Michael Cohen faces stern disciplinarian as he awaits sentencing

President Donald Trump is set to see the first sentencing in federal court of a onetime close ally for crimes that may have helped propel him to the White House.

But first, Michael Cohen may ask for leniency.

Cohen, Trump’s former personal attorney, is scheduled to be sentenced December 12 for the eight federal crimes to which he pleaded guilty in August after being charged by Manhattan federal prosecutors with tax fraud, false statements to a bank and campaign-finance violations tied to his work for Trump, including payments Cohen made or helped orchestrate that were designed to silence women who claimed affairs with the then-presidential candidate.

Trump and Cohen have been estranged since Cohen implicated Trump in court, saying he made the payments “in coordination and at the direction of a candidate for federal office.”

Cohen’s sentencing is certain to bring renewed scrutiny of his offenses — and their ties to Trump — and could provide fresh details drawn from them. And as with all sentences, his fate will hinge primarily on the perspective of the federal judge — in this case, a famously stern disciplinarian, according to attorneys who have appeared before him.

This week, Cohen’s attorney is due to submit court filings that will likely lay out why he deserves a lesser sentence.

In recent weeks, Cohen has made a public and private showing of distancing himself from his former boss, speaking multiple times with New York federal prosecutors and with special counsel Robert Mueller’s team, while also knocking the Trump administration as “craziness” in a brief interview with CNN and attempting to rebrand himself as a born-again Democrat.

The rehabilitation tour by the President’s former fixer has even included an appearance in the New York Post’s “Page Six” column earlier this month in which he was celebrated for reportedly coming to the rescue of an elderly man in an Upper East Side restaurant, where Cohen saved the man from falling, “hugged him and put him back on his feet.”

But if none of that earns Cohen a cooperation agreement with the federal government — a step that, among other consequences, would almost certainly delay his sentencing — he will be due in court.

The stipulated guideline range of Cohen’s prison term is between 46 and 63 months, according to his plea agreement, which also sets a range of fines of between $20,000 and $1 million. The judge, however, can deviate from the guidelines when he determines Cohen’s sentence, which will also take into account court filings from both sides that are due in the next two weeks. The filing from federal prosecutors is due next week.

Judge known for lengthy sentences for white-collar offenders

If Cohen is hoping for leniency, he may be out of luck with US District Judge William Pauley III, according to attorneys who have had cases before him.

“He has a very formal approach and he is not someone who takes things lightly,” Harry Sandick, a former federal prosecutor in the Manhattan US Attorney’s office who has appeared before Pauley, “and in his white-collar sentences he gives long sentences, usually consistent with the guidelines.”

Pauley declined to comment for this story. An attorney for Cohen, Guy Petrillo, didn’t respond to a request for comment.

Pauley’s strict approach to the courtroom has taken varied forms. In the case of one of the highest-profile white-collar defendants who has appeared before Pauley, Sam Waksal, the former pharmaceutical CEO who pleaded guilty in an insider trading case that also ensnared Martha Stewart, it meant the toughest-possible sentence under federal guidelines.

In 2003, Pauley sentenced Waksal to a prison term of more than seven years. In that case, Waksal’s lawyer had argued for leniency in part by noting that the defendant’s work had been in service of cancer patients. Pauley rejected it. ”The harm that you wrought is truly incalculable,” he told Waksal.

In the case of Bill Burck, the criminal-defense attorney whose clients include former White House counsel Don McGahn in the special counsel’s probe, it meant a surprising encounter with the judge when Burck was a 31-year-old federal prosecutor appearing before him in New York, according to a person familiar with the episode.

After Burck introduced himself in court using his first and last name, Pauley called him over during a sidebar conference and said to him, “government’s awfully casual.” When Burck responded with confusion, Pauley told him, “Your name is William, not Bill, and in this courtroom you’ll be known by William.”

Reached for comment, Burck confirmed the incident, adding: “Subsequent to that, I have always officially called myself William.”

Cohen could receive stiffer sentence because he’s an attorney

In Cohen’s case, one of the factors that may negatively impact the judge’s view of his crimes, said those who have appeared before Pauley, is that Cohen is himself an attorney.

“I think Judge Pauley is going to look at him as an intelligent person who had plenty of means. He wasn’t compelled into criminality by the way he was raised,” said Elie Honig, a former federal prosecutor and CNN legal analyst who had cases before Pauley, “and I think Judge Pauley is going to be particularly bothered by the fact that Michael Cohen committed these crimes … at least some of them, in his capacity as a lawyer.”

Indeed, the guideline range in Cohen’s plea agreement already contains what is known as an enhancement, or extra penalty, because he “used a special skill — to wit, his education, training and licensing as an attorney in New York State — in a manner that significantly facilitated the commission and concealment of the offense.”

Pauley can speak to that in court and take it into consideration as much as he chooses, and “in some of his sentencings he has been particularly concerned about people who are in a position to follow the law, and don’t,” Sandick said.

Another factor that is sometimes given significant weight is deterrence. Judges consider what’s known as specific deterrence — whether the sentence will cause the defendant himself to avoid the act in the future — as well as general deterrence— whether the sentence will deter others from committing similar crimes.

Pauley, according to former prosecutors, is adamant about the ability of a tough sentence to deter similar misbehavior.

“Judge Pauley is a strong deterrence judge,” said Honig. “He believes that every sentence he gives has to punish the person in front of him, but also send a message to others.”

In Cohen’s case, the judge must consider what sentence will serve to dissuade not only potential offenders of campaign-finance laws, but also those tempted to commit tax fraud or lie to a bank.

And finally, a judge will often weigh whether a defendant has demonstrated an appropriate level of remorse for their behavior. Pauley isn’t known to give heavy consideration to that element, according to people who have appeared before him, but it will likely arise in the court filings that are due from both prosecutors and Cohen’s defense counsel, particularly since Cohen’s plea agreement contains a provision that he will receive a reduction in his sentence “assuming the defendant clearly demonstrates acceptance of responsibility, to the satisfaction of the Government.”