As told to Hon. Elizabeth S. Stong and Mauricio Videla, Esq.[1]
Have you ever wondered how someone who has a dream job—say, for example, general counsel of a Major League Baseball team—got to that position? Or what kinds of leadership lessons they learned along the way? Matthew J. Shuber, General Counsel and Senior Vice President of Legal Affairs for the Toronto Blue Jays, shares his thoughts and reflections on this subject with the ABA Business Law Section’s Leadership Development Committee, in conversation with past Chair Hon. Elizabeth S. Stong and Mauricio Videla, Esq.
ESS/MV: So, how do you get to be general counsel of a Major League Baseball team—a dream job in the eyes of many lawyers (and sports fans)?
Matthew Shuber: This is a natural question to ask and one that I am asked frequently. And if I simply respond directly to it, then it tells a story. Is that story one with a lesson in it? Perhaps, but not the one people might expect. So, my guidance to everyone is that if you wish to become general counsel in professional baseball, the surefire steps to take are as follows:
- Join a band and write and perform music, in high school and into college. Optimally, you should also deeply immerse yourself in recorded music and attend a lot of live music concerts.
- In college, focus initially on computer science and mathematics.
- Then, midway through college, change directions entirely, moving away from science and math—and next, head off to law school.
- Midway through law school, dive into a broad range of different substantive areas of the law, and perhaps develop a bit of a specialty in criminal law.
- After your second year of law school, work at one of the big national law firms, with a focus on litigation, with particular emphasis on drug patent litigation.
- When you complete law school, pursue a career in criminal defense work. Be sure to work with a wonderful group of uniquely intelligent and thoughtful lawyers, on complex and interesting cases. If they are high-profile matters, so much the better.
- Keep assessing your choices—and after about three years, move on from private practice and . . . this part is critical . . . do so without a clear plan for your next position, or even your next step.
- Pursue an odd and unexpected business opportunity with friends, developing skills in sales and negotiation. Be sure that the business doesn’t ultimately generate substantial revenue, and that it comes to an end on its own.
- Through networking and some number of events—some random, and others less so—be invited by a professional baseball team to interview for a job that you never applied for.
Of course, I say all of this in jest. The point is that this is only my path. And if I were to try to draw some lessons from that path, it’s that there is no single set of decisions or experiences that definitively lead to a legal or business affairs job in sports. Rather, like many things in life, there are many factors that come together to create any particular outcome. With hindsight, you can see how each experience may have led, one way or another, to the next. I try to advise young lawyers that, while a goal or direction is always a good thing, perhaps equally important are the skills and opportunities that present themselves along the way—and you never know for certain where they will lead, but you can be pretty sure that they will lead somewhere interesting.
ESS/MV: Tell us something about you, or your path, that has made a difference, and that does not come up in your “official” bio.
Matthew Shuber: On the one hand—to state something that is entirely obvious—I’m a product of my training and work experience. Even though I did not ultimately stay in criminal law as my field of practice, I was immersed in the representation of clients in unique and complex matters, exposed to novel concepts and theories, and—probably most important—worked on a close-knit team with great, motivated, highly intelligent people. Those people influenced my work ethic and substantive skills, certainly, but they also challenged me, trusted me, and demonstrated how to maintain core values despite outside challenges.
On the other hand, a great deal of what I’ve done in my commercial legal–general counsel–business leadership role has, in all honesty, been self-taught—or perhaps more accurately, developed through the process of challenging myself deeply: to seek out learning opportunities, to question my own work and decisions, and to continually look to grow and improve.
ESS/MV: What are one or two skills that are especially useful for success in the business of law?
Matthew Shuber: One skill is the ability and willingness to dig deeper—deeper into the project that you are working on, for sure, but really what I mean is really investing in every facet of the work, including the environment in which it is taking place; the processes and norms that affect the work; the people with whom you are working and the people you are negotiating with; and your goals for the relationships or arrangement that you are working to establish. And don’t overlook the more nuanced / less obvious factors that may affect all those details.
When I express these things, I wonder if they sound a bit trite. But in my experience, they are not trite at all. Many people, even very intelligent and hardworking people, tend to stop at a particular point and either assume they know “enough” to complete the task, or that there is some kind of known limit that exists beyond which the return on investment isn’t justified. My experience is different. I’ve found that when you challenge yourself to develop a real understanding of all the components of the task, then you become far more comfortable building on that knowledge in the future. And it allows you to invest in your own continual improvement over time—and you’re worth it.
