With just over a month to go until Donald Trump’s scheduled July 11 sentencing hearing, a legal expert told Salon the former president’s lack of remorse and findings of contempt could be grounds for a jail sentence.

“When I first started thinking about this case, I thought that the judge sentencing him to incarceration was very unlikely,” said Adam Shlahet, director of the Brendan Moore Trial Advocacy Center at Fordham Law. “I'm thinking it's more likely now.”

Former Manhattan prosecutor Arthur Middlemiss said he thinks Trump will “probably” not see prison time.

“The mitigating factors in favor of a lesser sentence and probably a non-jail sentence are Trump's advanced age, the fact that he's a first time offender, and whether you like it or appreciate it or not, he's got a history of public service,” Middlemiss said.

Still, Shlahet said Trump’s put himself in an uncommonly vulnerable position ahead of sentencing because he hasn’t expressed remorse and because Judge Juan Merchan found him in contempt of court 10 times for violating a gag order.

“He can take into account all of his civil fraud, can take into account all of his contempt, and so even though this is a guy with no record and he's an older gentleman, there are a ton of factors, aggravating factors that would lead a judge to give him some jail time,” Shlahet said.

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Shlahet also pointed to Trump's conduct toward the judge.

“When the person who's going to be deciding your sentence is the judge, it's also a really good idea to not antagonize the judge at every opportunity," Shlahet said. "Every time he gets a microphone, he insults the judge and calls the judge crooked and calls the judge conflicted and shows no respect for the jury's verdict. And that is not the way a defendant who wants probation should be acting.”

Trump was found guilty of 34 counts of felony falsification of business records in a scheme that prosecutors said aimed to preserve his 2016 presidential bid through disguised hush-money payments to cover up alleged extramarital affairs.

Trump faces sentencing by Merchan – who also presided over the 2023 and 2024 sentencing of Trump’s former chief financial officer Allen Weisselberg.

In 2023, Merchan sentenced Weisselberg to five months behind bars and five years of probation after he pleaded guilty to charges that he participated in a tax fraud scheme cooked up by Trump Organization executives.........

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