The Making of a White-Collar Legend: Nicholas Gravante

He's represented the likes of Hunter Biden, Senior Trump Officials and Kanye West in his winding career

It’s what trial lawyers live for.

Early this year, Nicholas Gravante Jr. was everywhere, all at once. As lawyer to Trump CFO Allen Weisselberg, Gravante appeared in news accounts worldwide accompanying his client, who was being fed into a wood chipper in pursuit of The Don. As in, former President Donald Trump.

A true loyalist, Weisselberg would not flinch. He either would not or could not truthfully testify against the former President. We may never know which. But he did testify against his former employer, The Trump Organization, in the New York criminal trial against two Trump companies accused of paying personal expenses for Weisselberg and others without reporting the income. Pursuant to a deal Gravante negotiated, Weisselberg pled guilty and, at the age of 75, served 100 days in Rikers Island. He received the benefit of that universally-acclaimed sweetheart deal after being found by the court to have testified truthfully at trial. Weisselberg’s testimony did not implicate any individual whose last name began with a capital T. The Trump companies on trial were found guilty and are appealing the convictions.

Gravante says the Weisselberg representation was the second-trickiest of his career. The first? It involved a day in court in Brooklyn, his mother and dead horses. And that day was 9/11.

Any trial lawyer who wants to dance in the spotlight of the American justice system these days could take notes from Gravante, whose prodigious career in recent years has also involved Hunter Biden and Kanye West. Now there’s a Bingo card you probably didn’t have.

But Gravante did, thanks to years in the trenches alongside legends from Cravath to the late Jerry Shargel and, for much of his career, David Boies. He’s often quoted as saying he was lucky to have the best criminal lawyer (Shargel) and best civil litigator (Boies) of our generation as mentors. Now the Co-head of Litigation at Cadwalader, Lawdragon named Gravante a Legend in 2018. In addition to high-profile engagements, he’s also shuttling among numerous business disputes while helping build out Cadwalader as a destination litigation firm.

Lawdragon: Nick, what are you working on these days? You’ve had such a busy last few years with high-profile matters.

Nicholas Gravante: Several matters right now – all busy at once it seems, but thankfully I’ve got a great support team.

In the civil area, I’m defending a major New York-based real estate firm in an antitrust, class action case recently filed against most of the industry in Tennessee Federal Court. I’m involved in two antitrust actions pending against Google in the Central District of California. My work with Phil Iovieno, one of the best antitrust lawyers in the business, also continues in price-fixing actions pending throughout the country on behalf of, among others, clients, B.J.’s, McDonalds, Costco, Wendy’s, Target, Kraft-Heinz, Panda Express, Darden Restaurants (which recently acquired another of our clients, Ruth’s Chris) and Winn-Dixie.

In the white-collar area, I can only describe matters of public record. My defense of Susan Gore, heiress to the GORE-TEX empire, in connection with a D.C.-based federal grand jury investigation is taking up a fair bit of my time. So is my defense of a New York-based construction company against a bid-rigging indictment in New York Supreme Court.

Typical of my white-collar practice, I’m also representing clients in pending investigations whose identities I can’t disclose. Hopefully no one will ever learn of those matters because I will put them to bed. That’s an unusual, yet typical, feature in the life of a white-collar criminal defense lawyer. Often you can’t talk about – and no one ever learns about – many of your most successful matters.

LD: Anything else you can tell us about the alleged Wyoming spy ring that Susan Gore is being investigated in connection with?

NG: Unfortunately, there is little more I can discuss about Susan Gore aside from what has already been reported in the press. My partner, Phara Guberman, and I are representing her in connection with an ongoing federal grand jury investigation. Project Veritas, political espionage, former MI6 operatives, and spying on political opponents all make for interesting reading, but Susan is a lovely woman who has not broken any law. Like many of my clients, she was referred to me by a satisfied, former client.

That’s a typical feature in the life of a white-collar criminal defense lawyer. Often you can’t talk about – and no one ever learns about – many of your most successful matters.

LD: You were in the headlines frequently in the past year for your universally-acclaimed successful representations of former Trump CFO Allen Weisselberg, former Trump COO Matthew Calamari, Sr., as well as his son, Matthew Calamari, Jr. Can you discuss those representations in greater detail now, as I think you no longer represent them? What was most important to you about your work representing Weisselberg? You’ve mentioned his age and grandchildren as motivating factors for you.

