In this episode of S&C Sidebar, Jake Croke, Co-Head of S&C’s Corporate Governance Litigation Practice, is joined by Litigation Partner Andrew DeFilippis to discuss how Andrew’s experience working as an advisor to the Secretary of Homeland Security, as a federal prosecutor and at S&C has given him a practical perspective on advising clients in high-stakes matters, especially where government enforcement, compliance and litigation intersect.
Andrew emphasizes the value of translating complex legal and regulatory issues into clear, practical advice for clients, particularly in fast-moving areas where national security concerns increasingly affect corporate compliance.
Full transcript below.
Jake: Welcome to S&C Sidebar. I’m Jake Croke, partner in Sullivan & Cromwell’s Litigation Group and Co-Head of our Corporate Governance Litigation Practice.
Today, it’s my great pleasure to be joined by Andrew DeFilippis, a partner in S&C’s Litigation Group and a member of National Security and Criminal Defense Investigations Practice. Andrew’s career has taken him to the Department of Homeland Security, to S&C, to nearly a decade as a federal prosecutor in the Southern District of New York and a Main Justice, and then back to the Firm.
Today, Andrew advises clients on a wide range of critical issues at the intersection of national security, white collar enforcement, international trade and all manner of complex litigation. Andrew, welcome!
Andrew: Thank you, Jake! Great to be here.
Jake: So, Andrew, you’ve seen high-stakes legal problems from several very different vantage points: inside a cabinet department, during your first stint at S&C, as a prosecutor, and now again back at the Firm. Having seen things from all those angles, how does that affect the way in which you approach issues for clients?
Andrew: Well, Jake, I think there’s inherent value in having been on both sides kinds of problems and issues that we confront with our clients, whether it’s an internal investigation or a regulatory issues, there’s a lot of value in being able to tell a client that not only have you dealt with the government on these kinds of issues, but that you’ve been on the other side. And so, just to cite a few examples, as we advise clients on tariffs and customs laws, it’s valuable to be able to bring perspective having been at a department like Homeland Security which oversees Customs and Border Protection. And then of course in big corporate white collar investigations, in other internal investigations, to have the perspective of somebody who’s prosecuted criminal cases and corporate criminal cases, is really valuable and I think something that informs everything I do, no matter what matter I’m advising a client on.
Jake: And during your time as a prosecutor, I know you were involved in a wide range of very high profile matters, which included conducting eight lengthy trials. In a trial, one of the key challenges is that even the most complicated investigation ultimately has to become simple incredible stories supported by evidence. How is that particular experience coming to play for you in a day-to-day practice?
Andrew: Yeah, Jake, I mean I think having done a number of jury trials, the skills that you learn in presenting a case to a jury are very valuable and important in advising clients. And one of those key skills I think is boiling down a complicated legal issue into a bottom line conclusion or recommendation that someone who is not as immersed in the details of the law or the facts as you are can easily understand and make use of. And in the jury context that means you are presenting to people who are not lawyers by and large, and trying to convince them of your view of the evidence and the facts.
In the client context, many of our clients of course and many of our contacts at clients are lawyers, but they’re extremely busy, they’re juggling any number of issues, and so if you’re advising a financial institution on a very tedious regulation or in connection with a litigation issue, you really do need to boil it down, largely in the same way that you would for a jury to give them the bottom line that’s going to allow them to do their jobs and that’s especially important when you’re advising CEO’s and executives who are not lawyers.
Jake: And I think, in terms of how people understand things, when most people hear national security they still think first about terrorism or espionage. You’ve obviously dealt with those issues at the highest level during your career, but some of the national security-related issues in your practice now, include things like sanctions, export controls, customs and tariffs, anti-money laundering rules, and data and digital assets. Is there a common thread running through those areas? And how have you seen the national security framework evolve over the years?
Andrew: Jake, I don’t know if there’s a common thread but there’s certainly common themes or subject areas that we are starting to see more and more as national security issues that come up in the corporate context for our clients.
In the years immediately after 9/11 there was a lot of focus on, for example, terrorist financing and movement of funds by terrorist organizations. But in the years since then, the compliance concerns and the national security concerns have largely expanded to things like flows of goods and supply chains, whether that’s navigating export control laws or tariffs or sanctions. Companies increasingly have to pay close attention to where their goods are coming from and where they’re going to, and whether that implicates U.S. national security.
