Few lawyers have reshaped the world of sports as profoundly as Jeffrey L. Kessler, Co-Executive Chairman of Winston & Strawn LLP. Kessler, recognized as one of the nation’s leading antitrust and sports lawyers, has built a career successfully challenging entrenched power structures in professional and collegiate athletics.
Finding Sports Law by Chance
Kessler did not set out to become a sports lawyer. He explained that his path began “purely by chance” when he joined the law firm Weil, Gotshal & Manges to train as an antitrust lawyer, where one of the firm’s cases at the time was Oscar Robertson v. National Basketball Association, a landmark challenge to restraints on players’ ability to offer their services and skills to the market. The case settled just as Kessler joined the firm, creating a long-term client relationship that led him, as a young lawyer, to begin working for the NBA Players’ Association. Soon after, the North American Soccer League retained the firm to challenge the NFL’s cross-ownership restrictions, and Kessler was once again assigned to the case. “None of it was planned—it was just the way my early career developed, and I was just taking advantage of opportunities as things went forward.”
Kessler’s early work unfolded at a time when “sports law” was not even recognized as a field. “There was no sports law when I began,” Kessler said. “There were almost no cases, no classes in law school about sports law. No one would even think of such a thing or ask such a question.”
The Legacy of Free Agency
Among the pivotal changes Kessler has helped drive, the establishment of free agency stands out as a turning point in professional sports. For younger players and fans, it is almost impossible to imagine a world without it. “All they know their professional lives, and as fans, is free agency. They couldn’t imagine it didn’t exist, but it did not,” he said in a previous interview.
The battles to create that system were fierce, fueled by a narrative owners had pushed for decades. “The prevailing argument by the owners for 50, 60, 70 years was that if you allowed athletes the freedom to change teams it would destroy sports, fans would stop going to the games, there would be no competitive balance, and it would be the end of all sports as we know it,” Kessler explained. That message, he noted, was propaganda that many fans came to believe. Small-market supporters in particular were convinced that free agency would doom their teams. “And that was a total fabrication,” Kessler said. “The argument was ludicrous. Today anyone knows that free agency has been very good for sports and players.”
Standing Beside Athletes
Many of Kessler’s most important cases are remembered not only for their legal outcomes, but also for how they changed public perceptions of athletes. Representing Tom Brady in “Deflategate,” the U.S. Women’s National Team in their equal pay fight, and players across the NFL, NBA, and other leagues, Kessler has seen firsthand the courage it takes to challenge powerful institutions.
When asked how he balances the legal fight with the impact on a client’s identity and legacy, Kessler was quick to turn the spotlight on the athletes themselves. He explained that they are the ones willing to endure scrutiny and “take the heat” in order to push for change. As an example, he pointed to the U.S. Women’s National Team’s equal pay fight, where players risked their reputations and careers without knowing how the battle would end, yet chose to lead it anyway. To Kessler, their willingness to face those risks is nothing less than “a tribute to all these athletes” who refuse to back down from the fight for what they believe in.
Taking on the NCAA
Kessler has also been at the forefront of dismantling the NCAA’s longstanding model of amateurism. As he explained, “the NCAA worked very hard for decades to create the myth that college sports are all about the amateurism, and that there is some notability or purity in being an amateur athlete, and that’s what had to be protected, and that’s what their compensation restricti ons were doing. And that myth was widely believed.” For nearly forty years, the NCAA leaned on dicta from the Supreme Court’s 1984 Board of Regents decision, language praising amateurism even though the case was actually about television rights, and the Court did not revisit the issue until Alston in 2021.
In Alston v. NCAA, the Court unanimously struck down restrictions on education-related benefits. By then, Kessler observed, billion-dollar media contracts and multimillion-dollar coaching salaries had made the claim of amateurism impossible to square with reality. The most recent step came with the House v. NCAA settlement, which now permits Division I schools to provide up to $20.5 million annually in additional benefits and scholarships to athletes. “That’s really going to be transformative for a lot of college athletes,” Kessler said.
Still, not every conference has embraced the new model. While the Power Five conferences were required to join, the Ivy League and the Patriot League have not yet opted in. Kessler explained their reasoning by pointing back to the Ivies’ longstanding refusal to offer athletic scholarships, a position he called “a little hypocritical.” Although the Ivies insist they do not provide athletic scholarships, many athletes are admitted in part because of their athletic ability and then receive generous need-based aid that covers their costs. “So, in the same way they don’t give sports scholarships, they don’t want to make the payments to the athletes — that’s their rationale,” he said.
Ivy League athletes can still pursue third-party NIL deals, and Kessler suggested alumni support may become an avenue to offset the restrictions. But he cautioned that the Ivies’ stance could eventually create recruiting disadvantages. Many athletes value the academic prestige of an Ivy League education, yet if compensation is available at peer institutions, the decision calculus changes. “If you’re a really well-recruited basketball player at Harvard, maybe you go to Stanford instead,” Kessler explained. “There may be a big difference between a Harvard education and, you know, a lower ranked school education — but between Stanford, not so much. So, we’ll see how that works out.”
The Future of College Sports
Looking ahead, Kessler sees a host of unresolved issues that will define the future of college sports. One set of cases in Philadelphia is testing whether athletes should be treated as employees entitled to minimum wage, litigation that could fundamentally alter the structure of college athletics. Broader debates are also looming over whether athletes should be able to unionize and collectively bargain, though Kessler cautioned that this will not be resolved quickly. “That’s not going to get resolved anytime soon,” he said, pointing out that shifts at the National Labor Relations Board will largely determine the pace of change. He also noted that House v. NCAA is only the beginning of a new compensation era: how schools implement revenue-sharing, how benefits are distributed, and how third-party NIL opportunities are regulated will continue to spark battles. For Kessler, these questions mark the next frontier of athlete rights, and they could prove as transformative as the fights over free agency and amateurism in decades past.
Advice for Future Lawyers
With a career defined by landmark cases that reshaped both professional and college sports, Kessler has earned a reputation for knowing how to win the toughest battles. When asked what guidance he would give to students entering the field, his answer combined the fundamentals of good lawyering with the realities of breaking into sports law.
First and foremost, Kessler emphasized that success in any area of practice begins with mastering the basics. “The first thing I’d say is work really hard in law school to become the best lawyer you can be, because no matter what you do, your ability as a lawyer matters,” he advised.
For students interested in sports law specifically, Kessler urged openness to every possible pathway. “Cast your net wide,” he said, pointing out that opportunities can arise in unexpected corners of the industry, from leagues and teams to unions, agencies, or player associations. In his own career, many of his defining cases came not by design but by chance, and he encouraged students to approach the field the same way: by staying flexible and taking advantage of opportunities as they appear.
Finally, he turned to the question of making a lasting impact. For Kessler, that requires a willingness to step into uncertainty. “Don’t be afraid to take on hard cases, and don’t be afraid to try to create new legal principles if there are good grounds to do so,” he said. Playing it safe, in his view, may lead to steady work, but it won’t move the law forward. “If you just do cases where there’s no risk of failure, it’s not going to be much of an interesting practice, and you’re not going to make as much of an impact.”
Law student at the University at Buffalo.
Leave a Reply