At age 14, Kaleisha Stuart was working at her first job, making $5.15 an hour at Chuck E. Cheese, which she describes as “one the most influential experiences of my youth.”
Her job was to “dance in the scratchy Chuck suit, to host children’s birthday parties, to clean stinky bathrooms and to stamp endless tiny wrists with numbers matching those of their parents,” she said. “I vividly remember one evening noticing the setting sun as I wiped down tables. It was then, as I stood in the sensible SAS shoes my mother lent me, that I decided I wanted to go to college and get a job where I could use my brain as opposed to being on my feet all day.”
“Growing up, I was taught what my father dubbed the ‘18-90 Rule’ — once we turned 18, we had 90 days to choose boots or books,” Stuart told The Texas Lawbook. “My older brothers, following in our parents’ footsteps, chose boots, though later got degrees through their military service. I opted for books.”
Two decades later, Stuart is still in the world of entertainment but in a vastly different position. She is the deputy general counsel of the Dallas Cowboys, the most valuable sports franchise in the world.
Despite being only 34, Stuart has achieved some extraordinary 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.
When Stuart joined the Cowboys in February 2016, she was the only Black woman lawyer working in-house for any of the NFL teams.
Since then, Stuart has demonstrated her commitment to fostering 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.
“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. “Handling employment matters to IP to real estate with a deft touch. She has run point on groundbreaking sponsorship and marketing agreements as well as helping to close transformational real estate deals.”
“In terms of D&I, she is natural,” Cohen said. “She creates an environment that we can all listen and learn from each other — fostering an open dialogue and a thoughtful approach.”
“People should know that Kaleisha cares — she cares about herself, others, the world around us and the Dallas Cowboys,” she said.
The Association of Corporate Counsel’s DFW Chapter and The Texas Lawbook award the 2024 DFW Corporate Counsel Award for Achievement in Diversity and Inclusion to Kaleisha Stuart.
ACC DFW and The Lawbook will honor the 2024 finalists and announce the winners at the DFW Corporate Counsel Awards ceremony this Thursday at the George W. Bush Institute.
“Kaleisha, a dynamic force in her ninth season with the Dallas Cowboys, epitomizes a remarkable journey,” said McCathern Law partner Stephanie Almeter, who nominated Stuart for the award. “Originating from humble beginnings as the daughter of a schoolteacher and railroad worker, her commitment to hard work and service resonates profoundly.”
“Kaleisha’s tenure has been marked by unparalleled achievements, from spearheading groundbreaking sponsorship deals to negotiating multimillion-dollar contracts,” Almeter said. “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.”
Premium Subscriber Q&A: Kaleisha Stuart discusses the traits she seeks in outside counsel, what outside counsel need to know when working with her and more.
Almeter said that Stuart’s contributions go well beyond her obvious legal talents and expertise.
“Initiating a quarterly virtual gathering for Black women lawyers in NFL teams, she cultivated a platform fostering solidarity and mentorship across career stages, evolving it into an annual in-person summit scheduled for 2024,” Almeter said. “Additionally, her counsel in establishing the Dallas-Fort Worth chapter of WISE (Women in Sports and Events) showcased her commitment, crafting governance documents and form contracts for the organization.”
In an interview with The Lawbook, Stuart points out that she was the only Black lawyer working in-house for an NFL team in 2016.
“Over the years, legal departments have grown and diversified,” she said. “Noticing this trend, I decided to create a group for the Black women lawyers working at NFL teams. The goals of the group were simple — to make Black women taking on these new roles feel immediately welcome, to have a safe, supportive outlet to share ideas or ask questions and, ideally, and to make new friends. It is a wonderfully supportive group, and we certainly have made what I know will be some lifelong friendships.”
Stuart is a member of the board of directors for the AT LAST! Compassion Fund, where she evaluates applications, granting crucial financial aid to underprivileged families in Dallas. She has also served as a career coach for the Sponsors for Education Corporate Law program, where she has provided mentorship and guidance to students throughout their summer internships.
“Within the Dallas Cowboys organization, Kaleisha has been instrumental in leading diversity, equity and inclusion initiatives,” Almeter said. “Her efforts in establishing the Black employee resource group and the creation of the annual Juneteenth festival reflect her commitment to fostering a more inclusive and supportive workplace.”
Stuart said that general counsel and in-house corporate legal departments “play an important role in improving diversity and inclusion in the legal profession.”
“As the conscience of the company, the legal department must model and implement values of diversity and inclusion within its own ranks if it expects the company at large to do so,” Stuart said. “I am fortunate to work in a department, led by Jason Cohen, that strongly values the role of women in leadership. Our department boasts six women, three women of color and two naturalized citizens. I love the quote ‘We don’t see with our eyes, we see with our whole lives,’ and together we bring a diverse and wide set of life experiences to solve the Cowboys’ legal problems.”
