Ponzi Mastermind Who Lost Clients’ Millions in Hollywood Poker Breaks Silence: New Details Inside Games Played By Tobey Maguire, Ben Affleck and Matt Damon

Poker Settlement
Tobey Maguire, others reach agreement in high-stakes scandal.
A powerful man like Bradley Ruderman rarely answered his office phone. But on this occasion, the multi-millionaire hedge fund manager picked up. Just as well. When the caller identified himself, Ruderman was taken aback. It was Tobey Maguire. The Tobey Maguire.

Ruderman was used to mixing with the rich and influential; his hedge fund managed millions of dollars of other people’s money from offices in Beverly Hills. This, though, was different. Maguire was Hollywood A-list. And there was more. An intriguing invitation, extended to him: “He said, ‘Hey, we have this game … Would you like to play?'”

Spider-Man was asking him round to his house to play poker.

Now, for the first time, Celebuzz can reveal exclusively the exact details of how Ruderman — who is currently serving time in a Texas prison after being convicted of embezzling $25 million from his investors — was drawn into a clandestine world of high-stakes illegal poker games; a secret society that included Ben Affleck, Matt Damon and Leonardo DiCaprio as some of its most noted alumni.

It was a story that was to end in multi-million dollar fraud, jail and violence. One that has no heroes, but plenty of victims. Today Ruderman — a mini-Madoff — has every reason to bitterly regret taking the call that fateful day in 2006. But Maguire will almost certainly wish he never made it.


Rudeman’s tale is documented in a 206-page deposition that was conducted on March 29 at Taft Community Correctional Facility in Kern County, Calif. Celebuzz exclusively obtained the transcript of that interrogation and can now tell the full story of Hollywood’s high-roller card sharks for the first time, in Ruderman’s words.

His videotaped testimony, on oath and under the penalty of perjury, tells the explosive tale of his fall from grace, beginning in 2006 when he was still chief executive of Ruderman Capital Partners.

It was not, however, Maguire’s call that began the sad case of a man corrupted by the twinkling lights of fame and danger. That came a few weeks earlier, after Ruderman was walking along the pristine Pacific Ocean coastline in Malibu.

Ruderman, then in his early 40s, was strolling on Carbon Beach — the star-studded enclave of the rich and famous — when he bumped into a friend who was at a barbecue on the sand. It was no ordinary family barbecue. The host was Rick Salomon, otherwise known as Paris Hilton’s infamous sex-tape partner.



At the party, Ruderman got talking to a beautiful brunette. She was 33-year-old Molly Bloom, the sister of two-time Olympic skier and Philadelphia Eagles player, Jeremy Bloom.

“She asked me if I would be interested in playing in a game that they were coincidentally having the following night at that house,” Rudeman told lawyers in the deposition, “and she asked if I would be interested in participating, and I said, sure.”

Ruderman needed little convincing. “She just told me it was a traditional Texas Hold’em game … that if I enjoyed gambling and enjoyed ‘action’ that it would be worth my while to come.  I figured, you know, why not? I have nothing else to do that night and I certainly love to gamble, and it was close and it made for an easy scenario.”

He was in.

The call from Maguire, whom Ruderman had never previously met, confirmed the hedge fund manager’s place on the secret card circuit. Ruderman recalls in the deposition: “He had mentioned that he knew that I had played in a prior game that Molly had organized, and asked if I liked it, and I said yes.”

“He says, well, that’s good because we actually have a regular game that she organizes,” he continued. “It’s not on the beach, it’s in town, and here’s the facts about it and would I be interested, and I said yes.” That game, it turned out, was at Maguire’s Los Angeles house which he shares with his wife Jennifer, the daughter of Ronald Meyer, President and CEO of Universal Studios, and their two children Ruby, 5, and three-year-old Otis.



Soon Ruderman was playing regularly, usually every other week. The routine became familiar to him. Bloom invited players by text, often mentioning when stars were expected. Ruderman said in his testimony: “She [Molly] would include into your personal text message, Dave’s showing up, Tobey’s showing.”

Bloom’s games were strictly invitation-only, to venues such as the Four Seasons, the Peninsula, the Beverly Hills Hotel and the world famous Viper Room on Sunset Boulevard, a venue once owned by Johnny Depp. You had to be vetted by Bloom to get in. “You had to have pedigree,” said Ruderman.



By 2009, Ruderman told lawyers, he was well-known on the circuit as someone who paid his debts. These were no ordinary games. Secret passwords were needed to play and the door was sometimes manned by armed guards in bulletproof vests. Everything was laid on, even shoulder massages during games to relieve tension.

Ronald Richards, one of the lawyers questioning Ruderman in prison, noted: “Molly built a service business for herself by bring friendly, attractive girls to serve drinks and she provided a stable location and staff to host a game.”

Ruderman said the idea that attractive girls and drinks were the reason players showed up was wrong. “The reason people show up at the game, in all due respect to Molly, is not Molly. It’s the other players.” Like Maguire and Co., the highest-wattage members of the circle.

