The defense rested. Closing arguments are complete. The jury has its instructions, and deliberations are underway in the tax evasion trial of Tom Goldstein, superstar Supreme Court advocate and founder of SCOTUSblog.
Press reports indicate that Goldstein’s team mounted “a sturdy and multifaceted defense.” But will this jury find reasonable doubt in the government’s case for some or all of the sixteen counts that Goldstein faces? Highlights and commentary, below the fold.
Jurors deliberated for four hours on Thursday, February 19, and will resume on Monday, February 23. Comments follow on (1) Goldstein’s decision to testify, (2) Goldstein’s ability to comply with tax law, (3) the odds of similar criminal cases in the future, (4) the late-breaking venue defense to Goldstein’s false statement charges, and (5) what to watch as jury deliberations continue on Monday.
“I’m a loser.” On the stand, Goldstein said that he’s down more than $10 million since he began playing high-stakes poker. For 2016—the taxable year at issue in Goldstein’s sole tax evasion charge—Goldstein testified that he seriously miscalculated in reporting $2.7 million in net poker income; instead, he had a multimillion-dollar loss. By contrast, the government argued that Goldstein should’ve reported more than $5 million in poker-related income in 2016.
From a tax perspective, all of these amounts could have some (and even simultaneous) truth. Goldstein could have lost millions at poker, been obligated to report some gross gambling income without offset for unsubstantiated losses (even if real), and reported different gross amounts for different years depending on his complex staking and borrowing arrangements, as well as any subsequent payouts, payoffs, or negotiated forgiveness. Untangling these narratives asks a lot of jurors—and the cognitive load may elicit sympathy for Goldstein that cuts against a finding of willfulness.
As a counterweight, much of the pretrial narrative hinged on whether jurors would view Goldstein as “a good guy or a bad guy.” And Goldstein’s need to show his humanity and character may have motivated his decision to testify in his own defense. From this perspective, Goldstein was gambling on himself—on his personal ability to persuade—as he has done so successfully throughout his storied career.
But there’s another angle to Goldstein’s testimony about his financial straits. For someone so used to success, Goldstein’s admission of massive gambling losses may operate as a sort of admission against interest—a confession of fallability and well-intentioned failure that jurors may find credible. It’s this kind of person who plausibly could make mistakes or errors on tax returns without meeting the willfulness threshold for criminal culpability.
“He’s not a dummy.” The government’s case emphasized Goldstein’s intelligence, sophistication, and alleged prevarications in various contexts—all in support of a finding of willful intent, instead of ordinary mistakes. At closing arguments, the prosecution explained a paucity of direct evidence of tax evasion, in part, by noting that taxpayers like Goldstein “hide [their malfeasance] in the tall grass.” From this perspective, the heavy evidence of mismanagement, confusion, and bad information in Goldstein’s books and records demonstrated “a textbook tax-evasion scheme.” Goldstein was curating chaos, rather than overwhelmed by it. But Goldstein’s facts aren’t Knetsch—they’re not that sophisticated technically—and it seems possible that jurors will view the financial story more sympathetically.
Indeed, Goldstein took a populist tack on the stand, stating that he “do[es] not like dealing with taxes“—not a bad strategy for a trial in the heart of filing season. It’s reasonable to think that people specialize, and a great appellate lawyer might not be so good at family law, or drafting contracts, or doing a real estate closing. But Goldstein portrayed his interest in poker as “a weirdly intellectual thing” and “a little bit problem-solving.” That mindset tends to draw people to tax law, rather than push them away from it. Lots of laypeople develop (surprising) tax expertise in the areas that touch their lives, and jurors may question whether Goldstein really would’ve ignored the tax aspects of his gambling activities. Losing millions, of course, may have dampened Goldstein’s enthusiasm to chase down these details.
Mission creep into the morass. Consistent with conventional views of IRS audits and investigations, Goldstein’s ultimate charges are very different from the issues that incited government scrutiny. Goldstein’s criminal investigation apparently stemmed from a failure to report two foreign bank accounts—an error admitted by Goldstein’s accountants even though Goldstein disclosed the accounts to them. Before the trial, Judge Lydia Kay Griggsby also dismissed charges related to Goldstein’s alleged sham employment of four women with whom he supposedly had romantic affairs. Both sets of facts potentially could’ve supported strong criminal cases and severe civil penalties.
What’s left, however, is a lot of dense (and circumstantial) financial evidence that asks jurors to parse and interpret a bunch of complex facts. (The government did get a jury instruction on willful blindness, which helps their case.) It’s understandable how the Goldstein investigation reached this point, but it’s less clear that his prosecution represents the best use of limited resources. The government prosecutes relatively few tax crimes, and those it does prosecute should count. The bigger conversation is whether (and when) civil assessments and penalties are insufficient in addressing noncompliance among taxpayers like Goldstein.
The venue defense. Venue is a key element in Goldstein’s false statements charges, which could offer jurors a cleaner story to convict—and could bring a stiffer sentence—than the tax charges. Under recent Fourth Circuit precedent, a jury may need to find “that an element of the [false statements] crime was committed in Maryland” to sustain charges brought in the District of Maryland. The government introduced Goldstein’s IP address when e-signing mortgage documents to show his presence at home in Maryland, along with e-mails that indicate that Goldstein was “directing [his spouse’s] activity” in the state. The defense, of course, raised the fact that IP addresses and physical location frequently have only tenuous connections—both concretely for Goldstein and perhaps more generally for lawyers, who may use remote access or VPNs to protect client confidentiality and information.
What to watch. Most centrally: any patterns in the count-by-count verdict, especially across the categories of charges (tax evasion, assisting in false returns, willful failure to pay tax, and false statements on mortgage charges). For example, during Thursday’s deliberations, the jury reportedly requested (and was denied) transcripts of Goldstein’s personal testimony, testimony regarding the location where Goldstein signed mortgage documents (that is, for venue purposes), and testimony about Goldstein directing part of a payment for legal services to his personal account, which the government says wasn’t reported as income. These tea leaves may indicate that Goldstein’s credibility is key, that venue may prove exculpatory for the false statements charges, and that Goldstein’s habit of making payments outside of direct channels (see also the Tobey Maguire testimony) may provide the clearest route to conviction on any tax charges.
More broadly, the Goldstein case remains compelling because it offers windows into three substantively disparate but similarly insular and arcane worlds: elite advocacy practice, global high-stakes poker, and technical tax law. Jurors could reach their verdict as early as next week, but the systemic and structural issues raised by this criminal case will persist.
Related TaxProf Blog coverage:
- SCOTUSblog Founder Tom Goldstein Trial: Taking the Stand (Feb. 14, 2026)
- SCOTUSblog Founder Tom Goldstein Trial: Week 4 (Feb. 7, 2026)
- SCOTUSblog Founder Tom Goldstein Trial: Week 1 (Jan. 17, 2026)