NG: With respect to Allen Weisselberg, he’s one of those guys who, once you get to know him, he’s impossible not to like and respect. Not that he didn’t make mistakes, which he admitted to by pleading guilty, but given his age, health and the nature of the offenses with which he was charged, he shouldn’t have been put through that ordeal. Unfortunately, we all know why he was. He was textbook collateral damage. Watching his wife, sons and grandchildren rally to support him through those difficult eight months, from the day he plead guilty to the final day of his 100-day sentence, was a beautiful thing. Allen is blessed with a wonderful family.

My representation of Trump Organization COO Matthew Calamari and his son, Matthew Calamari Jr., the company’s Director of Security, was much less dramatic, but also successful. My job on their behalf was not that difficult because neither did anything unlawful. My team made a compelling case demonstrating actual innocence on behalf of Matt Sr., and the DA’s Office declined to pursue charges. Matt Jr. was given complete immunity and testified before the grand jury. The Calamaris are another wonderful family.

LD: What was it like threading the needle between prosecutors who very much wanted Weisselberg to testify against Donald Trump and his refusal and or truthful inability to do so. Is that the most difficult balance you’ve had to strike as a lawyer?

NG: The Weisselberg case was probably the second most tricky criminal case of my career. And, as you know, in 38 years of practice, I’ve dealt with more than my fair share of tricky matters.

Never before have I had a witness prepared for his trial testimony by both the prosecution and defense. It was a difficult needle to thread, but because I worked with attorneys on both sides of the case who possessed the utmost skill and integrity, we got the job done. I just can’t say enough about the professionalism of Trump Organization defense counsel, Alan Futerfas, and the District Attorney’s lead prosecutor, Susan Hoffinger. The judge was also a man of his word.

LD: So, you know I have to ask. What was the trickiest criminal case if the CFO of a former President’s private company is the runner-up?

NG: Without a doubt it was the arson case I tried in 2000. I represented a young boy who, after 18 hours of intense interrogation, falsely confessed to starting a fire at a Brooklyn stable that killed 21 horses. The trial was complicated and even interrupted right in the middle by the tragic events of 9/11. I remember it like it was yesterday.

I brought my mother to court that day because she wanted to watch me cross examine a few witnesses. I remember being somewhat perturbed when the clerk told me trial was going to be adjourned that day because a plane had flown into the World Trade Center, traffic was a mess and some jurors would likely have trouble getting to the courthouse. At that point, knowing nothing, I thought we should have waited to see if all the jurors arrived and, if so, plowed forward. I figured that someone flying a private plane probably had a heart attack.

It wasn’t until I got back into the car with my mom and turned on the radio that I realized the situation was much more serious. A second plane had hit the towers, but I still didn’t fully get it. I remember hearing on the radio that a tower had collapsed. I told my mother “a tower couldn’t have collapsed, they must mean there’s a fire and a few pieces of the building are falling off.” It wasn’t until I got home and turned on the television that I truly realized what was happening.

The Weisselberg case was probably the second most tricky criminal case of my career. And, as you know, in 38 years of practice, I’ve dealt with more than my fair share of tricky matters.

The interruption of the arson trial because of 9/11 presented a logistical challenge, but that’s not why the case was tricky. The case was tricky because, during the course of my client’s marathon interrogation, he volunteered – completely on his own – to take a lie detector test to prove his innocence. The police then gave him a polygraph test in the middle of the night and, after conferring privately with the examiner, told him he had failed. They also told him that, because he had failed, no jury would ever believe his denial or alibi once jurors learned that he had failed the polygraph. Naturally the boy, who was 17 at the time he was interrogated, had no idea that polygraph results are inadmissible in court. So he made up a story about being at the stable that night and confessed to having started the fire by accident. That “confession” was false for several reasons, including because he was nowhere near the stable that night and because incontrovertible evidence demonstrated that the fire was set intentionally.

At the first pretrial conference, I told the prosecution, in open court and on the record, that I intended to introduce the polygraph data and results into evidence at trial. The judge at the conference, who did not end up being the trial judge, snidely asked me how long I had been practicing law. What they didn’t know was that I had already sent the polygraph evidence to one of the country’s foremost polygraph experts, who lived in Alaska and trained Secret Service polygraph examiners, and he had concluded definitively that my client had passed the polygraph with flying colors.

