Tom Goldstein Won $51 Million Against Billionaire Heads-Up Legend Andy Beal
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Beginning in 2022, embattled lawyer and high-stakes poker player Tom Goldstein went on a heads-up run that, in under a three-year period, saw him winning $51.4 million against an unnamed opponent only identified as "the Southerner." PokerNews has learned, through review of court documents, that unnamed player was Texas billionaire Andy Beal.
Beal, America's richest banker, was already known to be a primary figure in some of the biggest, and most fabled heads-up poker matches on record. Those matches were documented in Michael Craig's 2004 classic book The Professor, the Banker, and the Suicide King: Inside the Richest Poker Game of All Time, which details Beal's seven-figure swings at the Bellagio in Las Vegas against top poker players including Phil Ivey, Doyle Brunson, Jen Harman and Howard Lederer.
Two decades later, Beal, who vowed to quit poker after his losses to "The Corporation" but quickly wound up back at the table, finds himself in the middle of another movie-ready ultra-high-stakes saga. Goldstein is currently awaiting a verdict in his high-profile federal tax fraud trial stemming from his high-stakes poker escapades from 2016 to 2023, a period where he claims to have won $88 million.
The matches against Beal were so favorable to Goldstein, and the billionaire such an enticing opponent, that Goldstein claims he retired from law in 2023 in part to continue playing poker against Beal.
Sugar Babies & "The Southerner"
The matches against Beal were first referenced in court documents that PokerNews reported on in March 2025 showing payments a single unnamed player made to Goldstein between May 2022 and May 2024 that saw Goldstein netting $51.4 million in profit.
Later, in an interview with legal analyst Jeffrey Toobin, Goldstein claimed to have won $51 million beginning in 2022 from an unnamed opponent, who Toobin identified in his New York Times Magazine story as "the Southerner." Goldstein spoke to Toobin on the condition that he not name the opponent.
Goldstein says he met the Southerner at a poker game in Costa Rica. The Times reported that Goldstein, aware of the Southerner's reputation as an "inveterate womanizer," brought four sugar-baby girlfriends with him to lure Beal into his poker orbit.
"He found this to be the most interesting thing in the world," Goldstein told the Times. "That was on purpose."
Before long, Goldstein and the Southerner were playing for millions in heads-up matches, so frequently that Goldstein rented an apartment in the Southerner's city. Most of the matches went Goldstein's way, with the Times reporting that he won "roughly $50 million from the Southerner, netting $15 million for himself after paying off his investors."
Winning $51.4 Million From a Heads-Up Legend
Beal's identity as the Southerner was revealed in a Jan. 28 joint stipulation of fact signed by both Goldstein and prosecutors, which was reviewed by PokerNews, that lists Goldstein's poker wins and losses to "Andrew Beal" over a two-year period. Those transactions, including the dates and dollar-amounts, match up with previous court documents outlining Goldstein's $51 million victory against an unnamed opponent.
From May 2022 to May 2024, Goldstein won $65.3 million from Beal and lost $13.8 million for a net win of $51.4 million.
Their first match appears to have taken place around May 24, 2022, when Goldstein received a payment of $15 million. Goldstein lost $5 million the next month and took July off before winning around $3 million back in August.
After another month off, Goldstein started October by winning and then losing $6.8 million, but this is where things turned around for the superstar attorney. Over the next 19 months, Goldstein would rack up more than a half-dozen heads-up wins that included an $8.3 million win in November 2022, a $7.5 million win in February 2023, and a $9.3 million win in May 2024.
- Tom Goldstein's Winnings Against Andy Beal (2022-2024): $65.3 million
- Tom Goldstein's Losses Against Andy Beal (2022-2024): $13.8 million
- Tom Goldstein's Net Result Against Andy Beal (2022-2024): $51.4 million
Goldstein's matches against Beal are further referenced in a separate joint stipulation of fact outlining a staking arrangement between Goldstein and Michael McGuinness, who Goldstein paid $500,000 to in October 2022 for his "piece of Mr. Goldstein's winnings from poker matches against Andrew Beal."
Goldstein's run against Beal took place well after he knew he was being investigated by the feds. In October 2020, IRS agents visited his law office in Washington, D.C. in regards to the tax investigation. He was formally charged by the US Department of Justice in January 2025.
No Hard Feelings
The acclaimed show The Wire, which, like Goldstein's trial, is set in Maryland, popularized the phrase "the game is the game," a way of expressing that business, political and legal matters are never personal. The expression seems to be an apt description of Goldstein's dealings with Beal, who, two years prior to playing heads-up for millions, he threatened with legal action.
The potential suit was in response to a December 2019 poker match between Beal and Spider-Man star Tobey Maguire, who won over $15.6 million from the billionaire. Of that, Beal owed $7.8 million to the A-list actor and "refused to pay the full amount owed to Mr. Maguire following the match," according to a Jan. 28 joint stipulation of fact reviewed by PokerNews that was signed by Goldstein and prosecutors.
Maguire, who testified during Goldstein's trial, hired Goldstein to help recover the debt, and in an August 2020 email Goldstein "referenced the possibility of Mr. Maguire filing a lawsuit to secure full payment of the debt."
As a result of Goldstein's legal work, Beal agreed to pay the debt and sent Maguire $7.8 million in June 2021, which Goldstein earned a $500,000 legal fee for. Less than a year later, in May 2022, Beal and Goldstein began their heads-up matches.
There were no hard feelings between the lawyer and billionaire. The New York Times Magazine reported that Goldstein and the Southerner "struck up a friendship as well as a poker rivalry" after playing in Costa Rica and that Goldstein even hoped to make a living playing Beal as he retired from law in 2023.
"I was beating him. And that was just a way more interesting life," Goldstein said about why he retired from law, adding that playing Beal "is a way I can make a quarter-billion dollars for the rest of my life."
Goldstein's $51.6 million victory over Beal is separate from a $50 million run he went on in 2016 against billionaire Alec Gores and two Asian gamblers known as "Tango" and "Chairman." For those matches, Goldstein was coached by poker pros Andrew Robl and Keith Gipson, both of whom testified at Goldstein's trial.
Goldstein told jurors he is down around $10 million overall in poker, mostly from ring-game losses.
Jury deliberations in the federal trial, which is taking place in Greenbelt, Maryland, began on Feb. 19 and could wrap up this week. Goldstein has pleaded not guilty to all 16 charges, which include tax evasion and making false statements to mortgage lenders.
PokerNews' Chad Holloway interviewed Michael Craig last year about his book detailing Beal's heads-up matches in Las Vegas against "The Corporation."
