. “Women would make great poker players, but my thinking is they wouldn’t feel comfortable with playing for that amount of money. They have to take care of households, and I reckon would think what they could spend that money on.”

Bloom herself says she “was up against a lot of barriers to entry because I was a woman. No one wanted to trust me with this game or money in the beginning. I really had to prove my worth.” It’s important for a woman to retain her femininity in such a world, she argues. “If you become super-masculine, men find it more threatening.”

Men, she says, take their losses personally; she often counselled them to be more analytical and measured, rather than aggressive, if a player ran up a debt.

The first sign of trouble with Bloom’s Hollywood game came in 2008, when her bank told her it didn’t want her “kind of business” and closed her account. Maguire, meanwhile, had hit a temporary losing streak, and taken to criticising how much Bloom was making.

One night, Maguire, in front of all the players, ordered Bloom to “bark like a seal who wants a fish” to be given a $1,000 chip. She tried to laugh it off, but he repeated his demand. She was embarrassed and shocked.

“I made sure I ran every detail of every game by him,” she writes, “changed the stakes for him, structured tournaments around him, had memorised every ingredient in every vegan dish in town for him. He had won millions of dollars at my table and I had catered to his every need along the way – and now he seemed to want to humiliate me.”

Bloom refused, but felt, she tells me, “absolutely humiliated, so uncomfortable. I remember thinking, ‘How do I end this? Maybe I should do what he’s asking.’ But I had my dignity.”

Maguire, she says, “had created a scenario where he had absolute power. Life was moving so fast, I didn’t know how to fix it. One thing I learnt was people with a lot of money are miserable; their lives are empty. In one way, it’s liberating not having money. You don’t have to spend your life chasing the impossibility of that status.”

Maguire was “visibly angry” that Bloom did not capitulate. The only reason the game was still running, says Bloom, is that she had searched for the right kind of players from whom Maguire could win money. Bloom let Maguire win a bet about who would secure the Democratic nomination for president between Barack Obama and Hillary Clinton, thinking it would ensure an extended future for them. But it was for naught: one of the players took control of the game from her. Maguire called gleefully to tell her, “You’re f***ed.”

She says that men like Maguire are “very different” at the poker table; away from it she has no doubt he was “a committed and loving family man”.

Four years after masterminding the game, Bloom left LA in 2008. She was “devastated”. Why didn’t she give up and go home? “You have to understand,” she says sharply, “that this was the thing I’d done in my life that gave me self-worth and salvation.”

In New York, Bloom began again. She recalls hands of $4 million being played by Wall Street titans; her players included Helly Nahmad (who would later be jailed for his part in the ring), son of the billionaire art dealer David Nahmad.

But Bloom started to accrue problems, most seriously when she was approached by the mafia. Soon after the meeting, at which protection money was demanded, she was badly beaten by an intruder she suspects was employed by them.

“You still think you can call the shots,” he said to Bloom, as he slammed her head into the wall and punched her. He forced a gun down her throat and took thousands of dollars from her safe. When he told her they knew her family lived in Colorado, she realised she could tell no one about what had happened, and didn’t go to hospital. She stayed at home, waiting for the bruises to heal.

“It was horrible,” she says. “I don’t think it’s possible to look at the world the same after something like that happens. I thought that was going to end my life. What was so sad was that I was so out of touch with reality, and the things that mattered, that I didn’t walk away. Power and greed were my gods, and I lost myself.”

Next, one of Bloom’s LA players was indicted by the federal government; his fund had allegedly been a Ponzi scheme, and he had revealed all about Bloom’s poker games. Bloom was required to give evidence. She did so, then returned to New York to – she hoped – rebuild her empire, then exit the poker world gracefully.

But in March 2011 20 FBI agents invaded a game she had organised in New York, although she wasn’t there. Bloom hurried home to Colorado, only to find that her assets had been seized by the government and every bank account statement read that she was $9,999,999 in the red. The US district attorney’s office wanted to talk to her about organised crime.