Although there was nothing unlawful about the police lying to a suspect under interrogation – even about the results of a polygraph test – the expert’s trial testimony helped the jury understand how my client had been tricked into giving the false confession. Indeed, my client testified that, once the police convinced him that he had failed the test and that it would be damning evidence if he went to trial, making up a story about having started the fire accidentally seemed like his best option. The expert testimony, my client’s testimony, and the testimony of several alibi witnesses, all of which was corroborated by a complicated set of beeper and cellphone records, led to a unanimous not guilty verdict in less than two hours.

LD: From a 10,000 foot level – or perhaps an historic perspective – how do you think the litigation involving Donald Trump will be seen? And what was it like as a lawyer having a part in this rather unbelievable series of lawsuits and prosecutions?

NG: I think that we will look back at these politically motivated prosecutions, as well as the weaponization of our criminal justice system, as one of the darker chapters in our nation’s history. It needs to end – on both sides of the aisle and once and for all – so we can all get back to focusing on the real problems facing our country. Convicting Donald Trump or Hunter Biden is not going to help our nation’s problems with immigration, poverty, homelessness, or our difficulties with China.

LD: Can you remind our readers of your work representing Hunter Biden? I believe he was sued in connection with the purchase of a hedge fund?

NG: Sure. Many years ago, I represented Hunter in a lawsuit alleging that he and his uncle, James Biden, who is President Biden’s brother, had perpetrated a complex financial fraud in connection with that deal. There really wasn’t any evidence to support those allegations and, without boring you with legal details, I was eventually able to have the case dismissed. But even way back then it was interesting to see how national politics could impact the legal system.

At the time that case was filed, Joe Biden was running for president. For that reason, the plaintiff and his counsel clearly believed they had Hunter over a barrel. They believed that his family, particularly his father, would be anxious for him to settle. Boy, were they wrong!

The expert’s trial testimony helped the jury understand how my client had been tricked into giving the false confession.

I started defending the case vigorously and Hunter refused to pay anything – not a cent – to make the case go away. Then, a funny thing happened. Joe Biden dropped out of the presidential race. And suddenly, the case went dormant – nothing happened for month after month. Quite clearly, the plaintiff lost interest because he believed he had lost his leverage. And, it wasn’t until Barack Obama won the Democratic nomination – and Joe Biden was picked to be his running mate – that the plaintiff rose from the dead and the case came back to life. Of course, the court saw through it and knew exactly what was going on. The reincarnated case was soon dismissed.

LD: At one point, I believe, you were simultaneously involved in representing Mr. Weisselberg and Kanye West. I assume that’s something that law school didn’t prepare you for. The ability to handle the media aspects of high-profile cases has become a key tool for lawyers. What are some of your lessons as a lawyer who’s respected both for your courtroom skills and your ability manage the media?

NG: You are indeed correct that, in high-profile cases, the ability to deal with the media is often essential, both for protecting clients and for advocating on their behalf. To my knowledge, law schools and even law firms with robust associate training programs typically neglect this area of advocacy. There are many lessons to be taught about interacting with the media.

First, never treat the media with disrespect. Just like lawyers, journalists have a job to do. The overwhelming majority of journalists are ethical and professional. Even when you can’t talk about a matter, return a call and explain why, rather than simply ignoring an inquiry. Recently, notwithstanding voluminous documents my team reviewed and many interviews we conducted in a particular case, I learned a critical piece of information from a reporter while returning her call about a completely unrelated matter. Dealing with the press is not always a one-way street.

Second, lawyers have to learn how to speak to the press. I’m amazed at how even some experienced practitioners don’t understand the difference between talking “off the record,” “not for attribution,” and “on the record.” Many lawyers don’t understand that the ground rules in dealing with the press are negotiated in advance and can sometimes change, even on a question-by-question basis, during the course of an interview.

Third, when alerted to a damaging story the press is prepared to run about your client, a lawyer has options. If the allegations to be reported are demonstrably baseless, point that out to a reporter and explain why. Respectable journalists would rather kill a story than run a potentially inaccurate story. Even when a negative story can’t be killed, it can often be balanced.

