The trial is over. The sentence is in. The appeal has begun.

On July 24, 2026, Tom Goldstein, superstar Supreme Court advocate and founder of SCOTUSblog, was sentenced to six years in federal prison following his conviction on nine tax counts and three mortgage fraud counts.

What explains Goldstein’s sentence? What are Goldstein’s prospects on appeal? And what broader lessons does the case offer for sophisticated defendants facing criminal tax and other white-collar charges?

I asked Rachael Jones, a McKool Smith principal and former Deputy Chief of the Criminal Division at the United States Attorney’s Office for the Northern District of Texas, six questions about Goldstein’s proceedings. Her answers, below the fold.

The government sought a prison sentence of approximately eight years, while Mr. Goldstein requested a noncustodial sentence. What explains this extraordinary difference?

Ms. Jones: The disparity in the sentencing requests is not surprising. The government sought a guidelines-based sentence, while Mr. Goldstein—understandably—sought to avoid incarceration altogether. Despite his extraordinary career and professional accomplishments, Mr. Goldstein is no different from any other defendant in this fundamental respect: no one wants to go to prison.

The Judge sentenced Mr. Goldstein to six years.  Do you think the Judge might have imposed a shorter sentence if he had been more realistic in his ask for something besides a noncustodial sentence?

Ms. Jones: I am always reluctant to second-guess fellow attorneys because I lack their access to the full record and have not conducted the same in-depth analysis. He was represented by accomplished and capable counsel, and Mr. Goldstein is a sophisticated lawyer. I have no doubt they carefully evaluated and analyzed the pros and cons of all the potential arguments, and I am equally confident that Mr. Goldstein was involved in making the decision. Whether a more measured sentencing request would have yielded a lower sentence is ultimately unknowable.

I have seen defendants benefit from realistic sentencing proposals—even when those proposals are difficult for clients to accept. As a prosecutor, I occasionally heard arguments from the defense that I struggled to refute. Defendants naturally gravitate toward probation or noncustodial sentences, and the tension between client expectations and sound advocacy strategy is a recurring challenge in any punishment hearing. That said, it is the client who will be lying awake in a prison cell wondering whether things might have been different had he asked for probation.

Here, Mr. Goldstein wagered that his substantial mitigating factors—including his significant gambling disorder—would persuade the Court to grant leniency. As a former colleague from my days at the U.S. Attorney’s Office used to say, “the answer is always no, until you ask.” Mr. Goldstein asked, the Judge declined, but at least he will not be left wondering what might have been had he sought probation.

In your view, which factors carried the greatest weight in determining Mr. Goldstein’s sentence, and how did Mr. Goldstein’s background as a highly accomplished lawyer affect sentencing?

Ms. Jones: This is an instance where Mr. Goldstein’s “virtue is his vice.” He is a sophisticated, accomplished lawyer who unquestionably knew better—and it was that same sophistication that enabled him to commit and conceal his crimes over several years. The government presented evidence that he misled accountants, misused his trust account, and committed mortgage fraud. This was not a single lapse in judgment but a sustained pattern of calculated deceit. Equally damaging, the government demonstrated that Mr. Goldstein continued to disregard the tax laws even after learning he was under criminal investigation—and again after his conviction. That sophistication is tough to ignore when a Judge determines what constitutes a fair sentence. Indeed, the Judge indicated Mr. Goldstein knew better.

Was the Judge’s sentence within the range you expected?

Ms. Jones: I was not surprised. Given the sophistication of Mr. Goldstein’s crimes and their duration over several years, I expected a substantial custodial sentence. I think Judges believe sentencing in tax cases must promote respect for the law with a serious consequence. Everyone is obligated to pay taxes, yet the federal government lacks the resources to investigate and prosecute every violation. Prosecutors must strategically allocate limited resources to recover funds owed to the government and to deter future offenders. The deterrent value of a significant sentence is particularly important in high-profile cases—and this is certainly one. Mr. Goldstein cultivated a large following through his blog and was a well-known lawyer even before the blog. His conviction and sentence will inevitably reach a broader audience, reinforcing the message that sophisticated tax evasion carries serious consequences.

