Olympic Trials to Court Trials: How Molly Bloom Became the Poker Princess
It’s not often that someone trains for the Olympics as a mogul skier, becomes the hostess of America’s highest-stakes poker games, get’s involved with the Russian mob, faces nearly a decade behind bars, and gets off practically scot-free. Unless you’re Molly Bloom, America’s poker princess and inspiration behind the best-selling book and Academy Award-nominated film “Molly’s Game.”
Here’s the incredible tale of how Molly Bloom hosted poker games with stars like Leonardo Dicaprio and survived a brutal scare at the hands of the Russian mob.
Meet the Blooms
Molly Bloom grew up in a talented family full of high achievers. Her father was a clinical psychologist and a professor at Colorado State University while her mother owned a fly fishing guide company and her own clothing line. Her two brothers were equally impressive.
One brother, Jordan, is a Harvard-educated cardiothoracic surgeon at Massachusetts General Hospital. Her other brother is Jeremy Bloom, a two-time Olympic skier, three-time World Champion, and 11-time World Cup Gold Medalist. Oh, and when Jeremy wasn’t skiing, he was excelling on the football fields at the University of Colorado. Bloom was an All-American receiver and return specialist who was drafted by the Philadelphia Eagles, making him the only athlete in history to ski at the Olympics and make an NFL team.
Naturally, Molly grew up in a hyper-competitive environment. As Ricky Bobby once said, ‘If you’re not first, you’re last.” And with that mindset, Molly would do everything in her power to succeed, excel, and get attention, and skiing would be the vehicle, at least initially, by which she would get those things she so desperately craved.
There wasn’t much to do in Loveland, Colorado, her hometown, but when winter came, everyone and their moms made the weekend trek to the slopes. A young prodigy, Molly was being groomed to be an Olympian, but at the age of 12, disaster nearly ended her promising career. Molly had scoliosis and needed surgery to correct the potentially-devastating issue.
A Miraculous Recovery
Doctors were skeptical whether she’d ever be able to bomb down the slopes again. Like you’ll soon find out, Molly wasn’t too concerned with following the rules or heeding to the advice of others, and shortly after the operation, she was back on the slopes, improbably looking better than before. With her surgically-fused spine, Bloom was on the fast track to the Olympics.
When it came time to go to college, Molly, one of the country’s top skiers, opted for a school that was both close to home and could afford her an opportunity to keep skiing at an elite level. In the fall of 1996, Molly enrolled at the University of Colorado Boulder, one of America’s best universities in terms of producing Winter Olympians.
End of a Dream
As a sophomore, Bloom bloomed, making the U.S. Ski Team while placing third overall in the country in her signature event- moguls, a discipline of freestyle skiing. As the competition began to heat up for the 1998 Winter Olympics in Nagano, Japan, Bloom took a turn for the worst, literally. In a qualifying run, Bloom took a nasty spill.
Her Olympic dreams were over, but the ramifications were much more significant than a missed spot on the team. Her body was out of commission. She had battled various injuries season after season and her back was a mess, stemming from her surgery as a child.
When One Door Closes, Another Opens
“I had a pretty horrific crash on my Olympic qualifying run,” she told NPR. “And after I quit the U.S. Ski Team, there was a fair amount of, you know, grief that follows that.” But that grief would pale in comparison to the horror Molly would face staring down the barrels of 17 assault rifles during an FBI raid on her home just a few years later.
After the crash, Molly returned to school to finish her degree, but her aspirations of attending a top-tier law school and becoming a lawyer were also over. Molly was trapped in a life she didn’t want to live, and her gut told her to head west. She packed her bags and moved to L.A.
Molly reached out to a friend in L.A. and asked if she could crash on the couch while she sorted out what was supposed to be a temporary year-long adventure. Her dad, who raised Molly in a structured environment centered around athletics and academics, wasn’t thrilled by his daughter’s decision to move across the country without a job or a plan for the future.
He decided to cut her off financially, nearly severing the fragile relationship the two had maintained over the years. With her connection to home reduced to almost nothing and no concrete plan in place, Molly opted to use her good looks to jumpstart her new life.
An attractive woman with an athletic build, Molly took up a job as a cocktail waitress at a high-end bar. She was banking on her body and jovial personality as a way to rack up tips on a nightly basis, but little did she know that in just a few years, she’d be making millions of dollars per year solely on tips.