“In-house counsel and GCs also have the awesome ability to make incremental improvements to our profession by using its outside counsel spend wisely,” she said. “Whenever possible, giving business to qualified attorneys that share the company’s values creates a virtuous circle that rewards the law firms that support and treat their attorneys well.”
Prominent corporate lawyers say that the Cowboys’ senior executives deserve tremendous praise for continuing to support Stuart’s proactive work related to D&I.
“Kaleisha is absolutely unwavering in her commitment to diversity and inclusion efforts and gives freely of her time and knowledge, teaching, training and mentoring others,” said Haynes Boone partner Jeff Becker. “Within the Dallas Cowboys organization, she has been instrumental in establishing the Black employee resource group and creating the annual Juneteenth festival to support local black-owned businesses. Kaleisha has also been active in spearheading DEI efforts in the broader NFL and sports communities.”
Becker praised Stuart for her successful efforts to create a quarterly virtual gathering of Black women lawyers at NFL teams and for helping to establish the DFW chapter of WISE, which has the mission of empowering women in the business of sports with the tools to reach their career goals.
“As a diverse woman in the male-dominated fields of sports and law, Kaleisha’s leadership, mentorship and sponsorship of others is helping to break barriers and further diversify both industries,” Becker said.
Dallas Cowboys CFO Tom Walker told The Lawbook that Stuart “is one of the most important drivers of our largest employee resource groups — The Fellowship.”
The Cowboys’ Fellowship has three missions, according to Walker: support and develop Black employees at the Dallas Cowboys, engage all Dallas Cowboys employees in educational and cultural experiences and use the Dallas Cowboys platform to advance the cause of social justice through advocacy and community service.
“I can’t think of anyone more deserving of recognition for the DFW Corporate Counsel Award for Achievement in Diversity and Inclusion than Kaleisha,” Walker said. “Kaleisha’s leadership ‘off the field’ in our internal DEI initiatives has been instrumental since early in her career here, which is matched only by her success ‘on the field’ in helping guide our legal department through a period of unprecedented business growth. If you get five minutes to spend with her, you’ll understand why I feel as strongly about her recognition as I do.”
‘To Them, I Owe Everything’
Stuart agrees that her roots are integral to her professional successes.
She was born in Germany to two Americans who met and fell in love during their Army deployment. Her father served in the Army in Desert Storm and then worked for Union Pacific Railroad, first as a conductor and then worked his way up to become a locomotive engineer. Her mother juggled caring for her growing family and taking college classes. The family settled in San Antonio, where Stuart spent most of her childhood.
“Mom became an award-winning middle school math and science teacher — my very own Ms. Frizzle,” she said, referring to the teacher from The Magic School Bus. “My parents worked extremely hard to support our large family of five kids. My upbringing taught me the value of a dollar, that nothing comes without hard work and that it is family that means the most. It is this commitment to hard work and supporting my family that is my sole inheritance and what continues to motivate me today.”
“I am proud of my humble beginnings because they have made me resilient — and I come from a long line of resilience,” she said. “My dad sacrificed his physical health and risked his safety working on the railroad for 30 years. My mother spent three decades nurturing and educating our city’s poorest kids. They did it all so we could survive and so that us kids could maybe even thrive. 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.”
“It is to them that I owe everything,” she said.
Stuart’s paternal grandmother cleaned homes, and her grandfather worked in the Kentucky coal mines, “where early mornings and long shifts meant he and his fellow workers often only saw the sun on Sundays,” she said.
Stuart started at Texas A&M University majoring in economics and politics during the final, contentious months of the 2008 presidential campaign.
“That fall, I read Barack Obama’s beautiful memoir Dreams from My Father in an effort to better understand the man who would soon become our nation’s first Black president,” she said. “His story taught me that lawyers play an important role in shaping our society’s systems of power, and I felt incredibly drawn to be part of that legacy.”
She was elected president of the university’s pre-law society.
“Before I knew it, I was shipping myself off to California to learn how to ‘think like a lawyer’ at Stanford,” she said. “I am so lucky to have read that book and to have set on this path, because I love being a lawyer.”
After summer clerkships at Jones Day in Dallas and sportswear giant Nike, Stuart earned her law degree from Stanford in 2015.
Stuart said her summer clerkship with Jones Day played a significant role in her interest in sports law when she met capital markets attorneys David Kern and Jim O’Bannon.
“David and Jim took a shine to me,” she said. “I suspect it was because they saw that what I lacked in experience, I made up for with a hunger to succeed. That hunger was borne from the deep sense that I did not have a financial safety net to rely on if I failed, a keen desire to not be dismissed as the ‘diversity hire’ and a strong dedication to become great at my job. I worked incredibly hard for them, and in turn they dedicated their valuable, limited time to teach me.”
