Unrivaled 2025: Jeffrey Kessler of Winston & Strawn

You led a team that negotiated a historic settlement with the NCAA, settling three antitrust class actions that you brought: Hubbard v. NCAA; House v. NCAA; and Carter v. NCAA. The deal is set to distribute nearly $2.8 billion to current and former college athletes, generate $20 billion in new payments and benefits to Division I college athletes over the next decade, and preserve the current Name Image and Likeness (NIL) system of third-party payments for athletes. (A federal judge approved the settlement in early June.) Can you tell us about your trial strategy?

I was co-lead class counsel, with Hagen Berman’s Steve Berman, in a more than decade-long effort to bring economic justice to Division 1 college athletes. The journey first required a trip to the Supreme Court in Alston v. NCAA, in which our class action trial verdict striking down the NCAA restraints on education-related benefits was affirmed by the Supreme Court in a 9-0 ruling.

We then followed with the House litigation, which brought an antitrust class action against the NCAA’s restraints on compensation for the D-1 athletes’ Name, Image, and Likeness rights. House was scheduled for a jury trial in which the NCAA faced trebled damages totaling more than US $12 billion.

We next followed with the Hubbard litigation, which added hundreds of millions more in trebled damages for denying D-1 athletes the education related benefits held lawful in Alston. Then, we followed with the Carter litigation, which asserted an antitrust class action against the remaining NCAA compensation restraints.

The combined threat of these litigations enabled us to achieve the landmark settlement providing almost US $2.8 billion in damages and a new revenue sharing system in which athletes are expected to receive more than US $20 billion in life-changing payments over the next ten years.

Can you describe a major hurdle that happened during the course of this trial? How did you overcome it?
The landmark class action settlement we negotiated required court approval. While more than 100,000 class members showed their support for the agreement, a small number expressed concerns. After a day-long hearing, the court overruled almost all of the objections but withheld approval and sent the parties back to see if an agreement could be reached to provide grandfathered protection to those athletes being cut from teams as a result of new roster limits. We then engaged in pressure-filled negotiations with the NCAA in which the additional protections that the court requested were put in place.

When did you first know you wanted to be a trial lawyer? What clicked for you?
I fell in love with being a trial lawyer during the three-month jury trial in McNeil v. NFL. In that case, we won an antirust verdict for NFL players that led to the creation of free agency. It was my first chance to cross-examine key witnesses under intense public scrutiny, and I will never forget the rush of securing the answers I needed from the NFL’s expert and drawing supportive gasps from the jurors. Then, there was the tense rush back to court for the jury verdict, the thrill of learning that we won, and the jubilation that followed.

What are the major keys to winning over a jury or a judge?
The key to persuading a jury or a judge is to communicate a clear and compelling story that explains why your clients should win. Complicated facts and legal arguments have to be simplified, and fact finders have to understand why the law and the equities compel a ruling in your client’s favor. Developing a sense of trust is also essential.

What is the best advice you give young trial lawyers?
“The best advice for a young trial lawyer is to find your personal style, never do anything to undermine your credibility, prepare thoroughly, and craft a strong narrative to explain why your client should win.”