Tom Goldstein, the SCOTUSblog co-founder and Supreme Court whisperer with over 40 arguments before the bench, was convicted of tax evasion, false returns, wire fraud, and mortgage lies in a Maryland courtroom.
After a seven-week trial, it took days of deliberation by the jury to come to a decision, but eventually they delivered the blow in a brutal reminder that when the taxman comes knocking, even the sharpest minds can get caught.
Tom Goldstein, 55, is now facing the proposition of returning to prison for some some serious time. Sentencing is pending but the maximum exposure on some counts hits decades behind bars. Appeals will almost certainly follow, but for now, this is a massive fall from the heights of legal stardom.
High-Stakes Tax Fraud Gone Wrong
This is not just another tax dodge story; it had everything. Prosecutors laid bare the insane swings and secrecy of the absolute top tier gamblers where private jets and high-stakes private cash games with pots routinely hitting seven figures are the norm. Instagram playboy Dan Bilzerian is one such character in these circles.
Goldstein supposedly pocketed millions in unreported poker profits, most glaringly and publicly a $26 million heater in 2016 against a California businessman.
He was accused of funneling money through his old law firm Goldstein & Russell to cover gambling debts, then misreported his income on tax forms while securing a $1.98 million mortgage by conveniently forgetting to mention $14 million worth of gambling debts.
Goldstein took the stand himself, admitting to messy record keeping but swearing it was all honest mistakes with no intention to defraud the government.
He also claimed to be a lifetime net loser in poker with losses of more than $10 million overall, but the government painted a very different picture in court, providing ample evidence of substantial unreported wins. The defence didn’t sway the jury at all on the core charges.
Star Witnesses Fail to Convince Jury of Tom Goldstein’s Innocence
The witness list for this trial was quite impressive, providing plenty of drama.
Molly’s Game architect Tobey Maguire testified about hiring Goldstein in 2020 to chase down a $7.8 million debt which was his half of a $15.6 million win by Goldstein against Texas billionaire whale Andy Beal, as well as paying Goldstein a $500,000 fee that prosecutors said got rerouted to cover Goldstein’s own holes.
High-stakes reg Andrew Robl detailed staking and coaching Goldstein for those brutal heads-up battles. Court documents revealed Goldstein’s run against Beal from 2022 to 2024 detailing how he won $65.3 million and lost $13.8 million for a net profit of $51.4 million.
These are numbers that make most professional’s careers look like pocket change.
For the ultra-high-stakes crowd, this judgement hits close to home. Private games with no paper trail have long been the norm, but the IRS doesn’t care about “it’s just gambling” excuses. Legit winnings are income and that’s the end of it.
As for what hope is for an appeal, this is unclear. Tom Goldstein’s legal team complained loudly about the way the government dug deep into their client’s private life to make him look as bad as possible, even on unrelated matters.
There was also an admission during the trial from Walter Deyhle of GRF CPAs & Advisors, Goldstein’s tax team, that mistakes were made by them, rather than Goldstein deliberately hiding any crime.
Goldstein said on the stand:
“The mistakes, responsibility for those tax years is mine. I may end up continuing to pay for this for a long time. That’s my responsibility. It’s just very different from whether I committed a crime.”
Prosecutors are yet to say what sentence they will seek for Tom Goldstein, but it doesn’t look good no matter how you slice it.
He faces up to five years behind bars for tax evasion but up to an eye-watering 30 years for the mortgage fraud charges, as well as some extra years for involvement in the preparation of false tax returns.
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