This week on The Intersection, Jeffrey Kessler, one of the world’s leading sports attorneys and co-executive chairman of Winston & Strawn, joins Mike Sitrick and Sallie Hofmeister to discuss the power of PR strategy in litigation, and the impact of media influence on legal outcomes. He shares his firsthand experience with high-stakes cases, including the NCAA v. Alston case and major NFL disputes—revealing how media coverage helped shape their direction.

Kessler will lay out the details of his landmark Supreme Court win in NCAA v. Alston, which reshaped college athlete compensation and led to the historic NIL (Name, Image, and Likeness) settlement. He also reflects on representing the U.S. Women’s National Soccer Team in their equal pay lawsuit, explaining how a carefully orchestrated media strategy turned public sentiment into legal leverage.

“As lawyers, we sometimes have to take hard cases that are controversial. Not everybody's going to love you for it. You may be attacked for it. But it's part of what our profession requires.” – Jeffrey Kessler

From representing Tom Brady in Deflate-Gate and leading the lawsuit that resulted in the 2011 NFL lockout to fighting for college athletes’ compensation rights and defending Ray Rice after his career-ending suspension, Kessler has handled some of the most controversial sports cases of our time. But beyond the courtroom, he’s seen firsthand how legal media strategies shape public narratives—and why controlling the story is just as important as winning the case. 

As co-chair of Winston & Strawn's global Antitrust/Competition Practice and the former co-chair of its Sports Law Practice, Kessler has worked with such corporations as Panasonic and Activision Blizzard, as well as the Player Associations for the NBA, NFL, and MLB.

This episode explores some of the biggest legal cases in sports, as well as media influence on legal outcomes, PR strategy, crisis management in PR and sports, litigation in professional athletics, and public opinion.

About Sitrick and Company

Sitrick and Company is a Los Angeles-based public relations firm founded by Michael Sitrick specializing in corporate, financial, and crisis communications. Known for its expertise in high-stakes situations, the firm has handled reputation management, litigation support, and media strategy for high-profile clients. It operates offices in New York City and Washington, DC, and is recognized as a leader in strategic communications and crisis management

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