The Virtue of the Unexpected Path, with DLA Piper’s Jeffrey Tsai

Jeffrey Tsai’s illustrious, wide-ranging career took shape through a dual mindset: a relentless pursuit of his goals and a willingness to allow shifts in the path getting to them.

The son of immigrants, Tsai was raised on the belief that the U.S. justice system is representative of why his parents – his father, a civil engineer, and his mother, a nurse – came from China, to Taiwan, to America. It’s no surprise that both he and his sister Lisa Tsai ended up becoming litigators. By the time he entered law school, Tsai had a very specific vision for his career: He wanted to serve the country his parents loved by becoming a federal prosecutor.

However, after law school at Georgetown, and after his clerkship, Tsai went through several rounds of applying to U.S. Attorney’s offices before one stuck. But his belief in himself and his ambitions never wavered.

“That process of rejection underscored for me that I really wanted the job, because it’s easy to take a risk, fail and then not bother trying again,” he explains. “The harder thing is to decide that I’m going to rinse and repeat until it works.”

Work it did. Tsai spent five years as an Assistant U.S. Attorney and Deputy Chief in the Southern District of Florida, prosecuting cases ranging from white-collar crimes to sex trafficking cases to homicides. In one high-profile matter, he prosecuted a quadruple-homicide and hijacking conspiracy on the high seas, known as the “Joe Cool” takeover. In the heist, two conspirators attempting to flee the country took over a charter boat – the “Joe Cool” – murdering the boat’s captain, his wife and two crew members before charting course for Cuba. The case attracted national attention and became the subject of a book. “Every action that we took was under a microscope,” Tsai remembers. “I think that was an important exercise to go through as a young lawyer because it really taught me that we should treat every case as the world's most important case, whether it's under the spotlight or not.”

Tsai then moved to D.C., where he served as Senior Counsel to the Assistant Attorney General in the Criminal Division, as well as a trial attorney in the Public Integrity Section. Then, after three years in D.C., Tsai decided he was ready for a new goal: He wanted to move to private practice.

But, again, life had a different plan in place. Tsai planned to move to California to join a law firm but wound up agreeing to meet with the state’s new Attorney General about a job. It was then-AG Kamala Harris.

“After prosecuting public corruption cases out of Washington, I think it’s fair to say that I was jaded about what it means to be a public official,” Tsai remembers. “But in just one short conversation I had with then-General Harris, I was reinvigorated, inspired and ready to ready to run through a wall.”

Tsai was brought on as Special Assistant Attorney General, primarily overseeing Harris’s criminal justice portfolio. Tsai focused on anti-recidivism policy, addressing mass incarceration issues in the state. He and his team created a new division for the Attorney General’s office that developed policies and programs across the state to help local communities, counties and agencies reduce recidivism in practical ways – by identifying jobs, training and education for people who were coming out of the criminal justice system. He also worked on legal policy and cases involving corporate fraud and transnational crime, including negotiating an agreement between five U.S. State Attorneys General and Mexico’s federal government regarding anti-money laundering enforcement and intelligence sharing. 

When he finally did move into private practice, he carried his experience at the California State Attorney General’s office with him. Tsai first launched the State Attorneys General practice at Alston & Bird, and then in 2018, did the same at global law firm DLA Piper. Tsai is now a partner and Co-Chair of the State Attorneys General practice at DLA Piper, concentrating on a wide range of State AG and white-collar criminal defense matters. In addition, in 2022 he became managing partner of the firm’s rapidly growing San Francisco office.

A leader in the office and in his community, Tsai is a planning commissioner in his town, imagining how to address the issues his community will face in the decades to come both in his work and service lives. He also spent years serving as a board member of the Chinese Historical Society of America. Outside of formal organizations, he enjoys being “one of the many” serving a meal or delivering food to community members in need.

Reflecting on how his career has ended up from the way he first envisioned it in law school, Tsai says, “Having a goal and knowing the precise path you’re going to take to get there are two different things. The key is recognizing that the path isn’t always – and shouldn’t be – a straight line.”

That path has taken him through a decade of government service across two states and the nation’s capital, seen him help build leading practices at two high-powered law firms, and usher his current firm’s Northern California office into a new era.

He was right to trust it.

Lawdragon: So, you always knew you wanted to be a federal prosecutor. What was meaningful about that work?

Jeffrey Tsai: That job was one of the single most formative experiences I’ve had in my life. One of the most meaningful parts of being a prosecutor is the opportunity to work on cases big and small in ways that truly help people. The very first thing that I think of from that time is the people we helped in those cases that related to child exploitation, sex trafficking and human trafficking. In those cases, there were discernible, defined victims of crime; we would help young women who were being trafficked, sometimes in scenarios where they did not want our help initially, which to me only reinforces that the nature of that kind of crime is much a physical violation as it is a mental one. For me, working on those cases helped me remember why I wanted to be a lawyer.

I like to be a person who can be relied upon, someone who clients consider to be in the trenches with them. Their problem is my problem, and we're going to work it out together.

LD: Then, tell me about your time in Washington, D.C., as a prosecutor in the criminal division and a courtroom prosecutor in the Public Integrity Section.

JT: That work felt like a wonderful capstone to my time working for the United States. I was able to work on corruption cases and investigations that directly impact communities, but also go to the very heart of what it is as Americans that we consider to be the best part of our country: clean government run by people who only have the public's interest in mind.

