For Matthew Schwartz, part of the lure of private practice was the “three-dimensional chess” required to represent real people and companies. At this point in his career, it’s safe to say that the former prosecutor has mastered the game. Schwartz has done so at storied litigation firm Boies Schiller Flexner, which he joined in 2015 after nearly a decade serving as an Assistant U.S Attorney for the Southern District of New York. No stranger to high-profile litigation, Schwartz spent years leading the investigation into the infamous Bernie Madoff Ponzi scheme case. He is a three-time recipient of the Justice Department’s prestigious John Marshall Award.
At Boies Schiller, Schwartz quickly became a pillar of the firm’s white-collar practice, handling a wide range of complex matters for clients like Red Granite Pictures (in the government’s $1B civil forfeiture action), AIG and DraftKings – along with many clients he has successfully kept out of the courtroom. After a few short years, Schwartz joined the firm’s executive committee and became a co-managing partner in early 2021.
Lawdragon: Tell me about your career path, from private practice to Assistant US Attorney to private practice again. How did that happen?
Matthew Schwartz: Following law school, I briefly worked at a large international law firm, which was fine, but was probably not for me at that point in my career.
LD: What about it wasn't for you? The size?
MS: Yes. I'm always someone who has appreciated learning by doing, and so the opportunity to get my hands dirty by being in a courtroom actually handling cases was very attractive.
That said, coming out of law school, I had no idea what I was doing. So, the first thing that I did was fix a mistake that I had made in law school, which was not appreciating the value of a clerkship. I reached out to any judges who might be hiring, and I was very fortunate that there was a judge in the Southern District of New York who had an opening.
That totally changed the arc of my career. I spent a year and a half clerking in district court, watching all varieties of matters: civil, criminal, big matters, small matters, great lawyers, terrible lawyers — all of which are important to see when you're a young lawyer. I then spent a year clerking in the Court of Appeals.
When I was ready to start practicing again, I was looking exclusively at government opportunities. I knew that I wanted to represent the government in federal investigations and litigations and really be in the courtroom. I was lucky to be hired as an Assistant U.S. Attorney in the Southern District of New York and stayed there just shy of a decade.
LD: What led you to Boies Schiller specifically when you moved to private practice?
MS: One thing that I really enjoyed about working in the government was the incredible autonomy that prosecutors have. I wanted a firm that was going to trust me as much as the government trusted me. And that's how I ended up at Boies Schiller.
The firm has a unique combination of representing the biggest clients and matters, while simultaneously affording its lawyers the freedom both to handle their business and their client's businesses in a way that is maximally effective.
LD: Were there any shifts from the U.S. Attorney's Office to private practice that surprised you or that you found particularly rewarding?
MS: Sure. I mean, being a government prosecutor has a real clarity of mission to it, right? In some senses it is a simple job. You investigate the facts, and if they support bringing a case then you litigate the case.
MS: Being a lawyer in private practice is much more multi-dimensional, because you’re representing actual people and companies. You have to not only chart a winning legal strategy, but do that while navigating business concerns, public relations, investor relations, and all sorts of other aspects, some of which may be much more important or threatening to the client than whatever the case is that you’re handling. And, of course, you have to do it all within a budget.
That sort of three-dimensional chess is what attracted me to private practice. It’s just an experience that doesn't exist in the government, that one can only get by representing people and companies that exist in the real world.
LD: Absolutely. And then moving to today, what kind of cases are you working on right now?
MS: My practice is mostly government investigations, government litigation (either criminal or civil enforcement), and then some purely civil adjuncts to that, especially on behalf of victims pursuing claims against criminals.
I have a very heavy trial schedule right now. In October, I secured a win in a case where I was representing a private equity firm against the Federal Trade Commission. The Federal Trade Commission charged a company in which my client invested with running a fraudulent, deceptive business. They also sued my client, the private equity firm. We argued that you can't hold an investor liable for whatever one of their portfolio companies does. In fact, the FTC’s approach is dangerous to business and, if successful, would have chilled investments, especially startup investments. So, we thought it was important to take a stand. We had a series of wins in that case, culminating in the judge granting our motion for judgment after the FTC rested its case at trial.
I have a white collar federal criminal trial scheduled in January, and then in February I will be trying a long-running civil case in which I represent a foreign bank that was defrauded of billions of dollars by its former Chairman.
I was also recently retained to represent an individual who was criminally charged in a case whose lead defendant was the head of Donald Trump's inaugural committee. They were charged with being unregistered foreign agents of the United Arab Emirates. So, that's a significant criminal case that is just heating up.
But, really, some of my biggest wins are for clients where we successfully convince prosecutors or regulators not to bring charges in the first place.
I can't talk about those cases by name, but in a lot of ways they're the most satisfying. It's always nice to get a jury verdict, but when you can stop the problem from getting out of hand in the first place, that's very rewarding.
