As a young lawyer, Nicholas Gravante made an unusual choice: he left Cravath, Swaine & Moore, one of the oldest and most prestigious law firms in the US, to work for Gerald Shargel, a New York City criminal defense attorney who, among others, deals with mob bosses. to his clients. and drug dealers.
Working for Shargel, Gravante became one of the city’s top trial attorneys and white-collar attorneys. In a roundabout way, it has also put him right in the middle of one of the greatest cases of the era: Manhattan district attorney Cyrus Vance’s investigation into former President Donald Trump and the Trump Organization.
That investigation escalated this month with the grand jury charge van Allen Weisselberg, the longtime chief financial officer of the Trump Organization, for alleged tax fraud.
Weisselberg, who once described himself as Trump’s “eyes and ears,” is accused of accepting free rent, cars and school fees for his grandchildren from the company without paying taxes on those benefits. He pleaded innocent, although prosecutors hope he could be led to turn on Trump and strike a deal to facilitate their investigation.
In the meantime, according to people briefed on the investigation, they are now investigating another member of the Trump Organization’s executive suite for similar violations: Matthew Calamari, its chief operating officer.
Calamari has retained Gravante to represent him. He did this on the recommendation of Alan Futerfas, a lawyer for the Trump Organization, who happened to be one of “Jerry” Shargel’s young associates when Gravante joined the law firm in 1990.
“It’s come full circle and now we’re kind of in the spotlight in a very high-profile business, where it used to be our boss, Jerry, who was in the spotlight every day,” said 60-year-old Gravante. “I really enjoy it, I must say.”
Vance’s office gives Gravante a chance to argue why his client shouldn’t be charged—just like they did for Weisselberg. Gravante was reluctant to preview his defense arguments, but made it clear that he intends to argue there is a clear distinction between the two Trump lieutenants.
While Weisselberg was an accountant by training and CFO, the burly Calamari is a former American football player who came to Trump’s attention after tackling a heckler at the US Open tennis tournament in 1981 while working as a security guard at the event. He joined Trump as a bodyguard and as he mentored the boss on construction sites over the years, he learned the ins and outs of project management before eventually growing in the organization.
“He’s not even a graduate, he’s a security guy,” Gravante said. “He has no financial sophistication!”
Calamari did own a Trump apartment in Manhattan and a company car, but those were essential to his job as security for the family and their property, Gravante argued, and the expenses were deducted from his salary.
He will take his case to Mark Pomerantz, another veteran New York attorney who left private practice earlier this year to aid Vance’s investigation. Pomerantz taught Gravante contract law and criminal defense at Columbia Law School. “It’s a small world,” Gravante said.
Aside from the media attention – and the reunion with old friends – Gravante considers the case a crucial precedent for the possible prosecution of a former president by political opponents.
“If you go down this road, it’s a very dangerous road for the country,” said Gravante, who has also represented Hunter Biden, and who is close to several New York Democrats, including Senator Kirsten Gillibrand.
He added: “That’s why it’s a really interesting thing – not just because of the players, not just because of the press attention, but because I don’t think we’ve ever experienced a situation like this, and it will be. interesting to see how it unfolds.”
New York Attorney General Vance and Letitia James, both Democrats elected to their posts, claim the investigation is about establishing another precedent: that no one — even a former president — is above the law.
Gravante grew up in Bay Ridge, Brooklyn, the son of a local real estate attorney who prepared taxes for convicted mob hitman Salvatore “Sammy the Bull” Gravano, among others.
Before the Trump case, Gravante made headlines for his role at Boies Schiller Flexner, the trial agency founded by superlawyer David Boies. Gravante, a Boies protégé, was elected co-managing partner in late 2019 to try to stabilize a company that was bleeding talent after a series of missteps, including Boies’ representation of Harvey Weinstein, and his involvement with Theranos, the allegedly fraudulent start blood tests.
Gravante pushed for a merger with Cadwalader, Wickersham & Taft, then left when that attempt failed. “I did believe that Boies Schiller should have merged with Cadwalader. I fought to make that happen. It didn’t happen,” he said, calling his new job an opportunity to work with an all-star team with an impressive number of financial services clients.
While touting Boies as “the greatest trial attorney of our generation,” Gravante can ultimately draw on more of his Shargel experience as prosecutors indict Calamari. “Jerry taught me all about being a trial attorney,” said Gravante, who recalled how hard it was to get to a large firm of courtroom experience. “The two years I worked for him, I lived in court.”
Shargel’s company was a far cry from Cravath, where Gravante had toiled on sprawling corporate cases, such as the Texaco-Pennzoil lawsuits in the 1980s. “We had organized crime cases, there were drug cases. The clients who entered the office were people accused of crimes. Many of them were convicted. It was a very, very different atmosphere. It was like day and night.”
Among the lessons Shargel gave Gravante: read everything. While other criminal defense attorneys had assistants to prepare affidavits and other trial documents, Shargel himself poured over the underlying materials. It was the only way to be prepared in the event that a witness said something unexpected during cross-examination.
Shargel, who famously won the 1990 acquittal of New York mob boss John Gotti (he was later convicted on separate charges), also stressed the importance of credibility.
“You can mention 20 points in an opening statement. If you end up with one that’s wrong, you’re going to be hammered through the entire trial with it,” Gravante said. “So you know what? You stick with the 19 certain things. You don’t exaggerate anything. Because once your credibility is down, it’s a disaster.”
Other lessons were more subtle — like how to take the stage, how to respond to a judge, and the need to always embrace a client, even one you don’t like very much.
‘Everyone is always looking and forming an impression,’ Gravante remarked. “If you’re walking back from lunch with your client — if you look like you really don’t like your client, and there’s this perception that you don’t get along with, why would anyone else on the jury like him?”
Seeing Gravante smiling next to Calamari for the next few days could be genuine affection. Or maybe it’s Jerry Shargel’s wisdom.