The Trump investigation lawyer who served a valuable apprenticeship

As a young lawyer, Nicholas Gravante made an unusual choice: he left Cravath, Swaine & Moore, one of the oldest and most prestigious US law firms, to go to work for Gerald Shargel, a New York City criminal lawyer whose clients included mob bosses and drug dealers.

Working for Shargel helped make Gravante one of the city’s top litigators and white collar lawyers. In a roundabout way, it has also landed him in the middle of one of the era’s biggest cases: Manhattan district attorney Cyrus Vance’s investigation of former president Donald Trump and the Trump Organization.

That investigation escalated this month with the grand jury indictment of Allen Weisselberg, the Trump Organization’s longtime chief financial officer, for alleged tax fraud.

Weisselberg, who once described himself as Trump’s “eyes and ears”, is accused of accepting free rent, cars and school tuition for his grandchildren from the company without paying taxes on those benefits. He has pleaded not guilty, although prosecutors are hoping he might be induced to turn against Trump and strike a deal to aid their investigation.

In the meantime, according to people briefed on the probe, they are now scrutinising another member of the Trump Organization’s executive suite for similar violations: Matthew Calamari, the chief operating officer.

Calamari has retained Gravante to represent him. He did so based 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 are sort of in the limelight in a very high-profile case whereas in the old days it was our boss, Jerry, who was in the limelight every day,” Gravante, 60, said. “I’m really enjoying it, I have to say.”

Vance’s office is giving Gravante an opportunity to argue why his client should not be charged — just as they did for Weisselberg. Gravante was reluctant to preview his defence arguments, but made it clear he intends to argue there are clear distinctions between the two Trump lieutenants.

While Weisselberg was an accountant by training, and the CFO, the beefy 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 while accompanying the boss around constructions sites over the years he learned the ins and outs of project management before eventually rising in the organisation.

“He’s not even a college graduate — he is a security guy,” Gravante said. “He has no financial sophistication whatsoever!”

Calamari did have a Trump apartment in Manhattan and a company car, but they were essential to his job providing security for the family and their properties, Gravante argued, and the cost was deducted from his salary.

He will be making his case to Mark Pomerantz, another veteran New York defence lawyer, who left private practice earlier this year to help Vance’s investigation. Pomerantz taught Gravante contract law and criminal defence at Columbia Law School. “It’s a small world,” Gravante said.

Apart from the media attention — and the reunion with old friends — Gravante views the case as a vital precedent for the possible prosecution of a former president by political adversaries. 

“When you go down this road, 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 only because of the players, not only because of the press attention, but because I don’t think we’ve ever experienced a situation like this before, and it’s going to be interesting to see how it unfolds.”

Vance and Letitia James, the New York attorney-general, both Democrats who were elected to their posts, argue the investigation is about confirming a different precedent: that nobody — even a former president — is above the law.

Gravante grew up in Bay Ridge, Brooklyn, the son of a local real estate lawyer who prepared taxes for, among others, convicted mafia hitman Salvatore “Sammy the Bull” Gravano.

Before the Trump case, Gravante made headlines for his role at Boies Schiller Flexner, the litigation firm founded by super lawyer David Boies. Gravante, a Boies protégé, was elected co-managing partner in late 2019 to try to stabilise a firm that was haemorrhaging talent after a series of missteps, including Boies’ representation of Harvey Weinstein, and his involvement with Theranos, the allegedly fraudulent blood-testing start-up. 

Gravante pushed for a merger with Cadwalader, Wickersham & Taft, and then decamped there himself when that effort failed. “I did believe that Boies Schiller should have merged with Cadwalader. I fought for that to happen. It did not happen,” he said, calling his new job an opportunity to work with a team of “all-stars” that has an impressive roster of financial services clients.

While he praises Boies as “the greatest litigator of our generation”, Gravante may end up drawing more on his Shargel experience if prosecutors charge Calamari. “Jerry taught me everything about being a trial lawyer,” Gravante said, recalling how difficult it was to come by courtroom experience at a big firm. “For the two years I worked for him, I lived in court.”

Shargel’s firm was a far cry from Cravath, where Gravante had toiled on sprawling corporate cases like the 1980s Texaco-Pennzoil litigation. “We had organised crime cases, there were drug cases. The clients who came into the office were people who were charged with crimes. Many of them were convicted. It was a very, very different atmosphere. It was like night-and-day.”

Among the lessons Shargel imparted to Gravante: read everything. While other criminal lawyers had assistants prepare summaries of depositions and other trial documents, Shargel poured over the underlying materials himself. It was the only way to be prepared in the event that a witness might say something unexpected during a cross-examination.

Shargel, who famously won the acquittal of New York mob boss John Gotti in 1990 (he was later convicted on separate charges), also emphasised the importance of credibility.

“You can state 20 points in an opening statement, you get one of them that ends up being wrong you’re going to get hammered over the head with that throughout the trial,” Gravante said. “So you know what? You stick with the 19 sure things. You don’t overstate anything. Because once your credibility is shot, it’s a disaster.”

Other lessons were more subtle — like how to seize the podium, how to respond to a judge, and the need to embrace a client at all times, even one you do not particularly like.

“Everyone’s always watching and forming impressions,” Gravante observed. “If you’re walking back with your client from lunch — if you look like you really don’t like your client, and there’s this perception you don’t get along, why should anyone else in the jury like them?” 

If you see Gravante smiling alongside Calamari in the days ahead, it may be genuine affection. Or, it may be the wisdom of Jerry Shargel.

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