His high-flying legal practice couldn’t save him from the even higher-flying lifestyle he was pursuing away from the bar.

You might think that Tom Goldstein would be enjoying the pinnacle of respectability in the legal profession right now. As a young lawyer, he was at the side of David Boies and Laurence Tribe for the Democratic team arguing Bush v. Gore. Now at the peak of professional life in his mid-50s, Goldstein has argued 44 cases before the U.S. Supreme Court. His bio recites that “Only 3 lawyers in the court’s modern history have argued more cases in private practice. He has been counsel on more successful petitions for certiorari over the past decade than any other lawyer in private practice. Over the past 15 years, the firm’s petitions for certiorari have been granted at a higher rate than any private law firm or legal clinic.” He has taught Supreme Court Litigation at Harvard Law School since 2004, after teaching the same topic at Stanford. He is one of the co-founders and publisher of SCOTUSblog, the must-read site covering the Court. He holds a number of positions of distinction in the bar.

It might seem puzzling that a man in this position would retire from appellate practice in 2023. It might seem even odder when juxtaposed against Goldstein’s reputation. Noam Scheiber profiled him in 2006 for the New Republic as “The Hustler,” for his aggressive pursuit of clients with cases that were headed to the Court or suitable for its docket (Scheiber contrasted his methods to the more genteel approach of Carter Phillips, my law firm’s top Supreme Court advocate and one of the deans of the Supreme Court bar). SCOTUSBlog grew out of that same entrepreneurial, risk-taking, pushing-the-envelope spirit. So did his boutique law firm, Goldstein & Russell, which often took cases aligned with the anything-goes plaintiffs’ bar. If I were writing a novel about a seemingly respectable lawyer who couldn’t outrun his fundamental character flaws, I could not ask for a better detail than the fact that his middle name is Che.

If even half of today’s 22-count federal indictment of Goldstein is to be believed, there was a lot to outrun, and it caught up with Goldstein. His alleged dark side: He “was also an ultrahigh-stakes poker player, frequently playing . . . in the United States and abroad involving stakes totaling millions, and even tens of millions, of dollars.” He financed that by “borrowing millions of dollars” or getting people to stake him in exchange for a share of his winnings — if he won. At times, he won big: The indictment recites a $13.8 million win in Hong Kong in 2016 and taking a California businessman for $26 million in Beverly Hills that same year. But he also frequently held gambling debts approaching $10 million.

Then there’s women: He “was involved, or pursued, intimate personal relationships with at least a dozen women, transferring hundreds of thousands of dollars to them” in addition to the other costs of their travel and expenses. He allegedly “hired” four of them as sham employees of his firm to get them health insurance. He was otherwise allegedly using the firm as a personal piggy bank to cover his lifestyle.

He was able to get away with this within the firm because he owned it, and because “G&R did not employ an in-house accountant or bookkeeper. Rather, limited record-keeping functions were carried out by G&R’s ‘firm manager,’ who was typically a recent college graduate with no formal accounting or bookkeeping experience” and was also kept busy as a go-fer doing things like picking up Goldstein’s dry cleaning.

Where the law gets involved is mostly tax evasion — 19 counts of unpaid taxes, willful failure to pay taxes, and false and fraudulent tax returns. There are also three counts of false statements on mortgage loan applications he took out to cover his debts.

Goldstein’s a smart lawyer, and even aside from his impact on the Supreme Court bar, his blog alone has had a major impact on how lawyers keep up with the Court. But if the story told in his indictment is true, even his high-flying legal practice couldn’t save him from the even higher-flying lifestyle he was pursuing away from the bar.