LD: Right. I believe I read a quote from you saying that if you're doing your job right, you're trying not to get in the courtroom.
MS: That's right. Depending on the stage of a case when I’m retained, that’s right. When I’m hired early in an investigation, the goal is to convince the government one way or the other not to bring a case. Of course, I’m often hired after charges have already been brought, and in those cases clients are usually looking for me to be in the courtroom with them.
LD: Looking back at trials in your career overall, are there any that stand out in your memory as either being the most interesting or complex to work on?
MS: They're all rewarding in different ways, but the Bernie Madoff trial, for example, was a mammoth endeavor. I mean, we were unraveling decades and decades of fraud.
LD: How long were you working on that?
MS: I was working on the case for five or six years, first as part of an incredible team of lawyers, agents, and other professionals, and ultimately as a leader of that team. The trial itself lasted about six months. A six-month-long, incredibly complicated jury trial.
LD: I'm sure.
MS: It was rewarding to be able to communicate to a jury this hugely complex material. We got into the actual computer code that was written to perpetrate the fraud. I mean, very, very nuanced evidence.
That said, it's also extremely rewarding to handle small cases for real people who see tangible results. As a defense lawyer, helping someone exonerate themselves after they’ve been falsely charged with wrongdoing is incredibly gratifying.
I handled a case where the government had charged my client with securities fraud and conspiracy. There was no doubt in that case that a fraud was perpetrated, but my client wasn't a part of it. He was used by the fraudsters.
We tried the case for a month and the jury returned a guilty verdict, which was incredibly disappointing. But then, in a first for my career, the judge threw out the verdict and said that we had demonstrated that there were grave concerns that my client was actually innocent.
Giving that news to my client, knowing not just that he wouldn’t potentially have to go to jail, but also that he could tell his parents, his wife and his very young children that the judge had understood that he was innocent – that was one of the most rewarding moments of my career.
LD: I can imagine. I feel like people often forget about the very human aspect of financial litigation.
MS: Right. I love representing big companies, but it is also important to have a well-rounded practice. Representing individuals has a different, much more personal aspect to it. It also allows me to have deeper and more frequent interactions with the government, which benefits all of my clients.
LD: Absolutely. And then, outside of your trial work, you were recently made a co-managing partner at the firm, as well. How did you enter that role?
MS: I had been informally involved in various aspects of management previously, and then in early 2020 I was put on the firm-wide executive committee, which is kind of like our board of directors.
And then, at the start of 2021, I became one of the managing partners of the firm. With that, I’m involved in the day-to-day management of the firm, which is a lot of the mundane logistics that are necessary to make an organization work.
Earlier I mentioned the culture of our firm, with great cases, great clients and incredible freedom to our lawyers. As managing partner, I view myself as a custodian of that culture. I help take care of the logistics so that our lawyers can concentrate on doing what they do best, which is representing our clients and doing impressive work.
LD: Moving back to the courtroom a bit, what is your style as a lawyer?
MS: I think the most important thing is to be kind of true to yourself in the courtroom. For some people, that means being an absolute pit bull — yelling and getting in witnesses' faces. Sometimes juries love that if it is genuine.
That's not me, though. I tend to be a lot more methodical and even keeled. But that doesn't mean that I don't go in for the kill when necessary. I just do it with a sharp knife, not a loud gun.
LD: I can imagine that having to explain very complex financial concepts to juries must require a lot of careful methodology, as well.
MS: It does. And the trick, especially when you're talking to a jury, is to do it in a way that is both true to the facts, but not so detailed and so boring that you lose them.
I mean, talking to a jury is a very artificial way of talking to people. They have no ability to ask you questions, they have no ability to ask you to repeat yourself and you’re not necessarily presenting information to them in a logical order.
So, I think about it like making a movie. In film you have to capture different shots individually and then cut between them in the final version. So, it's the lawyer’s responsibility to make very clear to the jury where we are going and what the finished product is going to look like. That way, they understand what they’re hearing as the evidence comes in and are able to tie it together in a way that makes sense to them. That clarity of purpose needs to come from the opening statement.
LD: That’s great advice. Do you have any other pieces of advice you’d give early-career lawyers?
MS: I would say two things: one about the practice of law, and one about the business of law.
For those who want to be trial lawyers, spend as much time in a courtroom as possible. There's a big difference between taking an evidence class and actually having to go through the process of admitting a piece of testimony or documents into evidence. Do so as a law clerk early in your career, if you can.
But don’t forget, you can also go to court as a spectator. Courts are open. You can go down there and just watch. That's incredibly valuable because, again, watching other attorneys makes it clear that there isn’t one way to be a lawyer.
So, I think that's number one, but number two – the business side of law – is to maintain all of your relationships. Be good to people, whether they’re your colleagues or your adversaries. At the end of the day, we're all doing the same thing.