As a real-world example, businesses negotiate commercial services agreements every single day. It’s possible to negotiate some of these agreements with only a limited understanding of the specific services and, if the services are good and useful, the central goals will be achieved. But for myself, I’ve always found that I will do a better job, and get a better result, if I know as much as possible about the services we are negotiating about. I’m determined that when I conclude a negotiation or sign a contract, I should be able to understand and explain it—and anyone else who reads that contract should also be able to do the same. The benefit of this is that then the contract can truly be tailored for risk allocation and responsibilities with precision. And beyond that, as the parties continue to work together, they will have a clear document—and an effective roadmap—going forward.
Here is another real-world example: take the time to learn from the subject matter experts with whom you come into contact and collaborate. I am at my best when I have knowledgeable and capable people to partner with on the team. I always remember the people from whom I have learned the most. And I’ve seen that the best projects, negotiations, and results of my career have been in circumstances of true collaboration and knowledge-sharing.
ESS/MV: What is the best—or worst—piece of advice that you have ever received?
Matthew Shuber: That’s a good question. The best piece of advice is “there is always a place for someone who makes themself indispensable.” I view this as another way of saying that what matters is what you invest in and contribute. Put another way, it’s advice along the lines of “in each situation and with each opportunity, do the very best you can and don’t spend time or energy thinking about what you get back for it.” I’ve found that following that advice always leads to developing new skills and knowledge, and to new pathways that might not have existed or been visible previously.
The worst piece of advice I’ve ever received is “if you find something you’re good at, stick with that.” If I had followed that advice, I would have stuck with criminal defense work. I was at a good firm, with good people, doing interesting and challenging work. But something inside me told me that there were other paths that I could pursue that I might connect with more deeply and sustainably. And I let myself take that chance. I’m glad I did.
ESS/MV: Staying with advice, what advice would you give your twenty-five-year-old self?
Matthew Shuber: To begin, the possibilities are endless! It’s okay not to know precisely where you will be in five or ten years. At twenty-six, I had already been called to the bar, and I was about to start what I thought would be my career, in criminal law. This may seem contradictory, but I think it’s possible both to be committed to a career (and investing deeply in that career to build skills and relationships) and to be open to the fact that, at some point, you may wish to change directions.
ESS/MV: As you have taken on greater leadership roles in your career, and especially now as general counsel, how has your mindset changed in order to meet the demands and expectations?
Matthew Shuber: Honestly, I’m not sure that my mindset has changed at all. At the core, one of my guiding principles has been to evaluate decisions, plans, arrangements, processes, and opportunities against what is best for the organization (as opposed to any particular person or department), and over the long term (as opposed to a short time frame). I’m thankful to be part of an organization that also values long-term, sustainable thinking and decision-making. And while the external demands and expectations may have evolved, I expect a fair bit of myself, and so those external factors haven’t really changed my way of thinking.
ESS/MV: There’s a saying that “leadership is often baptism by fire.” Tell us about a particular significant or memorable business decision or challenge that you confronted and how you approached it.
Matthew Shuber: I would point to the role I had the privilege to play in connection with our Spring Training facility / player development complex in Dunedin, Florida. These facilities are a unique element of Major League Baseball—as a business and as a sport—to say the least, and that is even more true for the Blue Jays as the lone Canadian team.
For obvious reasons, Spring Training facilities projects don’t happen frequently, and when they do, they are made up of a myriad of different discussions, decisions, and factors, each of which is individually complex and challenging. The tasks include financing, working with multiple levels of government, construction and design, internal organizational needs, and more. And while this was a group project, within that group, at particular times I needed to take on various leadership roles and rely on persuasion as opposed to positional authority or direction. I probably learned as much from that experience and opportunity as from any other in my career.
ESS/MV: We have to ask—what’s your “superpower”?
Matthew Shuber: Well, I could say that I have two: neuroticism and self-doubt. I’m being silly, of course. Those aren’t really things I suffer from, but there’s still a nugget of truth there, in that I think we all feel sometimes that we don’t have all the answers.
