Tiffany M. Cunningham, Esq.
Tiffany M. Cunningham, Esq., is a Global Sports & General Entertainment Media executive who has spent over 20 years navigating the high-stakes world of media rights and corporate strategy. Following a successful 16-year career at The Walt Disney Company, she now leads her firm’s Sports Media practice in addition to servicing general entertainment clients.
A trusted strategic advisor to C-suite executives, leagues, tech innovators, top-tier content creators, athletes, and talent, Tiffany has safeguarded some of the world’s most valuable intellectual property. Her expansive portfolio of expertise includes guiding game-changing deals for iconic entertainment and sports brands like ESPN, Disney, ABC, FOX, Lucasfilm, Marvel, and The Tennis Channel.
Tiffany is a master negotiator and a recognized authority in global media rights. She has architected landmark licensing deals across the digital landscape, partnering with global streamers and retail giants to redefine how audiences consume content. Beyond traditional media, she is a forward-thinking stakeholder in the future of entertainment, advising on cutting-edge initiatives ranging from ecommerce and direct-to-consumer platforms to AI-driven sports tech and live-streaming apps.
Throughout her career, Tiffany has been at the helm of some of the most monumental shifts in modern entertainment. She helped launch the premier direct-to-consumer platform Disney+, led critical post-acquisition legal strategies following the historic Disney/Twentieth Century Fox merger, and plays a pivotal role in the digital transformation from traditional cable to the streaming era. Armed with deep institutional knowledge and a passion for the business of sports and entertainment, Tiffany continues to break barriers and engineer innovative solutions that shape the future of media.
• Licensed Attorney
• USC Gould School of Law – Juris Doctor (J.D.)
• University of Southern California – Bachelor’s Degree
• Sports Lawyers Association
• Profluence Sports
• Women in Sports & Events
• Board member candidate for nonprofit focused on foster youth transitioning out of the system
• Mentoring youth
• Sports Lawyers Association committee member
What do you attribute your success to?
I attribute my success to God & grit. I have a very blessed life, and it's not one that's not had its trials, but it's had trials and triumphs, and I attribute that to him.
What’s the best career advice you’ve ever received?
Always ask for what you want. The worst case scenario is they say, "no," and you're in the same position you were before asking. But they could always say, "yes."
What advice would you give to young women entering your industry?
I think it's grit, but what is a predicate for that is knowing what your purpose is. I care very much about the youth. I look at young people today, and I see so many of them, sadly, walking around aimlessly, not knowing what their purpose is. I really do believe we were all uniquely created to make a contribution here that no one else can make. We have a choice to make it or not, but I do believe that we each have a unique gifting. I'd advise young women to identify their purpose first. Once you're able to pinpoint it, you'll find that all of the desires you have, the things that make you excited, the things that fulfill you, will be aligned. The grit part then becomes easy, because you're chasing the thing that you love, that energizes you, and excites you.
What are the biggest challenges or opportunities in your field right now?
There's been significant disruption in my field--i.e., content distribution. Most people used to have cable bundles--they were paying Comcast or Charter--which they got sick of, because the bills were so exorbitant. Then they go to these streamers, and they think they're getting a discount, but when you add up all your subscriptions, you're not. There's a strategy in all of that. I have done deals where the consumer clicks 'I agree' for a free trials. It was only supposed to be a 7-day free trial, but many people forget about it.
What values are most important to you in your work and personal life?
-Faith
-Authenticity over politics
-Pragmatism/ solutions-oriented thinking
-Trustworthiness/ Integrity
-Conscientious advocacy
-Effectiveness (efforts actually achieve objectives)
-Relationships over self-serving networks
-Mentorship