Bloom’s shift had just finished. The exhausted waitress was meandering back to the couch she called home when she was nearly run over by a silver Mercedes. The potentially fatal misfortune actually turned into a blessing in disguise that opened the Pandora’s box of a lavish lifestyle she would soon live.
Reardon Green emerged from the Mercedes apologetic and infatuated. He was captivated by Bloom’s looks and charming personality. Their encounter was brief, but it ended with Green offering Bloom a job at his restaurant, Boulevard. Working at Boulevard wasn’t necessarily an upgrade from her first job, but it allowed Bloom to get her foot in the door with other more lucrative industries and opportunities, including underground poker.
By day, Bloom would be serving drinks in a highball glass, and by night organizing poker games full of high rollers. When Bloom’s shift at the restaurant ended, she’d head over to meet Green at the Viper Room. That’s where he hosted his weekly poker games for celebrities.
The Viper Room was a dingy nightclub on Sunset Boulevard, but it was inconspicuous and provided the perfect atmosphere for these games. The games attracted Hollywood stars, athletes, businessmen, and real estate moguls. The buy-ins were high and the stakes were higher, but something was missing. That something was an attractive piece of eye candy that could act as the game’s host and greeter, and that someone that could fill the role was Molly Bloom.
“My boss, Reardon, a real-estate investor, had decided I would be the hostess of a poker game he had organized at Hollywood’s infamous Viper Room.” Bloom told Vanity Fair. Just like that, Bloom had a new career, one she knew nothing about and one she never could have dreamed of having.
First Night on the Job
“It felt more like a sports arena than the basement of the Viper Room. Reardon finished ripping into a sandwich and shouted, ‘Let’s play’” (“Molly’s Game”). “I was standing in the corner of the Viper Room counting ONE HUNDRED THOUSAND DOLLARS IN CASH! I was in the company of movie stars, important directors, and powerful business tycoons.”
That was Bloom’s first night hosting the underground Poker games, and when it ended, she pocketed $3,000 in tips. In hindsight, that $3,000 would be a trivial amount, and with each subsequent game, the guest list grew, the stakes were raised, and the potential for trouble magnified.
“Wow, they are swinging, huh?” Rick said. “Want to [have sex]?” (“Molly’s Game”). That was Rick Salomon, the infamous star, director, and producer of the Paris Hilton Sex Tape “One Night in Paris.” Molly’s face lit up like a Christmas tree. She politely declined the offer and kept her composure. Rick paid the $50,000 buy-in and asked for $200,000 in chips.
More stars began to flood the Viper Room, and the money on the table began to reach unbelievable amounts. Rick, one of the more crass players in the game, asked Ben Affleck, a regular at Molly’s games, a rather personal question.
Business is Boomin’
“Hey, yo, did Jennifer’s ass have cellulite on it, or was it nice?” A moment of tense silence filled the room before Ben nonchalantly answered. No punches were thrown, yet. The games, and Molly’s reputation for being a fantastic host, kept on reaching new heights. Leonardo DiCaprio was becoming a familiar face. So was billionaire founder of Cirque Du Soleil Guy Laliberte. Tobey Maguire, one of the more skilled and neurotic players there, wouldn’t miss a game.
With all the new star power, the Viper Room became inadequate. Bloom had a burgeoning business — she had registered an event-planning LLC in her name — and needed a new venue to host some of the highest-stake, celebrity-laden games in the country.
Beverly Hills, That’s Where Bloom Wants to Be
So long as Bloom only kept tip money, the venture was legal (and taxable). She may have missed the Olympics and the potential to win the gold medal, but Bloom had stumbled upon a gold mine that she planned on mining to its full extent.
Following the Viper Room, Bloom began to host games at some of L.A.’s most lavish venues, such as the Peninsula hotel, the Beverly Hills Hotel, and the Four Seasons. Buy-ins increased, scantily-dressed models that acted as masseuses perused the game’s grounds, and five-star restaurants catered the festivities. Celebrities, even those not directly involved in the game, began to show up, like Nelly and the Olsen twins.
As for Bloom, her life began to look more similar to that of a Hollywood actress than an elite skier from small-town Colorado. She dated Drew McCourt, the son of former Dodgers owner Frank McCourt, partied with celebrities, and swapped out her discount heels for Louboutins and her sedan for a Bentley.