Stuart said she learned from Kern, O’Bannon and Hilda Galvan, who was the managing partner of the Jones Day Dallas office, what it meant to “truly understand their clients’ businesses.”
“This piqued my interest to learn more about what it might be like to work in-house, to truly align with your client’s business,” she said. “From there, I figured that if I were to work in-house, it would be important that the company I selected put something out into the world that I believed in and that mattered to its customers.”
‘Internship Changed My Whole Life’
With that in mind, Stuart sought and landed an internship with Nike’s legal department.
“I didn’t know it then, but that internship would change my whole life and set me on my path as a sports lawyer,” she said.
Stuart spent one year as an associate with Jones Day in 2015 and 2016 when a moment of “luck and preparation” hit.
A few of Stuart’s former colleagues at Nike were in town for a Cowboys game and meeting with Cowboys GC Cohen, and the Nike lawyers invited Stuart to join them.
“Jason mentioned to my old Nike boss that, as they were gearing up to move from Valley Ranch to the new practice facility and headquarters in Frisco, he was thinking about bringing on a young attorney,” Stuart said. “My old boss quipped that Jason ‘should just hire Kaleisha.’ I was in the back of the suite having a cocktail with Jason’s amazing wife — truly the best half — Karen and was not even aware that conversation had taken place.”
“In hindsight, this experience reinforced how key it is to take full advantage of any opportunity that comes your way,” she said. “If I hadn’t worked my tail off at Nike, my old boss would not have recommended me to Jason. But it’s not just hard work, I was extremely lucky to have been working in Dallas, as opposed to one of Jones Day’s other 40 offices, when the Nike crew came to town.”
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.
Stuart is also Cohen’s chief deputy, which means putting together and managing the legal budget, setting department goals and strategies and assigning work to the team.
“The most important and rewarding aspect of my expanded role is managing our paralegals and our newest lawyer,” she said. “So much of our work satisfaction is impacted by the quality of our supervisor, and I take the responsibility very seriously.”
Cowboys CFO Walker told The Lawbook that Stuart’s “admirable traits is her ability to see the positive in almost every situation.”
“Not that she has a naïve attitude toward the situation — rather that she 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.”
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. “Recently, I had the opportunity to see her in action, navigating a complex legal challenge with precision and creativity. Faced with a critical situation during a contract negotiation, Kaleisha was tasked with evaluating the legal risks of refusing to agree with the other side’s demands — a matter with potentially substantial business implications.”
“In this high-pressure and very time-sensitive situation, Kaleisha’s analytical skills and resourcefulness were on full display,” he said. “She identified and reviewed other relevant agreements already in place, which had difficult to interpret provisions. Kaleisha’s careful analysis revealed that the company already possessed the legal rights it needed, enabling them to refuse the other side’s last-minute demands. Kaleisha’s ability to think strategically, act decisively and provide a clear path forward was instrumental in securing a successful outcome.”
Foley partner Carrie Hoffman said Stuart’s strength as a lawyer is that “she is able to see the forest for the trees without effort.”
“Kaleisha has worked hard for her achievements but has not forgotten her path to get there, which enables her to recognize those efforts in others and work with them to help them reach their goals,” Hoffman said. “She has a true love of sports and has turned that passion into an interesting and fun career, which is something that is inspiring to young attorneys looking for their path.”
FUN FACTS: Kaleisha Stuart
- Favorite book: All About Love by Bell Hooks — a beautiful exploration of the topic and helped form my own general understanding of love and its role in guiding our lives.
- Favorite music group: Whitney Houston. Her 1987 song “I Wanna Dance with Somebody” to be a perfect tune – it makes you want to sing, dance and be happy.
- Favorite movie: I prefer a comedy special to a movie and can recite nearly every line of my favorite, Dave Chappelle’s “Killing Them Softly”, but if I am tuning into a movie, it is probably starring Diane Keaton, Jack Nicholson or, preferably, both.
- Favorite restaurant: Lemon Ricotta Gnudi at The Charles, followed by a tequila-based cocktail at Bar Charles, their lovely little hidden champagne lounge behind the kitchen.
- Favorite beverage: Coffee and I have a long and robust relationship.
- Favorite vacation: It’s simply impossible to pick just one because travel is one of my great joys in life. The top three probably include spending the most beautiful week of my life in Bora Bora, hiking around Arizona for three weeks with my parents and dog and exploring slave castles by day and beach parties by night as 19-year-old in Ghana.
- Hero in life: Professionally, it is my boss and mentor, Jason Cohen. He saw my potential as a baby lawyer, gave me the opportunity of a lifetime to work at the Cowboys and has taught me almost everything I know about being a lawyer in professional sports. Spiritually, Pema Chödrön, whose writings helped me understand how to navigate life, build compassion and endure pain. And personally, my parents, to whom I owe everything.