LD: How did the move to California came about?

JT: When I finished my time at the Justice Department, I was pretty convinced that my public service had come to a conclusion. But then I came across this opportunity to meet with folks in the California Attorney General's office. I was willing to have discussions about it, but in my mind, I was ready to move on. But I had the opportunity to sit and talk with the new Attorney General, who had been in office a little under two years and was going places. Then-General Kamala Harris.

That was eye-opening in so many different ways. That job was an extraordinary experience for me to grow, not just as a lawyer, but as someone who now dealt with policy related to criminal justice, consumer protection and other issues – to be able to expand my base of knowledge.

LD: What did you learn most?

JT: One of the most important things I learned is the significance of how, as lawyers, we solve problems that sit at the intersection of law, policy and sometimes politics. It's rarely the case that any given legal case we work on is purely an application of cold, black-letter law. It is almost always that plus a consideration of policy issues given the broader impact. And in the context as a private lawyer, it’s also a deep consideration of the business consequences, of consumer consequences, depending upon the kind of case we're doing.

It was that ability to play three-dimensional chess that made me realize that I had previously been playing some form of checkers. I was able to help work on policy related to important, thorny questions intersecting law and policy – things like the reduction of recidivism in this state and in this country, and how recidivism directly impacts how we think about issues of mass incarceration, and how we think about solving the seemingly intractable problem of rising crime, whether it's a violent crime or white-collar crime. You start to see, again, on a very three-dimensional level, just how much the law is only part of the discussion. How do you find a solution that is also at the intersection there? It’s not easy. I do not profess to know exactly how you do it in any given situation, but it's a question that I work on a lot, even in my own capacity as a lawyer in private practice now.

It's rarely the case that any given legal case we work on is purely an application of cold, black-letter law. It is almost always that plus a consideration of policy issues given the broader impact.

LD: Right, so you then you moved to private State Attorneys General practice.

JT: That's right. I could not have predicted after working for then-General Harris that I would take this specific path at Alston & Bird and now DLA Piper. They both, in many ways, came to me by happenstance. Alston & Bird is a great law firm with great lawyers, but after a couple of years there was an opportunity to go to DLA Piper. I had many discussions with Doug Emhoff, Kamala Harris's husband and the former Second Gentleman of the United States. He had just recently moved to DLA Piper. Doug and I started talking, and over time he convinced me that there was an opportunity to be able to expand the work I was doing in the State AG practice and do so on a bigger platform. I will tell you that it’s not a matter for me of going from one law firm to another because one law firm is better than the other. It's because every law firm presents different kinds of opportunities for lawyers.

LD: You've been appointed to leadership roles in the last few years not only in your practice area, but also as managing partner of the San Francisco office. How does that affect your day-to-day?

JT: In some ways, I consider being the managing partner in San Francisco to be the best part of what I do. A leadership job is as much follower as it is leader. At the end of the day, the advancement of our office is built off the individual backs of every lawyer and business professional at our law firm. The managing partner who recognizes all of that work that folks are doing on a daily basis is the one who's going to best be able to advance the interests of that office. Second, I think we sit at at an interesting time in terms of the firm’s future. Northern California and the West Coast generally are significant growth areas for DLA Piper. More and more matters are being brought by regulators on the West Coast. San Francisco, as a result of that, ends up becoming a very important part. We're not just an office here. In many ways we represent the epicenter of how we get the work and how we do the work. So we're always on the balls of our feet, always thinking about how we can kind of push forward. I am so proud to be able to be the person who helps lead the office and be in a situation where I can see everyone else succeed.

LD: Speaking of where things are going from here, can you talk about any current trends you're seeing?

JT: 2025 and midterm elections in 2026 are going to be, I think, two of the most transformative years for this country. As lawyers, I think we're going to see a couple of things. The first is more enforcement than we've seen in recent years. Because of the change in administration, particular State Attorneys General will increase the amount of enforcement they do under the theory that we may see a diminution in enforcement at the federal level. I also think that we will continue to see a number of bipartisan state AG cases that were being brought because of that intersection of joint interest in various kinds of issues that frequently come up, such as opioids and antitrust in the technology sector.

The second is that, in the event we see a healthy improving economy, we're going to see more corporate work. We're going to see more transactions starting to happen. A lot of it will be on the technology side.

LD: We've talked about how getting toward your goal has been a shifting path. What do you find fulfilling about your work now and the path that helped you get there?

JT: The single most enjoyable part of being a private practice lawyer is to be able to have a varying number of clients, all with slightly different interests and requirements. That keeps things interesting for me because I'm constantly having to pivot, grow, adjust, modify, amend what I do, and I find that keeps me going because it allows me to continually grow. I enjoy all the matters I work on because at their root, every single one affects real people, whether it's real people who are in a company who are themselves impacted, or whose consumers are impacted, or it's working for an individual client whose financial life is at stake. I like to be a person who can be relied upon, someone who clients consider to be in the trenches with them. Their problem is my problem, and we're going to work it out together.

LD: You have such an active life in the office and in your community service work – but what do you enjoy doing for fun?

JT: If I'm not playing golf, which I try to do as much as I can, then I'm up here with my family in Lake Tahoe. It is truly God's country. This place here where the focus is on the environment, on connecting yourself to the world you live in, it truly is a wonderful, physical way of replenishing yourself.