Bloom, it was said, could get whatever you needed. A source said illegal drugs would be part of the action. “It was known to a handful of us that one player would keep two hookers down the hall of the hotel in another room,” an insider said.

“He would disappear for 30 minutes at a time, leaving the main players in the game frustrated. In reality, he was going to do blow [in a room with] two hookers.” (There is no suggestion any of the people named in this story used drugs or hookers; indeed Celebuzz has chosen not to name the individual identified by multiple sources.)

If the extras on offer were unusual, the stakes involved were mind-blowing. In fact, there was no financial limit in the secret, unlicensed Texas Hold’em games. On one occasion, a player lost $300,000 in a night.



Maguire, 37, was a winner, however, taking as much as $1 million per-month over a period of three years, a source suggested. “That means he could have made up to $30 to $40 million from these games,” another said.

Ruderman agreed. “Tobey Maguire is the best player and a winner,” he confessed to FBI agents Jeremy Tarwater and Steve Goldman in a separate, earlier interview, according to transcripts provided to a Los Angeles court and obtained by Celebuzz.

Asked about the pot, Ruderman said in his most recent testimony: “If there are eight people playing and eight people have $50,000 in chips in front of them, that there’s $400,000 potentially that’s at risk at any moment because it’s a no-limit game.

“I believe the highest pot I ever saw, which I was not in the hand at that time, was $950,000.”



Every game, players would show up and buy in, usually for $50,000, according to Ruderman. Bloom was on hand to take the money – and her cut.

“If I lost my initial $50,000 and wanted to buy in for another $50,000, she’d hand me $50,000 in chips, and I would be in for $100,000 that night,” he said. “And she would keep track of that for every player, and at the end of the night, less expenses, she would have an accounting of who owed what to whom.”

Bloom would pocket around $6,400 per-night, Ruderman said, but she was not the house, merely a clearing agent. The next she would arrange for an assistant to pick up any money owed and deliver money won.

“She would sit in close proximity to the table with a computer typing in all the various notations,” Ruderman explained.

“If you were a loser, you knew that you had lost, and you knew that in the next couple of days she would be in contact with you to write a check in an amount or amounts to the various winners of that game. And usually what would happen is you couldn’t play in the next game until you made good on your debts for the prior game.”


Ruderman and Bloom’s A-list clientele preferred private games. Why? “It’s the convenience factor of playing in a controlled environment with a stable group of people where you don’t have to go into a casino, and you don’t have to subject yourself to, A, getting to a casino, and, B, dealing with all the riffraff that’s at a casino,” Ruderman explained. “It’s easy. It’s user friendly and that’s why I played.  And, you know, on top of the fact that I was hooked.”

The atmosphere was undoubtedly heady and adrenalin-laden, but there was one big problem for Brad Ruderman: He was a poor player. As Academy Award-winner Damon says at the start of the 1998 poker movie Rounders: “Listen, here’s the thing: If you can’t spot the sucker in your first half hour at the table, then you are the sucker.”



Unsurprisingly, others were delighted to have Ruderman play. “He was easy to take advantage of,” said one of the game’s big winners. “Ruderman was one of the biggest losers in the game. For the core group of players, having someone with deep pockets and no poker skills was a dream come true.”

Ruderman eventually accepted that he was indeed the sucker. As his losses spiraled out of control, he stole more than $5.2 million from his clients to pay off his card carousing debts. He told the FBI that Bloom preyed on him because he was “not a good gambler.” Bloom “was very aggressive to get me to keep playing,” Ruderman said in a 2009 interview.

He was clearly addicted to gambling and prepared to do anything to satisfy his craving. “I was a loser,” Ruderman said in the deposition. “I’m thinking like any gambler is thinking or any pathological gambler is thinking. You’re not keeping track of the actual numbers. You’re thinking, I’m that much closer to going on the big run. That’s the juice.”

In his testimony, he confessed: “I traded securities every single day. I tried to make clients money. As it turned out, I didn’t do it every well and I misrepresented those performances figures to my clients.”

“You would just literally take client money and take it out of the fund?” he was asked.

“That’s why I’m here [in jail] today.”

Ruderman was constantly pressed the legality of the games during his testimony. It was a crucial question, one that was to provide an unusual twist as the story played out.

Q: “I’m just trying to establish a real obvious fact. Tobey Maguire didn’t think he was breaking any laws playing poker with Brad Ruderman. Right?”

A: “I can’t surmise what Tobey knew, but I wouldn’t presume that, no.”

Q: “I mean, you guys didn’t hide — you’re playing at the Beverly Hills Hotel and the Four Seasons. Right?”

A: “Correct.”

Ruderman recalled players discussing whether the games were legal. Did they consult a lawyer, he was asked.

“No. I never did… everybody plays cards at homes.  Playing cards at home is not illegal.  It happens all the time.  It’s okay to do that…” he said.