And another area that’s increasingly prominent is the flow of data. So, for example, the Department of Justice last year implemented a series of regulations that restrict companies’ ability to send bulk-sensitive U.S. data to certain countries of concern. And that’s countries like Iran, China, North Korea and Russia. And so, as companies go about their daily business activities, there are new ways and multiplying ways in which U.S. national security concerns have to be baked in to their compliance programs and their approach to legal problems.
Jake: These are things that I find so fascinating as someone who’s not as close to and who knows most of what I know about this area from the excellent tariff tracker and other publications that you and the rest of the team continue to put out. And it really is something that seems so fast moving where so many clients have questions about what the situation is on any given day. In situations where the governing rules, the enforcement posture and the business consequences are all shifting and clients are dealing with goods that are being moved, contracts that are being signed and time sensitive decisions they have to make, how do you turn an unsettled legal picture into an actual business and legal recommendation rather than just giving a client a long list of potential risks?
Andrew: Well you mentioned the tariffs tracker, Jake, which is a great example and something that I think has evolved in a way that I think that we didn’t expect initially. When we initially had the idea to create tracker charting the various tariffs and tariff initiatives of the Administration it was in the very early days when we had no idea just how many changes there would be to that legal regime over the following year.
And you’re right that half of the battle is really just staying on top of those changes, knowing the various statutory authorities, knowing how they’re going to affect a particular company’s supply chain or imports or business and then being able to synthesize that information quickly, get it to you clients and help them evaluate risk, so I think you are totally right that the challenge is in the national security area and tariffs is a great example.
Things are fast moving and you have to adapt and you have to adapt to not only changing statutory regimes but the use of new or of previously unused statutory regimes like the International Emergency Economic Powers Act which was the statute that the Trump Administration began using for tariffs which no administration had done before. And so it required analyzing the authorities of that law and as you know the Supreme Court struck it down. So all of that is to say it’s been a highly changeable environment and you have to be nimble and you have to at the same time simply and synthesize developments for your clients.
Jake: And you know you take a sort of a step back for a second, one thing that’s always been a great tradition here at S&C is the generalist litigation model. And I know that for you in particular, in addition to all your expertise in national security and white collar related issues and the kinds of things we’ve been talking about now, you’ve also always had a much broader practice and background covering all sorts of complex litigation. How has that broad experience and training helped you when you’re advising your clients?
Andrew: So that’s always one of the things that I’ve loved about S&C is that we focus on the generalist model and we encourage lawyers to, to become involved in matters that aren’t necessarily in their core specialty or their core area of experience and Jake, you and I, back before I had gone to the prosecutor’s office, worked on a series of civil litigations for a financial institution about mortgage-backed securities. And while I was doing internal investigations work at the time, the experience of responding to interrogatories, drafting motions for summary judgment or motions to dismiss, and becoming familiar with that process and with that world, is really invaluable no matter what you’re doing in litigation or in legal practice more broadly. And so I find that many of the cases that start on the side of an internal investigation or regulatory matter ultimately touch on civil litigation issues and other issues where being a generalist is just invaluable.
Jake: Those work. Those were definitely some fund cases. And so notwithstanding the fact that you have this deep substantive expertise across all these different areas, there are always going to be some situations where the facts are just incomplete or uncertain, the stakes are high, things are moving quickly, and a client needs advice. And I know from personal experience, you’re someone with a very well deserved reputation for having excellent judgment and an ability to help clients through those touch situations. What are some of the things that have helped you develop that judgment over the years? What advice would you give to younger lawyers who are learning how to handle these challenging situations?
Andrew: So, I think in my case my experiences in the government both at the Department of Homeland Security and at the Southern District of New York helped give me experience and perspective that really comes in handy in the times of crisis or fast moving situations that you described. As a prosecutor I faced situations where literally a bomb had gone off and we had to investigate the attack and then ultimately prosecute the attack and do a trial in court. Those kinds of situations really prime you to act under pressure and respond quickly to things that literally involve matters of life and death. At the Department of Homeland Security they, that department oversees a wide range of issues and subject areas from immigration to terrorism to emergency response and so in dealing with fast moving situations on the government side it’s given me the skills and perspective to deal with fast moving issues when clients bring them to me. And you’re able to kind of act under pressure, focus on the goal and not get rattled by the time sensitivity or the importance of the issues.
Jake: So, Andrew I think that’s a great place to leave it. Thank you very much for taking the time to discuss today. Thank you all for listening to this episode of S&C Sidebar.
Andrew: Thank you.