However, not all that glitters is gold, and the empire that Bloom worked so hard to build up was about to come crashing down in dramatic fashion. “Bark like a seal who wants a fish,” Tobey Maguire instructed Bloom. Bloom rejected the offer. Maguire had been growing impatient with Bloom for weeks, and now he was taking his frustrations out on her in front of her guests, her clientele, her livelihood.
Bark Like a Seal? No Deal.
Maguire, who was one of the stingiest players in the game, wanted Bloom to get on a table and demean herself for a tip. Bloom continued to refuse, but Maguire wouldn’t back down. “I’m not kidding. What’s wrong? You’re too rich now? You won’t bark for a thousand dollars? Wowwww…you must be really rich.”
Bloom was, in fact, very rich. In a single year, she pocketed over $4 million from tips alone. However, her relationship with Maguire had soured, and that spoiled relationship indicated trouble around the bend. With that in mind, Bloom packed her bags again and headed east to New York City, a poker hotspot where she intended to capitalize big-time on the Wall Street money that flowed into the games like water after a storm.
Bloom in the Big Apple
In 2009, Bloom arrived in New York City with eager eyes. There was a lot of money to be made, and she had the recipe for success. Like she had done in L.A., Bloom rented out suites in some of Manhattan’s most luxurious buildings, filled the rooms with models and gourmet food, and made an exclusive invite-only list that would generate enough hype and word of mouth to promote itself.
The buy-in was a cool $250,000 and the stakes were extraordinary. Wall Street executives, billionaire business moguls, celebrities, and the likes of New York Yankees star slugger Alex Rodriguez all made the rounds at Bloom’s weekly New York City games.
Sliding Down a Slippery Slope
But the big city lights of New York proved to be too bright, and that’s when Bloom began to unravel. “When the games started lasting more than 24 hours, my life was not sustainable,” Molly told the Denver Post. “I turned to drugs and alcohol to manage it.”
Bloom would pop pills to stay awake, use alcohol to drown her sorrows, and take Xanax to level herself off. She was caught in a vicious cycle with no end in sight. To make matters worse, Bloom started guaranteeing games and bankrolling her players with her own line of credit; a recipe for an unsustainable business model.
Taking a Rake Was a Big Mistake
“I was essentially giving them money to play. It wasn’t like, ‘Thanks for bringing me a drink’ or ‘Thanks for inviting me.’ It was like, ‘Thanks for allowing me to win $5 million with the money you vouched for,’” Bloom recounted to the LA Times.
As Shakespeare once said in Hamlet, “Neither a borrower nor a lender be; For loan oft loses both itself and friend.” Bloom wasn’t about to lose any friends by extending credit, but she was about to lose large sums of cash. After being burned by a player for a quarter of a million dollars, Bloom began taking a percentage of the pot for herself, known as a rake.
Taking a rake is illegal, and it led Molly down a slippery slope more dangerous than anything she had skied in her life. In 2010, Bloom’s personal driver introduced her to two members of the Russian mob who offered Bloom protection. That offer wasn’t so much a question as it was a proposition she shouldn’t refuse, which she did.
The mob isn’t really in the business of being denied, and when they were, they punished Bloom. “I opened my mouth to scream, and he pulled out a gun from under his jacket and slammed me back against the wall” (“Molly’s Game”). Bloom pleaded with the armed intruder, offering him money and valuables.
Down Deep in Depression
The man, not interested in her material things, kept punching her in the face. Blood was gushing from her nose. Finally the man ceased, but not before issuing her a stark warning. “Don’t disrespect us again.” The “us” the man was referring to was the Russian mob.
For days, Bloom hid in her apartment while her battered and bruised face healed up. The mob was on her case, people owed her big chunks of money, and word got out that the FBI was beginning to uncover an underground poker ring in New York. Things were not looking up for her.
In 2011, the FBI raided one of Bloom’s games. The government seized her money and froze her assets. Bloom was forced to testify against one of the locals at her games, hedge-fund manager Brad Ruderman. Ruderman was being sued by angry investors for allegedly running a Ponzi scheme and using investor money on poker games. Ruderman blew all the money ($25 million) while simultaneously managing to network at Bloom’s games and recruit more helpless investors into his scheme.
Bloom left the Ruderman ordeal broke and out of options. So she moved into her mother’s house back in Colorado and began to pen her story, hoping to get it published and earn back all of the money she had lost.
