What a tax evader sentenced by Judge Chutkan means for Donald Trump

If Donald Trump ever faces sentencing in the courtroom of U.S. District Judge Tanya Chutkan for his bid to subvert the 2020 election, he may want to study the case of Stephen Schechter.

Schechter, an investment banker, appeared before Chutkan on Friday to be sentenced after pleading guilty to concealing $5.1 million from the IRS that he had stashed overseas.

On paper, the cases have little in common. Trump, a former president, is charged with conspiring to disenfranchise millions of voters and coerce government officials to throw out the lawful results of the election he lost. Schechter, a relatively anonymous businessman, hid the proceeds of an overseas real estate transaction from the IRS.

But Schechter, like Trump, is in his late 70s. And Chutkan dwelled extensively Friday on his advanced age when determining his sentence. She described an extreme reluctance to sending the 79-year-old to prison — particularly one she said was in “frail health” — even as she wrestled with the need to punish a white collar criminal and show that there are “rules that apply to everyone.”

“I don’t view this as a victimless crime,” Chutkan said.

Every time Chutkan sentences a defendant, she offers a glimpse of her judicial philosophy in ways that may come to bear in Trump’s case, which is on hold while the Supreme Court weighs his bid for immunity from the charges.

Some legal observers have noted that Chutkan, a former public defender, has often handed down tough sentences for rioters convicted in Jan. 6 cases, inferring that she would apply a similarly tough approach to Trump. But those cases are not monolithic, and Chutkan has at times drawn stark distinctions among them.

For example, she recently scolded the Justice Department for seeking a maximal sentence for Michael Foy, a Jan. 6 defendant who assaulted police with a hockey stick but has also suffered from mental health challenges and spent two years trying to turn his life around. Chutkan also recently made accommodations for a Jan. 6 defendant who is a nursing mother, delaying her sentence for months.

At other times, Chutkan has decried advantages given to Jan. 6 defendants — who often appear at their hearings remotely and have, in her view, been offered generous plea deals — and recoiled at what she sees as disparate treatment for privileged offenders.

On Friday, Chutkan sentenced Schechter to seven days in jail, sharply below the two years requested by prosecutors. Chutkan said she believed that a sentence without jail would have have sent the wrong message “in a country that believes in the rule of law.”

“There have to be consequences,” she said.

But Chutkan repeatedly tempered her comments by citing Schechter’s age. She said she was “worried” about what even a weeklong sentence would mean for Schechter in Washington, D.C.’s jail.

“I don’t have a lot of confidence in the D.C. jail,” Chutkan said. “It is not a good place.”

As a result, she said, she called up the general counsel of the facility to strongly encourage that Schechter be housed in the jail’s “Central Detention Facility,” a separate cell block with medical services on hand. Coincidentally, that is where many Jan. 6 defendants have been held, both while awaiting their trials and after conviction.

Federal judges are required to consider, and publicly describe, several factors when they impose a sentence. Among them: the seriousness of the crime, the life circumstances and criminal history of the defendant and the need to deter others from committing similar crimes. Judges often receive recommendations from prosecutors, defense attorneys and probation officers, which tend to guide the final sentence, but they often have discretion to deviate from those recommendations.

In light of the delays caused by the Supreme Court’s review of the immunity issue, Trump is unlikely to stand trial in the federal election case until late summer or this fall, at the earliest. By that point, he will be 78 years old, and if convicted would be approaching his 79th birthday at the time of sentencing.

To be sure, Chutkan’s relatively light touch with Schechter was not limited to his age. She noted that aside from the crime he confessed to, he had lived “an exemplary life.” He expressed remorse for his actions, immediately “fessed up” when confronted by the IRS and took steps to right the wrong he committed. She also cited the care he provides for his 79-year-old wife, his history of military service and the impending birth of his fourth grandchild.

His grandchildren, she said, “are going to be looking to see how you live your life after this.”