Her lawyer insisted that the poker games had not violated any laws, but the press dubbed her the “poker princess” and “the Madam of Poker”. Bloom always thought she was operating in a “grey area”, and that – at worst – the tax authorities would give her accounts an extremely rigorous audit.

Then, early one morning in April 2013, the FBI came knocking, a frantic blur of flashlights, assault weapons, handcuffs; a moment Bloom “never in a million years” imagined happening. She was arrested and placed in a cell for 12 hours, then charged with profiting from hosting illegal poker games. She first pleaded not guilty, then accepted the charges in December 2013.

In May, she was sentenced to one year’s probation and fined $125,000.

“I broke the law and, ultimately, I didn’t have to go to jail,” she says. “That was a huge blessing.” At the end of the book, there is a simply written mea culpa: “I was brave, and I went big. I was also reckless and selfish. I got lost along the way. I abandoned the things that mattered and traded them for wealth and status.”

She insists she was “always honourable in business, but made reckless decisions. I’m a good person.”

Bloom moved back to Colorado two years ago, wrote the book, and – full circle time – is meeting Hollywood screenwriters and directors keen to make her life into a movie.

She misses the game-creating and strategising, but not the “inherent darkness” of the poker world. “I thought I could keep it light and airy, but I couldn’t. There’s a savagery to it, a preying on people. I tried to find people who weren’t great at poker to sit at a table and lose lots of money. Anybody who’s losing that amount of money has a life that is coming undone: it’s part of a bigger problem.”

Her story, Bloom says, is bigger than surviving Maguire’s ire and overseeing the poker-playing of DiCaprio and Affleck. “This was about being a woman in a man’s world, and standing up to bullies.” The seed of who Bloom was is still there – she cannot imagine “not looking at someone as a potential poker player” – but she is “petrified” of reverting to who she was. “There is such an emptiness and self-loathing there,” she says.

Bloom last saw Maguire at an event at the Museum of Modern Art in Los Angeles a couple of months ago. “We didn’t say hi, ” she says, laughing. “Tobey knows there are a lot of things I haven’t written about in this book.” What would she say to him if she saw him right now, I ask. “Come play,” says Bloom, with a mischievous smile.

BOOK EXTRACT

‘It was incredibly surreal. I was standing in the corner of the Viper Room with Leo and Tobey, counting $100,000 in cash’

Molly Bloom organises her first poker game in Los Angeles

Late afternoon on a Friday, I was shuffling around the office trying to get my work done quickly so I could leave early. I had a date with one of the bartenders at one of the clubs where I also worked.

“GET IN HERE!” Reardon yelled.

I braced myself. He was doing the thing where he filled a yellow notepad with crazy doodles, something he did when he had a new idea.

“We’re going to do a poker game at the Viper Room,” he said. “It’ll be Tuesday night, you will help run it.

“Take down these names and numbers and invite them. Tuesday at seven,” he barked.

“Tell them to bring ten grand cash for the first buy-in. The blinds are fifty/one hundred.”

I was scribbling furiously. I didn’t understand anything he was saying, but I would try to decipher his words on my own before I dared to ask a question.

He started scrolling through his phone and calling out names and numbers.

“Tobey Maguire …”

“Leonardo DiCaprio …”

“Todd Phillips …”

My eyes widened as the list went on.

“AND DON’T F***ING TELL ANYBODY.”

“I won’t,” I promised him.

When I got home I googled the words or phrases Reardon had used when instructing me to send out invites to the players. For instance he told me to tell the guys that the “blinds would be fifty/one hundred”. A blind, I found out, is a forced bet to start the action of a game. They are always the responsibility of the player to the left of the dealer.

Armed with a little understanding, I started to compose a text.

Hi, Tobey, my name is Molly. Nice to meet you.

LOSER! I thought. Scratch the “nice to meet you”.

