“A ton of aggravating factors”: Experts say Trump not helping himself ahead of sentencing hearing

Jail previously seemed "very unlikely," says law prof. Adam Shlahet. “I'm thinking it's more likely now”

By Marina Villeneuve

Staff Reporter

Published June 8, 2024 6:00AM (EDT)

Former US President Donald Trump attends the second day of his trial for allegedly covering up hush money payments linked to extramarital affairs, at Manhattan Criminal Court in New York City on April 16, 2024. (MARK PETERSON/POOL/AFP via Getty Images)
Former US President Donald Trump attends the second day of his trial for allegedly covering up hush money payments linked to extramarital affairs, at Manhattan Criminal Court in New York City on April 16, 2024. (MARK PETERSON/POOL/AFP via Getty Images)

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.

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. Weisselberg ended up serving 100 days at Rikers Island last year.

And in April, Merchan sentenced Weisselberg to five months behind bars after he was convicted of two counts of perjury in the first degree.

Bennett Gershman, law professor at Pace University, pointed out that Weisselberg got sentenced to jail time despite his own mitigating factors.

Weisselberg, 76, had no criminal record, like his former boss. 

Trump, Gershman said, has “probably more aggravating circumstances than any white collar criminal in history.”

But Trump’s case does differ from Weisselberg’s in several key ways, said Middlemiss.

“Probably the most important mitigating factor is that the crimes that he was convicted of were the lowest level felonies in New York,” Middlemiss said. “Unlike a violent crime or a crime where you steal money from an individual, there's no real identifiable victim.”

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Felony falsification of business records is a Class E felony – the lowest level of felony – in New York state.

Meanwhile, Weisselberg was charged and convicted of falsifying business records along with “more serious felonies,” Middlemiss said. 

Weisselberg pleaded guilty to 15 felonies in all, including grand larceny in the second degree – a Class C felony. 

Weisselberg agreed to pay $1.9 million in back taxes and penalties and to testify at the Trump Organization’s trial.

“Which makes it a big tax case,” Middlemiss said. “You would consider that to be a definable victim in that the city and the state didn't get the taxes that it was owed because he didn't pay them, which is a more easily definable victim than the entire electorate writ large.”

Prosecutors had said Trump’s scheme defrauded the voting public.

This spring, Weisselberg pleaded guilty to two counts of perjury in the first degree concerning his 2020 deposition to the attorney general’s office. 

Felony perjury in the first degree is a class D felony and has a maximum sentence of seven years in prison in New York. The Associated Press reported that prosecutors “cited Weisselberg’s age and willingness to admit wrongdoing” in agreeing to the five month sentence.

Middlemiss said Trump does face factors that “would weigh in favor of a more serious sentence.”

“Trump, on the other hand, was completely unrepentant, didn't admit guilt, never acknowledged that he was sorry, that he did these things, and was completely contentious of the court and the process by which he was convicted,” Middlemiss said.

Trump could face a fine of up to $170,000 – if the judge fines him a maximum of $5,000 per offense for each of the 34 counts. 

He could also receive probation, community service, or what’s known as a conditional discharge.

Any sentence for Trump would pose logistical complications: community service would be tricky for a high-profile presidential candidate, probation raises questions about how Trump could campaign across the country, while the Secret Service would join him at jail. 

The judge could impose a sentence of conditional discharge if he decides “neither the public interest nor the ends of justice would be served by a prison of imprisonment and that probation supervision is not appropriate.”

Conditional discharge would mean that instead of a jail sentence, the judge could impose restrictions on Trump – including barring him from breaking the law for a period of time.

The period of conditional discharge “shall be” three years for felonies, according to state law. 

Each of the 34 counts has a maximum four-year prison sentence, and he’s expected to serve any sentence concurrently. 

Trump would serve time at a jail such as Rikers Island if he gets a sentence of less than a year – while he could serve in a state prison if he gets more than a year behind bars.

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In a Fox News interview Wednesday, Trump called the legal system corrupt and said: “I did nothing wrong in any of these things. I did nothing wrong. We did nothing wrong at all.”

Trump also said: “They are doing it for the purposes of hurting a political opponent of Biden and trying to get him to win. Everybody said this is such a minor thing, you don’t go to jail for this.”

Once Trump gets sentenced, an appeal would put any jail, probation, fine or community service sentence on hold for a potentially years-long appeals battle.

Middlemiss said he’d likely successfully request bail pending appeal if he is sentenced to jail time.

“He’ll probably get it, and he probably should get it because he has no criminal history,” Middlemiss said. “It’s not like he’s going anywhere. It’s not like he’s going to flee the United States to avoid incarceration… The risk of flight would be minimal for anyone in these particular circumstances based on the severity of the crime and the likelihood of incarceration, but it's particularly low when you got a guy who's running for president of the United States, we know where he's going to be every day.”

Ahead of the July 11 sentencing, Trump is expected to meet with the probation office, according to Shlahet.

“Either a probation officer or a social worker, someone who works for probation, and they're going to interview him and then make a sentencing recommendation,” he said. “Normally, this is to get kind of some vital information about the defendant: what their history is, what their criminal history is, what their community ties are, are they working, all that kind of stuff.”

Shlahet said he’s interested in one question Trump will face: about his case, and whether he accepts responsibility. 

“That's a really big thing that the judge looks at,” he said.

Shlahet said that “a lot of the restrictions that are placed on people with a felony conviction are just not going to apply to him.”

“He’s going to get waivers to any country he wants to visit if he’s the president of the United States,” he said. “If he loses the election, then I think these collateral consequences may become inconvenient.”

Over the past week, Trump has complained that the July 11 sentencing data is unfair because it’s just days before he is expected to be named the GOP presidential nominee at the Republican National Convention in Milwaukee, which begins July 15.

Trump said on his social media platform that the July 11 date was set “conveniently for the fascists."

On May 30, Trump sat in the courtroom as his defense attorney asked for a date in mid-to-late July. 

“The reason for that is, as the Court is aware, President Trump faces other charges in other jurisdictions,” defense lawyer Todd Blanche said. “In the case in Florida, there is a three-day hearing scheduled for late July.”

Blanche did not object when Merchan set sentencing for July 11.

“That is definitely a date that his attorneys agreed to in front of him,” Shlahet said. “Donald Trump didn’t voice any protest at that time, but now he is.”

Shlahet said the quicker the sentence – the sooner Trump can begin the appeals process. 

By Marina Villeneuve

Marina Villeneuve is a staff reporter for Salon covering Trump's legal battles and other national news focusing on major legal and political narratives.

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