As a young lawyer, Nicholas Gravante made an unusual choice: he left Cravath, Swaine & Moore, one of America’s oldest and most prestigious law firms, to go and work for Gerald Shargel, a criminal lawyer. from New York whose clients included Mafia bosses. and drug dealers.
Working for Shargel has helped make Gravante one of the best litigators and white collar lawyers in town. In a roundabout way, it also got him in the midst of one of the biggest cases of the time: Manhattan District Attorney Cyrus Vance’s investigation into former President Donald Trump and Trump. Organization.
This investigation intensified this month with the grand jury charge Allen Weisselberg, longtime chief financial officer of the Trump Organization, for alleged tax evasion.
Weisselberg, who once described himself as Trump’s “eyes and ears”, is accused of accepting free rent, cars and tuition for his company grandchildren without paying taxes on these advantages. He has pleaded not guilty, although prosecutors hope he may be made to turn against Trump and strike a deal to facilitate their investigation.
In the meantime, according to people with knowledge of the investigation, they are now examining another member of the Trump organization’s leadership for similar violations: Matthew Calamari, the chief operating officer.
Calamari retained Gravante to represent him. He did so on the recommendation of Alan Futerfas, a lawyer for the Trump Organization, who was one of the young partners of “Jerry” Shargel when Gravante joined the law firm in 1990.
“The circle has come full circle and now we’re sort of in the spotlight on a high-profile case where it used to be our boss, Jerry, who was in the spotlight every day,” said Gravante, 60. “I really appreciate him, I have to say.”
Vance’s office gives Gravante the opportunity to explain why his client shouldn’t be charged, as they did for Weisselberg. Gravante was reluctant to preview his defense arguments, but made it clear that he intended to argue that there were clear distinctions between Trump’s two lieutenants.
While Weisselberg was a trained accountant and CFO, the beefy Calamari is a former American football player who caught Trump’s attention after facing a rowdy at the 1981 US Open tennis tournament while he was working as a security guard during the event. He joined Trump as a bodyguard and while accompanying the boss to construction sites over the years, he learned the ins and outs of project management before eventually getting into the organization.
“He’s not even a college graduate – he’s a security guy,” Gravante said. “He has no financial sophistication!
Calamari had a Trump apartment in Manhattan and a company car, but they were essential to his job to keep the family and their property safe, Gravante argued, and the cost was deducted from his salary.
He will be arguing his case with Mark Pomerantz, another veteran New York defense attorney, who left private practice earlier this year to help Vance’s investigation. Pomerantz taught contract law and criminal defense at Gravante at Columbia Law School. “It’s a small world,” Gravante said.
Besides media attention – and reuniting with old friends – Gravante sees the case as a vital precedent for the possible prosecution of a former president by political opponents.
“When you go down this path, it’s a really dangerous path for the country,” said Gravante, who has also represented Hunter Biden and is close to several New York Democrats, including Senator Kirsten Gillibrand.
He added: “That’s why it’s a really interesting case – not just because of the players, not just because of the press attention, but because I don’t think we’ve ever been in a situation. like this before, and it’s going to be interesting to see how that plays out.
Vance and Letitia James, the New York attorney general, both Democrats who have been elected to their posts, argue that the investigation aims to confirm a different precedent: that no one – even a former president – is au- above the laws.
Gravante grew up in Bay Ridge, Brooklyn, the son of a local real estate attorney who prepared taxes for, among others, mafia hitman Salvatore “Sammy the Bull” Gravano.
Prior to the Trump case, Gravante made headlines for his role at Boies Schiller Flexner, the litigation firm founded by a great lawyer David Boies. Gravante, a protégé of Boies, was elected co-manager at the end of 2019 in an attempt to stabilize a company that was bleeding talent after a series of missteps, including Boies’ portrayal of Harvey Weinstein, and his involvement with Theranos, the allegedly fraudulent start-up of blood tests.
Gravante pushed for a merger with Cadwalader, Wickersham & Taft, and then decamped himself when that effort failed. “I thought Boies Schiller should have merged with Cadwalader. I fought to make this happen. That didn’t happen, ”he said, calling his new job an opportunity to work with a team of“ stars ”that has an impressive list of financial services clients.
While he praises Boies as “the greatest litigator of our generation,” Gravante may end up relying more on his Shargel experience if prosecutors indict Calamari. “Jerry taught me everything about being a litigator,” said Gravante, recalling how difficult it was to gain courtroom experience in a large firm. “During the two years that I worked for him, I lived in court.
Shargel’s office was a far cry from Cravath, where Gravante had struggled over sprawling cases like the 1980s Texaco-Pennzoil litigation. “We had organized crime cases, there were drug cases. The clients who came to the office were people accused of crimes. Many of them have been convicted. It was a very, very different atmosphere. It was like night and day.
Among the lessons Shargel gave Gravante: read everything. While other criminal lawyers asked assistants to prepare summaries of depositions and other trial documents, Shargel himself overturned the underlying documents. It was the only way to prepare in case a witness might say something unexpected during cross-examination.
Shargel, who won the acquittal of New York Mafia boss John Gotti in 1990 (he was later convicted on separate charges), also stressed the importance of credibility.
“You can state 20 points in an opening statement, you get one that ends up being wrong, you’re going to get your head hammered with that all through the trial,” Gravante said. “So you know what?” You stick to the 19 sure things. You are not exaggerating anything. Because once your credibility is down, it’s a disaster.
Other lessons were more subtle – like how to grab the podium, how to respond to a judge, and the need to kiss a client at all times, even one you don’t particularly like.
“Everyone watches and always makes impressions,” observed Gravante. “If you come back with your client after lunch – if you seem like you don’t really like your client and there is this perception that you don’t get along, why should someone else on the jury love them? ”
If you see Gravante smiling alongside Calamari in the days to come, it can be a real affection. Or, it can be the wisdom of Jerry Shargel.