FBI Comes in Gun Blazin’
For a moment, life for Bloom appeared to be on the mend. The first draft of her book was complete and she was in negotiations for a book deal. In 2013, she moved back to L.A. and settled in an apartment in West Hollywood. That’s when the FBI showed up again, but this time with 17 automatic weapons pointed at her and a warrant for her arrest.
Bloom was escorted away in handcuffs. Bail was eventually posted, but not without a cost. Bloom’s mother was forced to sell her house in order to procure the necessary funds. Once again, Bloom appeared to have bitten off more than she could chew.
Bloom Catches a Much-Needed Break
Bloom was facing a five-year prison sentence and millions of dollars of debt. She had dug a hole she could not get herself out of. The judge offered to reduce Bloom’s sentence should she implicate more people in the poker ring. Bloom wouldn’t budge. She cared more about her reputation (whatever was left of it) and her integrity than a reduced sentence.
Seemingly out of good options, Bloom finally caught a break. In 2014, a judge ruled that Bloom “had ultimately been a minor player in the illegal gambling ring and sentenced her to one-year probation, fined her $1,000, and said she would have to perform 200 hours of community service” (LA Times).
Banking on a Book
Others sentenced in the massive underground poker ring included Russian mobsters and Hillel Nahmad, a Manhattan art dealer who owns more Picasso’s than most people own televisions. Bloom wasn’t fully in the clear. She still had no money and no clear path to financial restitution. Then Harper Collins came calling, offering her $45,000 for her book.
Bloom would not disclose any names that hadn’t already been revealed in court documents related to the Ruderman Ponzi scheme, but what she could tell was juicy and enticing. She’d been a fly on the wall at some of America’s most lavish and grandiose poker games, and the stories she had to tell came straight from a Hollywood movie script.
On to the Silver Screen
The book, “Molly’s Game: The True Story of the 26-Year-Old Woman Behind the Most Exclusive, High-Stakes Underground Poker Game in the World,” became a bestseller and spawned a movie deal. To hook the movie, Bloom had to tirelessly plead and pester Hollywood agents, connections, and lawyers to land a meeting with Aaron Sorkin, the Academy Award-winning screenwriter of the “Social Network.”
Once the two met, Aaron Sorkin knew this was a piece he’d be passionate about doing. He described Bloom as professional and poised, despite the massive debt she had and the broken reputation she carried with her at every turn.
Molly’s Game: The Film
The film, “Molly’s Game,” stars Jessica Chastain as Molly and Kevin Costner as Molly’s father. Like her book, Bloom would not disclose every name or person she interacted with and admits that there could have been much more salacious information revealed, but Bloom took it upon herself to preserve her integrity and the reputations of those at her games.
Since the movie’s release, Bloom has moved back to Colorado where she plans on living a quieter life. Despite moving away from the big city that helped quench her thirst for attention, Bloom doesn’t plan on being stagnant. Bloom plans on starting a coworking space exclusively for women.
On the Ellen DeGeneres show, Bloom gave an honest, heartfelt testimony about her life and its trials and tribulations. “I’ve been hugely successful at times in my life, and I have also been in ruins,” she said. “But the lessons I learned on the way up were just as valuable on the way down. This time I will use everything I learned to do something that matters.”
Like a phoenix rising from the ashes, Bloom’s second chance at life will not be taken for granted. She plans on using her experiences to empower women and better the lives of those around her. She’s not craving fame or money; nor is she’s chasing Olympic gold.
The Future Looks Bright
She’s at peace with her journey, content with how it all panned out. She could have died or ended up in jail for nearly a decade. Or she could have sold out many high-profile stars for a reduced sentence. She gambled on herself, on her pride and integrity, and accepted her fate, whatever it would be.
Fortunately for Bloom, her punishment wasn’t crippling. When she was down, like she had been so many times before, she knew she had to get up. She had to fight for a book deal and find a company willing to publish her story while deliberately omitting some of the most explicit and interesting details.
The Best of Bloom
After that, Bloom had to fight again to find someone to make her movie happen, a director willing to take a chance on her. She did, and Bloom seized the opportunity in every way possible. The movie was a smash hit, she’s back to making money, and she plans on empowering women. She can go to the grave proud of the way she conducted herself in trying times under the scrutiny of millions of people.
Now, the world is open to Bloom and she plans on taking full advantage of it- this time for good. This time in a way that would make her father, the one who cut her so many years ago, prouder than he could have imagined.