“What made this different was the fact that we had Molly Bloom and she was performing a function that was, shall we say, unusual for a typical home poker game,” he continued. “And so many of us at the table one night, I vividly remember this, were discussing that very fact like, Hey, you know, she’s taking a piece of the action, and what’s her role here?”

Some people were invited, but rebuffed the group. “There were people that didn’t want to play in this game because they were concerned about that.”

He was instructed to name names.

“I’d rather not say, but they’re very, very prominent people,” said Ruderman.

“I’m going to request that you answer the question,” a lawyer said.

He finally relented. “Was this person’s name brought up at the table?” a lawyer asked.

“Did I bring it up? ” he responded. “No. But was Jeffery Katzenberg’s name brought up? Yes.”

Katzenberg, CEO of DreamWorks Animation and the former chairman of The Walt Disney Studios, wasn’t the only big name name checked in the deposition. Also playing were pro player Kenny Tran, Nick Cassavetes, director of The Notebook, and billionaire businessman Alec Gores, who once tried to buy the film studio Miramax.

But by far the most intriguing is Yankees slugger Alex Rodriguez — all the more so because his spokesman has long denied this author’s reporting that the man known as A-Rod played in the high-stakes ring.

Celebuzz Single Player No Autoplay (CORE)
No changes are to be made to this player



In his testimony, Ruderman was specifically questioned by lawyers about one particular game.

“I can give you some of the names I remember,” he told the attorneys. “Kenny Tran, Alex Rodriguez.”

“The baseball player?” one lawyer asked, somewhat surprised.

“Yes,” Ruderman said.

Even though a cavalcade of stars kept joining the circuit, things were souring and the atmosphere turning ugly. By 2009, Ruderman had had enough. The game was up and the chips were down.

Once his clients discovered that their savings had been squandered, an FBI investigation into the fund’s finances revealed the shadowy world of the A-list gambling club. Ruderman surrendered to prosecutors in Los Angeles and confessed to bilking investors out of $25 million in a Ponzi scheme and using $5.2 million of that money to settle poker debts.

He was sentenced to 10 years in jail for two counts of wire fraud and two counts of investment adviser fraud and ordered to repay his investors, something he is unable to do.

That, though, was not the final paragraph in the story, just the end of a chapter.

Investors in his hedge fund – whose money Ruderman taken to pay his debts – got to thinking. If the games were unlicensed and illegal, any transactions from the games were void. Investors’ money handed to winning players like Maguire could be clawed back through civil suits.

This was an unexpected twist. Getting a fish like Ruderman to swim upstream had seemed a smart idea at the start. Now it didn’t look so clever.

As one player recounted: “The irony of it all is that the game finally found the biggest fish ever, Ruderman, and we did our best to bury him every week and win his millions. Now those who fleeced him of millions are embroiled in this lawsuit. It’s like he turned the tables on us with no skill, just sheer stupidity.”

The civil cases soon found their targets. Cassavetes, Salomon and Welcome Back, Kotter star Gabe Kaplan were also sued. Details soon started leaking out. It was said that Ruderman lost $311,300 to Maguire, including one losing hand of $110,000 in 2007. The actor countered by saying that his winnings only amounted to around $187,000 and insisted he lost nearly as much as he won.

Hollywood-watchers were gearing themselves up for the full public hearing, where all the details would come out. But it never happened. All players in the ring did the sensible thing and settled. In all, the 22 people who sued to recoup poker winnings received a total of more than $1.75 million. A slew of famous names breathed a sigh of relief. They did not have to appear in court.

That is why Ruderman’s deposition, made before the settlement, is so important in shining a light on the underground poker ring. He says he is only speaking out to help the victims of his crimes, but he knows it is not without risk.

When Ruderman surrendered to FBI agents after being charged, he was concerned players would try to kill him.

One player turned up unannounced at Ruderman’s home before he turned himself in. But Ruderman wouldn’t open the door. “Couldn’t take the chance,” he said. “I had no idea if he had any other intentions in mind. At that time, I didn’t know, you know, who wanted to do what to me.”

Others were equally fearful. After Ruderman was arrested, Bloom left him phone messages. He told lawyers: “She said, ‘Call me.  We need to talk.  I heard about what happened, and I have to talk to you.’”

Bloom herself relocated to New York that year to set up a new operation for Wall Street brokers. Russian mobsters are said to have joined in and violence ensued, during which Bloom was said to have been roughed up. Some insiders believe the gangsters wanted to intimidate Bloom before she was questioned by feds.

Hollywood’s A-list poker kings may have been spared the indignity of appearances in open court, but Ruderman, the man they regarded as a sucker, has had the last laugh.

Ruderman is no angel. He defrauded people out of millions and ruined lives. But at least he had the dignity to speak out.

As he says in his deposition: “My testimony, both on the record and off the record, is always first and foremost, with the victims in mind.  My actions, I have to take consequences for them, and whatever happens happens.  But it’s the victims that matter first.”

Late nights at Tobey Maguire’s will never be the same again.