Did Tom Goldstein Commit Tax Fraud with Jungleman and Kevin Hart’s Money?

Tom Goldstein’s ‘Little Black Book’ of poker players contained some of the biggest celebrity names in the world. From Spider-Man actor Tobey Maguire to Jumanji star Kevin Hart, Goldstein’s poker playbook was discovered in evidence this week as his private ‘poker ledger’ became public knowledge in Maryland.

What is Tom Goldstein Accused Of?

This was the fourth week of the trial of Tom Goldstein, which is investigating the high-profile lawyer on charges of committing tax fraud. At the heart of the case, which comes following Goldstein’s indictment in January 2025, is the debate over whether Goldstein hid his indiscretions at the poker table when it came to declarations, missing out wins and losses for tax avoidance purposes.

Over the past month, the trial of Tom Goldstein has continued, documenting his many poker games with celebrities such as Tobey Maguire, Kevin Hart and others, including some of the biggest names in poker. Goldstein claims to have made $88 million playing poker in private cash games, most of which took place heads-up.. but is he lying? The amount seems vast, and while the so-called ‘poker ledger’ he kept details wins and losses that would make regular players raise their eyebrows, the amounts are nowhere near as inflated as that amount.

A $750,000 loss to Dan ‘Jungleman’ Cates is one case in point. Jungle would likely have kept coming back to the font for another glass of water were Goldstein keen to make it a regular game but no other games between the pair are detailed. Silicon Valley businessman Chamath Palihapitiya, a close personal pal of Phil Hellmuth, also beat Goldstein, taking the lawyer for $176,000 in a one-time heads-up cash game.

Goldstein Reveals Poker Ledger of Legends

During the past week in court, the infamous poker ledgers were released as evidence, with case prosecutors questioning why they hadn’t been in the public eye at the start of the trial or even pre-trial.

“After [Mr.] Goldstein chose not to provide the poker ledgers to Mr. Deyhle in 2016 and 2017, he again chose not to provide the poker ledgers to the expert witness he picked to criticize Mr. Deyhle’s and Gelman’s work,” prosecutors told the judge in the case and it is hard to disagree with their point with any validity.

Goldstein’s little black book of poker buddies includes some seriously rich and mega-famous types. The former Spider-Man star Tobey Maguire arrived in Maryland last week to give evidence that he believed the matches he played in against billionaire Andy Beal weren’t being honestly recorded.

Allegations surfaced that the money Maguire won was not being declared for tax reasons and while the Spider-Man actor is not being accused of doing anything wrong, the nature of these private cash games are highly suspicious. Who won what and where the money went afterwards is a matter of great debate, with the important point being whether money has been ‘washed’ to avoid having tax paid on it.

Which Poker Professionals Did Goldstein Lose To?

Of the many players Goldstein took on, who had the best record against him? Well, a high Stakes Poker regular and someone who ended up coaching Goldstein after they played. Andrew Robl has shared the felt with plenty of big names on PokerGO over the past few years, with Hollywood actress Jen Tilly, Finnish Poker Hall of Famer Patrik Antonius and 10-time WSOP bracelet winner Phil Ivey all coming up against him.

Robl took Goldstein for millions, eventually helping his opponent improve at the game. Goldstein did win some money playing in these games, with one particular double alvo earning him $26.4 million. Alec Gores was the lawyer’s victim in two sessions, one of which costing him $17.4 million and the other seeing him drop $9m.

Other matches took place against the DC-based WPT Champions Club member Tony Gregg, and the high stakes cash regular Bob Safai. More featured the former husband of Shannen Doherty and Pamela Anderson, Rick Salomon. Another took place against the Jumanji: Welcome to the Jungle actor Kevin Hart.

With another week or so expected in the trial of Tom Goldstein, Maryland awaits a verdict which could have ramifications for other high rollers looking to play private games, newly aware that the tax implications of wins and losses could be far reaching.