In denying Mr. Goldstein’s post-trial motions, the Judge recognized that some errors may have occurred but concluded that they did not prejudice the defense. Do you think there is much likelihood of Mr. Goldstein succeeding on appeal?

Ms. Jones: While I have not examined the specific issues the Court referenced, full reversals on appeal are statistically rare, and this case is unlikely to be an exception. Standards of review typically favor the district court rulings. Federal judges are accomplished jurists who arrive at trial thoroughly briefed—not only by counsel but also by their law clerks, who independently research contested issues. The pretrial motion practice in federal court ensures that judges have ample opportunity to consider contested evidentiary and procedural questions well before they become trial issues. By the time a ruling is made on the record, experienced judges have already assessed the appellate risk and crafted their reasoning accordingly.

Judge Griggsby brings over a decade of federal judicial experience—spanning the Court of Federal Claims and her current district court post—along with a distinguished educational background and prior litigation experience at a well-regarded firm. Her tenure at the Department of Justice, where she handled complex civil matters at both the trial and appellate levels, further reinforces confidence in her ability to manage a record that will withstand appellate scrutiny. On the prosecution side, DOJ often supplements trial teams with appellate specialists, and a case of this magnitude is likely to have top-notch lawyers. Those appellate liaisons review potential issues in real time and advise trial counsel on how to preserve the record and avoid reversible error. Prosecutors are institutionally risk-averse—they would rather concede a questionable point than risk a retrial. Given all these institutional safeguards and Judge Griggsby’s experience, I would be surprised if Mr. Goldstein prevails on appeal.

What broader lessons does this prosecution offer about the sentencing and appellate treatment of sophisticated defendants in criminal tax and other white-collar cases?

Ms. Jones: There are a couple of lessons from this case, though they are not particularly new or novel. First, the Department of Justice remains fully committed to prosecuting fraud in all its forms. This prosecution does not alter the established landscape for sentencing or appellate treatment—courts have long imposed substantial sentences on well-educated professionals convicted of sophisticated fraud schemes. The fact that most white-collar defendants are technically “first-time offenders” offers little protection; their crimes typically span years, involve deliberate concealment, and reflect a pattern of conduct that judges take seriously. Philanthropic contributions and community involvement, while frequently cited in mitigation, rarely carry the day when weighed against the gravity of the offense. The blunt reality is this: the most reliable way to avoid federal prison is to avoid a federal indictment. Custodial sentences are the norm—not the exception.

In early 2025, there was considerable speculation that departures from DOJ—both prosecutors and investigators—combined with a heightened focus on violent crime and immigration enforcement, might signal a retreat from white-collar prosecutions. Eighteen months later, those concerns have not materialized. There was a temporary lull, but many offices across the country have successfully rebuilt their ranks, and prosecutors are actively pursuing cases across the full spectrum of white-collar offenses. I am currently handling several investigations that originated under the current administration, spanning a range of fraud matters. Resources that were temporarily redirected have slowly returned, and white-collar enforcement is very much alive.

Second, and perhaps more important, it remains essential to retain experienced counsel at the earliest indication that one may be connected to an investigation—even tangentially. With significant turnover in recent months, there are many newer prosecutors handling complex cases. Counsel who understands how federal investigations operate, who knows the personnel, has appeared before multiple judges, and who can navigate the current enforcement landscape can make a meaningful difference in the outcome. The right representation may well determine whether a client returns home at night or faces a very different reality.

Related TaxProf Blog coverage:

• SCOTUSblog Founder Tom Goldstein Trial: Closing Arguments (Feb. 21, 2026)
• 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)
• Did SCOTUSblog Founder Tom Goldstein Commit Tax Evasion in Hiring Four Women He Was Romantically Interested in and Who Allegedly Did Little or No Work at His Law Firm? (Nov. 16, 2025)
• SCOTUSblog Founder Tom Goldstein Rearrested on Tax Evasion Charges After Feds Say He Hid Millions in Crypto (Feb. 11, 2025)
• SCOTUSblog Founder Tom Goldstein Hit with 22-Count Federal Tax Evasion Indictment (Jan. 23, 2025)