To be serious, perhaps my “superpower” is my inability to kid myself. If something looks and feels a certain way, then even if there may be outside pressures to ignore that assessment, I simply can’t go there. I ultimately feel driven to tackle reality, even when that reality is unpleasant or seemingly challenging. And I don’t say any of this in any kind of judgmental way. I understand why some people feel that they are facing binary decisions and that they don’t have choices—for example, that either a project or plan must go ahead immediately and without full consideration, or it just won’t be able to go ahead at all.
My experience and approach are more along the lines of “if it’s worth doing, it’s worth doing well.” Not perfectly, mind you, because there’s usually no such thing. Just well. And as I’ve said, I do believe in long-term thinking, so I’ve seen that spending a little more time and energy at the outset pays dividends over time.
ESS/MV: Sometimes a young—or not-so-young—lawyer may find themselves as the only person like them in the room. What tips would you share to deal with that situation?
Matthew Shuber: Honestly, I feel that a mindset that focuses on being the “only” has the potential to be self-limiting. I recognize that there are situations in which people are, in fact, the “only”—there is a reality to that lived experience.
But I think it’s far more productive to take the mental and emotional step that’s needed to emphasize the “in the room” portion, instead of the “the only” portion. That is, once you are in the room, it’s critical to recognize that first, there’s a reason you are there and second, being in that room presents an opportunity. So, own it, try to make a difference by your presence, and don’t limit or sabotage yourself!
Postscript
ESS/MV: When we met, at our Leadership Dialogue program in Toronto, the Blue Jays were in the final weeks of the regular season. Over the course of working on this article, they defeated the New York Yankees in the Division Series and won the American League pennant after an epic matchup with the Seattle Mariners. The World Series between the Blue Jays and the defending champions, the Los Angeles Dodgers, was one for the ages, with the Dodgers ultimately winning Game 7 of the World Series by the slimmest of margins, and then only after 11 innings. I’m sure that the experience of the last six weeks has been something special for you, and I’d be remiss if I didn’t ask you if there are any reflections that you would like to share.
Matthew Shuber: Thank you for asking that. This experience truly has been like no other, and not simply because of the obvious accomplishments of the team on the field. Although the final result wasn’t what any of the Blue Jays players, front office personnel, or our incredible fans would have hoped for, the more I reflect on the experience, the more I’m struck by something even more important than a championship trophy.
Sometimes, in sports and in life, you lose. Although it stings, you know there were specific reasons for the loss and that there was more to do. And so you look to learn from the experience and get better as a result. This experience has been a little bit different. I believe—actually, I know—that everyone in the organization, on and off the field, did all that they could and that we are second to none, whether or not that shows in the final score or the record books.
At this moment I’m struck by the fact that so many people saw—and were moved by—the character, resilience, and fellowship of the Blue Jays players. More than one person has observed and commented to me that this was truly a team, in a way they’ve never seen or experienced before, in any sport.
That makes me enormously proud, because I know that what those people are seeing isn’t an accident. The characteristics of the group of players that competed on the field this October reflects and exemplifies the values and approach of the Blue Jays organization that exists off the field. And I know from many years of working in professional sports that it is hard enough to establish those things in a front office, let alone to have the commitment to do so on the playing field. But our organization has that commitment—and it showed. And it resonated with people. To me, that’s something to be proud of, because in some ways, it’s the most meaningful outcome possible.
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This article is related to a CLE program presented at the ABA Business Law Section’s 2025 Fall Meeting titled “Leadership Defined: A Fireside Chat with Matthew Shuber, Senior Vice President of Legal & Government Affairs and General Counsel of the Toronto Blue Jays (MLB).” For further information, view the program materials.
Matthew J. Shuber is Senior Vice President, Legal Affairs and General Counsel of the Toronto Blue Jays Baseball Club (Major League Baseball’s only Canadian franchise) and for Rogers Centre stadium. Hon. Elizabeth S. Stong is a U.S. Bankruptcy Judge for the Eastern District of New York, sitting in Brooklyn. Mauricio Videla, Esq., MPA, is a Banking & Financial Services Counsel and Securities Arbitrator. Judge Stong and Mr. Videla are active in the leadership of the ABA Business Law Section and its Leadership Development Committee. ↑
