Teammates On and Off the Field: Two CWSL Alumnae Leading the Charge in Sports Law

This is a feature also shared in the CWSL Spring 2025 Alumni Magazine. You can find a pdf of these pages here.  

There’s a lot to be said for being in the right place at the right time. But for Cassie McBride and Lauren Strackbine, two California Western School of Law alumnae who now serve as chief legal officers for professional sports teams, timing was only part of the story.  

Equally important? Knowing when to “shoot your shot.”

That phrase, said more than once during a conversation with Lauren, could just as easily describe the trajectory of both women’s careers. Today, Cassie is Chief Legal Officer for the NFL’s Tampa Bay Buccaneers, and Lauren recently became General Counsel for the NHL’s San Jose Sharks. These two women now share not only a close friendship but remarkably parallel journeys in the competitive, male-dominated world of sports law.

Cassie’s path began with a moment of boldness while still at California Western. She reached out via LinkedIn to a California Western alum working for an MLB team — and it worked. That message led to an opportunity which in turn helped launch her into roles with the  Los Angeles Angels and later the Jacksonville Jaguars. “It all came from a cold LinkedIn message,” she said.  It’s the kind of bold move she encourages others to make. Trust your instincts and take the leap.

Lauren and Cassie knew each other from law school — not best friends, but friendly enough to stay in touch. “We had both interviewed for similar internships along the way,” Lauren said. “And we kind of kept in touch just randomly after graduation.”

Years later, that casual connection would lead to an unexpected turning point at a law school colleague’s wedding. Cassie had just moved to the Jacksonville Jaguars. Lauren was still aiming for a role in sports. “She asked me, ‘What have you been up to? Like, are you still trying to get into sports?’” Lauren recalled. “And I said, yeah, that’s still the goal.”

There wasn’t an opening at the time, but Cassie mentioned that something could come up down the ine. “A few, I don’t know, three or four months, maybe later, she called me and was like, ‘Hey, we’re going 
to be looking for somebody,’” Lauren said. Cassie said the family that owned the Jaguars was building an amphitheater and undergoing a HIPAA audit, exactly the kind of work Lauren’s previous health care background had prepared her for. “That was how my medical and health care experience kind of landed me there.”

Small School, Big Impact

While their professional lives have taken them to opposite coasts now, both women still speak with real affection about their time at California Western. For Lauren, California Western’s intimate setting 
was a major draw. It gave her the chance to build real relationships with both peers and professors, something not always experienced in larger institutions. The school’s feeling of community helped her build the confidence and support network she’d later rely on, professionally and personally, including the early connection that would eventually circle back when Cassie brought her on board.

Cassie echoed similar sentiments about her time at  California Western. She talked about how the law school’s focus on practical training and community made a lasting impression. That sense of support and belonging helped her build the confidence to carve  her own path.

Changing the Game

It’s not lost on either of them that their rise comes in an industry historically dominated by men. “When I first started, there weren’t a lot of women in these roles,” Cassie said. “And now I look around and see more of us, not just in the room but leading the conversation.” Lauren agrees, adding, “Representation matters. It changes how decisions get made.”

However, they’re not content to be the exception. They want to be part of a broader movement to normalize women in leadership roles across sports, law, and beyond. Cassie put it simply: “We’ve come a long way. But there’s still work to do.”

Redefining Success

For both Lauren and Cassie, their definition of success has evolved over the years. Early on, it may have looked like landing the dream job, but these days it’s more about how they show up for the people around them. “Success is making sure the people you work with enjoy working with you back,” Lauren said. “That’s such a huge thing.” For her, leadership means being the kind of person others can turn to. “If you come to me, we’ll problem-solve. Knowing people trust me enough to do that, that’s success.” Cassie echoed that sentiment in her own way: it’s not about titles or trophies, it’s about being a steady, trusted presence in a world that’s always moving fast.

Full Circle

The story of Cassie McBride and Lauren Strackbine isn’t just about climbing the ranks or checking professional boxes. It’s about persistence, timing, friendship, and using your network and your voice to build the career you want.

They may not have been best friends in law school, but years later a chance conversation at a wedding cracked open a new chapter for them both. It wasn’t fate, it was preparation, persistence, and timing. Their story proves that careers aren’t linear. They’re built moment by moment, connection by connection, with just enough boldness to change everything.

And when two California Western grads happen to be the ones calling the shots from the front office of major sports franchises? Well, that’s a team we can all root for. Because if their story proves anything, it’s this: When the moment comes, don’t hesitate … shoot your shot.