I will be running the poker game on Tuesday. Start time will be 7 pm, please bring 10k cash.

Too bossy?

The buy-in is 10k, all the players will bring cash.

Too passive.

The blinds are …

Stop overthinking, Molly. These are just people. I composed a simple text and pressed send. I forced myself into the shower to get ready for my date. I dried off, eyeing my phone across the room the whole time.

Finally I couldn’t take it any more. I raced over and picked it up. Every single person I had texted had personally responded.

I’m in.

I’m in.

I’m in.

I’m in …

A delicious chill ran through my body, and suddenly my date with the bartender seemed very uninteresting.

On game day, I ran around doing errands for Reardon and the company, finding time in between to pick up a cheese plate and some other snacks.

The players texted me, almost compulsively, throughout the day. They wanted constant updates on who was confirmed. I felt giddy every time my phone lit up. It was like getting a text message from a boy you really liked, but even better. Reardon kept me late in the office to work on some closing documents for a new development project.

I raced to the Viper Room with some mix tapes and a cheese plate. I tried to light some candles and place a few flower arrangements around the room to make it look more inviting, but it doesn’t get much seedier than the basement of the Viper Room.

At 6.45pm I stood by the front door and waited. I fidgeted with my dress. I started to feel insecure about how to greet the players. I knew their names, but did that mean that I should introduce myself?

The first person to arrive was Todd Phillips, the writer and director ofOld School and the Hangover franchise.

“Hello,” I said, warmly reaching out my hand. “I’m Molly Bloom.” I gave him a genuine smile.

“Hi, gorgeous, I’m Todd Phillips, nice to meet you in person.

“Do I give the buy-in to you?” he asked.

“Sure,” I said, eyeing the giant stack of hundred-dollar bills.

“Can I get you a drink?” I asked.

He ordered a Diet Coke. I went behind the bar and set the enormous amount of money down.

After I served him his drink, I started counting the stack. It was $10,000 all right.

I put it in the cash register with Todd’s name on it. I felt cool, edgy and dangerous counting that much money.

Reardon came blasting in with his typical “Oh yeah!” greeting. The rumpled film producer Houston Curtis showed up next, followed by Tobey and Leo. I straightened my shoulders and smiled as naturally as I could. They are just people, I told myself. When I shook Leo’s hand and he gave me a crooked smile from under his hat, my heart raced a little faster. Tobey was cute, too, and he seemed very friendly. Steve Brill and Dylan Sellers, two major Hollywood directors, showed up next.

The energy in the room was palpable. Reardon finished ripping into a sandwich and shouted to no one in particular, but everyone in general, “Let’s play.”

It was all incredibly surreal. I was standing in the corner of the Viper Room counting ONE HUNDRED THOUSAND DOLLARS IN CASH! I felt like Alice in Wonderland tumbling down the rabbit hole.

With the exception of a few drink orders, no one spoke to me during the game at all, and I had time to watch closely. The ten men seated around the table were speaking openly. The movie stars and directors spoke about Hollywood; Reardon and real estate magnate Bob Safai analysed the market. I felt like a fly on the wall in a top-secret, masters-of-the-universe club.

At the end of the night, Reardon said, “Make sure you tip Molly if you want to be invited to the next game.” He winked at me.

As the players filed out, they thanked me, some kissed my cheek, but they all pressed bills into my hand. When they were all gone, I sat down in a daze, and with trembling hands I counted $3,000.

But even better than the money was the knowledge that I now knew why I had come to LA. I knew why I had withstood Reardon’s temper tantrums, his constant insults, the degrading cocktail-waitress uniforms, the sleazy, ass-grabby guys.

I wanted a big life, a grand adventure, and no one was going to hand it to me. I wasn’t born with a way to get it. I was waiting for my opportunity, and somehow I knew it would come. Again I thought of Lewis Carroll’s Alice, and her saying, “I can’t go back to yesterday, because I was a different person then.”