Kaleisha Stuart was 14 and working at her first job, making $5.15 an hour at Chuck E. Cheese.
“My job was to dance in the scratchy Chuck suit, host children’s birthday parties, clean stinky bathrooms and stamp endless tiny wrists with numbers matching those of their parents,” Stuart said. “I vividly remember one evening noticing the setting sun as I wiped down tables. It was then that I decided to go to college and get a job where I could use my brain as opposed to being on my feet all day.”
Two decades later, Stuart is still in the world of entertainment, albeit in a vastly different position. She is the deputy general counsel of the Dallas Cowboys, the most valuable sports franchise in the world, where she has led complex commercial contractual agreements, joint ventures and partnerships, and negotiated extremely sensitive employment-related matters for one of the most high-profile businesses in the world.
Top Cowboys executives say Stuart has become a national leader in sports law and sports business.
Business Briefing
Stuart said her position now “is nearly unrecognizable from the one I took in 2016.”
“As the legal department for all the Jones family businesses, there are companies and projects I support now that didn’t exist when I started,” she said, pointing to the luxury gym Cowboys Fit, the high-end co-working space called Formation, the private social club Cowboys Club and tens of thousands of square feet of commercial real estate. In recent years, she has added matters related to employment law, intellectual property protection and commercial real estate to her portfolio.
Cowboys chief financial officer Tom Walker told The Texas Lawbook that Stuart has the “ability to see the positive in almost every situation” and looks for solutions that benefit all parties.
“Kaleisha addresses each situation with an eye towards the positive outcome, which often helps provide a sense of calm to the other folks she’s working with,” Walker said. “I’ve seen that in somewhat tense employee-relation matters as well as in time-sensitive contract issues. Her sense of calm actually helped keep the situation far more steady and on task.”
Despite being only 35, Stuart has achieved some extraordinary recent successes, including:
Negotiating sponsorship deals exceeding $25 million in the past two years;Helping bring nearly 50 high-profile public events to AT&T Stadium in Arlington and The Star in Frisco, including Taylor Swift, Metallica, Beyoncé, Ed Sheeran and Zach Bryan concerts, international soccer matches and WrestleMania;Playing a leading role in securing the landmark sponsorship agreement to keep Miller as the Official Beer of the Dallas Cowboys; and Demonstrating her commitment to advancing legal education in the industry by co-creating and co-teaching an advanced-level sports law class at SMU Law School and by helping to develop a curriculum for the American Bar Association’s annual ABA Forum on Sports and Entertainment.
“During her time with the Cowboys, Kaleisha has demonstrated a wide variety of legal skills that makes the business go,” said Cowboys General Counsel Jason Cohen. “She has run point on groundbreaking sponsorship and marketing agreements as well as helping to close transformational real estate deals.”
Dallas Cowboys deputy general counsel Kaleisha Stuart at the team’s practice facility in Frisco, Texas.
Patrick Kleineberg/The Texas Law
Stuart said that her roots are integral to her professional successes. Her grandmother cleaned homes and her grandfather worked in the Kentucky coal mines. Her father served in the Army in Desert Storm and then worked for Union Pacific Railroad as a conductor and later a locomotive engineer. Her mother became an award-winning middle school math and science teacher.
She was born in Germany during her father’s deployment and then settled in San Antonio, where Stuart spent most of her childhood.
“My upbringing taught me the value of a dollar, that nothing comes without hard work and that it is family that means the most,” she said. “I am proud of my humble beginnings because they have made me resilient. That I get to live this life, to do this job, for this brand is a miracle made possible only by the sacrifice and love of my hardworking family.”
When Stuart joined the Cowboys in 2016, she was the only Black woman lawyer working in-house for any NFL team. During her decade with the NFL franchise, Stuart has fostered a more inclusive and supportive workplace through the creation and launch of The Fellowship, a Black employee resource group that hosts the annual Black History Month luncheon, and the creation of the Cowboys’ annual Juneteenth festival, which supports local Black-owned businesses, features musicians and other artists and is sponsored by Miller Lite.
“Kaleisha creates an environment that we can all listen and learn from each other — fostering an open dialogue and a thoughtful approach,” Cohen told The Lawbook.
The Association of Corporate Counsel’s DFW Chapter awarded Stuart with its prestigious 2024 DFW Corporate Counsel Award for Achievement in Diversity and Inclusion.
“Kaleisha’s tenure has been marked by unparalleled achievements, from spearheading groundbreaking sponsorship deals to negotiating multimillion-dollar contracts,” said McCathern Law partner Stephanie Almeter. “Beyond her legal accomplishments, she stands as a beacon of community support, fostering inclusivity through initiatives and mentorship programs. Her impact on the sports law industry and her commitment to empowering others make her an exceptional candidate for this prestigious recognition. Her proactive approach in reshaping the Dallas Cowboys’ music management strategies in response to industry shifts underscores her adaptability and foresight.”
Stuart’s success, according to Jeff Becker at Haynes Boone, can be seen in the way that she “demonstrates a keen understanding of the balance between legal precision and practical business needs.”
“Keeping Mr. Jones happy for almost a decade is strong evidence that Kaleisha’s time with the Cowboys has been a constant series of professional successes,” Becker said.
The Texas Lawbook is an online news publication focused on business law in Texas. For a longer version of this story, visit texaslawbook.net.
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