For Weisselberg’s lawyer, a case like no other

(Reuters) – Allen Weisselberg, the former chief financial officer of the Trump Organization, left a Lower Manhattan courtroom on Tuesday to begin his five-month sentence at Rikers Island, and as his lawyer Nicholas Gravante told me, the 75-year-old client “just wants to get it over with.”

“He’ll be out in April,” assuming credit for good behavior, Gravante said. Weisselberg pleaded guilty in August to conspiring with former president Donald Trump’s real estate company in a 15-year tax fraud.

For Gravante, who co-heads the 90-lawyer litigation department at Cadwalader, Wickersham & Taft and whose previous clients include Hunter Biden and the musician formerly known as Kanye West, the Weisselberg representation has been “unlike any other case I’ve ever handled .”

It struck me as requiring a precarious balancing act. On one hand, the lawyer had to effect Weisselberg’s cooperation with prosecutors. On the other hand, his client still holds longstanding loyalty to the Trump family. Weisselberg, who has worked for the Trumps for half a century, said at the Trump Organization’s criminal trial in November that he acted for his own benefit, blaming “my own personal greed.”

Gravante noted that his client offered no testimony implicating “anyone with the last name Trump.” (The former president and his children were not personally charged, and the organization has vowed to appeal its conviction.)

At the same time, Weisselberg’s testimony was key for the Manhattan DA’s office in winning a conviction against the Trump Organization.

In December, New York state court jurors found two Trump companies guilty of paying personal expenses for executives including Weisselberg without reporting the income, as well as giving them bonuses as non-employee compensation to save on taxes.

“In Manhattan, you have to play by the rules no matter who you are or who you work for,” District Attorney Alvin Bragg Jr. said in a statement on Tuesday.

Gravante said he advised his elderly client to make a deal with prosecutors rather than roll the dice at trial, where he would have faced a five-to-15-year prison sentence if he lost.

It was “highly unlikely he was going to get a fair trial in New York County because of the jury pool,” Gravante said. If the proceedings were in a more politically conservative area, he added — for example, Naples, Florida, where Gravante was staying when we spoke by phone on Sunday afternoon — “my advice might have been different.”

In a statement delivered outside the courthouse on Tuesday, Gravante said his client “regrets the harm his actions have caused to the Trump Organization and members of the Trump family.”

A registered Democrat with “middle of the road” political views, Gravante said his Trump-world entrée came via Alan Futerfas, a longtime lawyer for the Trump Organization. The two worked together more than 30 years ago as associates for the late criminal defense lawyer Gerald Shargel, whose prominent clients included alleged mob bosses.

Futerfas called Gravante “one of the outstanding lawyers in the United States, which is why I recommended him to the Trump Organization.”

Gravante, who earned his law degree from Columbia Law School in 1985, started his career at Wall Street law firm Cravath, Swaine & Moore but left after five years to work for Shargel.

It was “one of the most unorthodox career decisions ever, as many people pointed out to me, but also one of the best,” Gravante said.

The draw? Courtroom experience.

“I really learned how to try cases from Jerry,” Gravante said, absorbing lessons such as the importance of appearing to genuinely like your client when, for example, walking out of court together for lunch. “It can have an influence on how the jurors assess the defendant,” he said.

Gravante reunited with Cravath colleague David Boies in 2000, spending the next two decades at Boies Schiller Flexner, where he rose to become co-managing partner before moving to Cadwalader in 2021.

While at Boies Schiller, Gravante represented then-Senator Joe Biden’s son Hunter and brother James in an investor dispute stemming from their purchase of a hedge fund in 2006. One case was dismissed and the other settled.

Perhaps less political but more controversial has been Gravante’s work at Cadwalader on behalf of Ye.

Gravante represented the rapper last fall in terminating his partnership with The Gap when Ye tweeted stunning antisemitic statements.

“When our firm took on Ye as a client, we competed against many top law firms for the work,” he said. “Circumstances change.”

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