Finally, although it takes considerably more skill and experience, at times you can generate a story that is helpful to a client – and their legal situation – when there are non-confidential, newsworthy facts you can bring to the attention of a trusted journalist.

LD: For a moderately liberal Brooklyn Democrat, you’re finding yourself involved in some pretty intense Conservative circles. Is that a reflection of where we’re at in this country in terms of the legal system’s role in a time of great divide?

NG: My so-called “involvement” in conservative circles is overstated and simply a matter of coincidence. I don’t consider any of my cases to be political in nature. Once I agree to take on a case, my client’s politics are irrelevant to me. I take on only a small percentage of the cases I am offered, but a client’s politics have never been a material factor in deciding which to take on. And I believe that’s been borne out throughout my career. Many lawyers would not have represented senior officers of the Trump Organization. Many would not have represented Hunter Biden. But I enjoyed the challenges in each of those matters. I’ve never had a second thought about taking any of them on.

I think that we will look back at these politically motivated prosecutions, as well as the weaponization of our criminal justice system, as one of the darker chapters in our nation’s history.

LD: How’s it going as co-head of Global Litigation and head of Commercial Litigation at Cadwalader? The firm seems to be developing great depth in its trial bench.

NG: Our Litigation Group at Cadwalader is truly on a roll. I think we’re the busiest group at the firm right now. Over the 30 months I’ve been here, we have added key lateral partners, key lateral associates, as well as promoted from within. We are rapidly growing in size and stature, but are being careful to grow responsibly.

The types of matters our litigators take on continue to diversify, as does our client base. Younger partners are being mentored in the art of hunting as more and more clients are retaining the firm for the first time – solely for our litigation capabilities. We’ve had a staggering number of trials over the last few years. We have more on the horizon with over a half dozen scheduled to go in the next year. We have a rapidly deepening bench and many young partners on the cusp of becoming first chair trial lawyers.

It’s been exciting to watch us grow, but the real exciting thing is that it’s going to continue. We continue to promote the best and brightest from within. We continue to recruit and hire top lateral associates in key areas. And we remain interested in meeting lateral partner candidates whose practice is consistent with our strategic plan. For litigators, there’s never been a more opportune time to join Cadwalader. Our commitment to growth presents unparalleled opportunities.

I’ve had a lot of fun over the last 30 months and I’m proud of what we’ve accomplished. My Co-Head of Global Litigation, Jason Halper, got the ball rolling long before I arrived. We are both fortunate to have the strong support of our transactional partners, who are equally committed to growing the firm’s litigation practice.

LD: What are you looking forward to this summer?

NG: To be honest, a little peace and quiet – particularly after how busy I was last summer. But just when I thought things would finally slow down, several new opportunities I couldn’t pass up came out of the woodwork. I was recently retained to serve as an expert witness for the first time in my career. Giving that expert testimony was a challenge I really enjoyed. More recently, I was retained as a party arbitrator for the first time. No matter how much you think you’ve learned in this profession, there’s always a lot more to learn. I enjoy the fact that new opportunities are always coming at me from different, unexpected directions.

LD: How has your work-life schedule adapted to the post-Covid era? I find it interesting that you and other high-powered lawyers are working from home more than ever before and have adapted to that approach successfully.

NG: Post-Covid protocols have been tricky to implement, but our firm has done a nice job balancing the competing interests. People are not required to work in the office as often as they used to be. And many lawyers have used their increased work-from-home opportunities to increase efficiency and better balance their work and personal lives. But particularly for younger lawyers who want to learn quickly, there is no substitute for being in the office and taking advantage of the impromptu mentoring opportunities presented on a daily basis. Despite my difficult travel schedule, I try to be in the office as much as possible. I enjoy interacting with younger partners and associates eager to learn about how to best serve the firm’s clients.

LD: How’s the family?

NG: Doing incredibly well, and thanks for asking. Jackie and I are proud of our three sons and the paths they are now on. One of my 21-year olds is interning for Mayor Adams for the third straight summer. He loves what he’s doing and will graduate from Fordham next year. After talking for years about acting and writing screenplays, our other 21-year old took a single law class in college. Now he is interested in juvenile justice and thinking about law school. And our little guy, who just graduated from high school, is excited about starting college at Bucknell next month. As a parent, you spend countless, sleepless nights worrying about your kids. Then, all of a sudden, sometimes things just seem to fall into place.