Wayne Law alumnus marries love of sports with legal work

For any attorney who loves sports, Jason Hillman has the ultimate dream job.

The 2001 Wayne State University Law School graduate is basketball chief of staff and general counsel for the NBA's Cleveland Cavaliers and for Cleveland's Quicken Loans Arena. The team and the arena are owned by well-known entrepreneur Dan Gilbert, Wayne Law class of 1987.

Hillman began working for the Cavs as company counsel in 2005, and was promoted over and over until he earned his current job in 2017. From 2001-05, he was an attorney in the Real Estate Transactions Group at Jaffe Raitt Heuer & Weiss PC in Southfield. His bachelor's degree from Michigan State University is in journalism. Before law school, Hillman worked as a sportscaster on TV and radio in the Detroit area.

And for a while, when he worked in Cleveland, he did some sideline work as intermission host and rink-side reporter for some broadcasts of Gilbert's American Hockey League franchise, the Cleveland Monsters.

"With the demands of the full-time basketball schedule now, those days are in the rear-view mirror, but remain outstanding memories," Hillman said. "I miss it. There is nothing quite like the thrill of live television or radio."

7 questions
with Jason Hillman

His job now offers a great deal of variety and plenty of chances to think fast on his feet every single day. Hillman loves it.

"I am responsible, as part of a great team, for managing our staff of 45 people plus our players," he said. "The job is incredibly demanding because I am charged with knowing our collective bargaining agreement and associated rules and governing documents, and how we operate on a daily basis in compliance with them. With a set of responsibilities ranging from core legal to more specific basketball principles, there is a wide range on my plate, and I pride myself on being like a Swiss Army Knife in terms of versatility."

In 2016, he was part of the team of people who ultimately scored the Republican Convention for Cleveland, and a few weeks before that event, the Cavs won the NBA championship. Heady times for Hillman.

"With Quicken Loans Arena serving as the convention hall, there were several governing agreements to draft, negotiate and administer in conjunction with the host committee, and RNC," he said. "We had incredible weather, a safe and peaceful convention week and an opportunity to show the world what Cleveland was all about."

Like him, his wife and three daughters have come to love the city of Cleveland.

"They know what I know: It is a unique privilege to be a part of (Gilbert's) organization and the NBA and to live in this city," Hillman said.

His legal education at Wayne was "an incredibly important and invaluable experience for me and my fellow classmates," and ultimately is what allowed him to marry his sports background with his work.

Hillman stays in touch to this day with some of his law school professors, including Professor Peter Henning, Distinguished Professor Alan Schenk, retired Professor Lawrence Mann, and Associate Professor Emerita Janet Findlater.

"The faculty at Wayne Law remains second to none, and I've been incredibly fortunate to remain in touch with so many of them who influenced us all," Hillman said. "Our class enjoyed being with each other and managing the demands of law school together in a collaborative way. Wayne Law prepared me to juggle the demands of a high-pressure environment, while emphasizing human relationships, all while establishing a first-rate academic legal education. I could not imagine a better place to go to law school."


Seven questions with Jason Hillman

Q: Will you describe your work as general counsel for an NBA team?

A: The general counsel position for a sports organization, probably not unlike the general counsel position elsewhere, to me is similar to being a primary care physician. You may deal with 10 different matters in a particular day, ranging from employment to intellectual property to lease compliance to managing a credit facility - and everything in between. In some areas, you develop subject matter expertise, and in others, you rely on outside counsel. In that sense, I draw the comparison to the primary care physician who must be able to diagnose everything that he or she sees from patients in a given day before referring to a specialist, if need be.

Q: What are some of your outstanding memories about your time at Wayne Law?

A: Our class was incredibly close. We took school seriously, but as a group did not feel like we had to compete against one another, and that, as I understand, is a rarity in some other law school environments. One of the finest memories I have was taking the Michigan bar exam in East Lansing (Go Green!) and celebrating with our classmates that night.

Q: What was your first job?

A: My first real job was washing dishes and clearing the counter at Hunter House Hamburgers in Birmingham. I loved that job, but I ate way too many burgers in the summer of 1988.

Q: Who are some of your role models?

A: On the legal side, Rick Zussman at Jaffe, where I was fortunate to work for four years out of school. His work ethic, attention to detail and professionalism are second to none. Frankly, all my colleagues at Jaffe were incredible mentors and friends, and remain so to this day. In the basketball world, I remain in awe of Adam Silver, our NBA commissioner, and his leadership of our league. He is passionate about growing our game, and doing so while helping establish our league as a model of social consciousness.

Q: What are your favorite leisure-time activities?

A: I still play baseball to this day in an adult league. If I'm not with my family, you'll find me on a baseball diamond. Also, I'm a Broadway junkie. We are fortunate on Cleveland to have a robust theater community, and it's a great way to turn my phone off for a few hours and enjoy the theater.

Q: Describe yourself growing up and how you were as a kid?

A: I loved sports, especially baseball, and I was always outside looking for some type of game. I grew up in a great community in Huntington Woods, where my mom still lives. I was incredibly fortunate to go to high school at Detroit Country Day, which prepared me for college and law school. I spent summers as a kid at Camp Tamakwa in northern Ontario, where our daughters also go today. If I was not playing or watching sports, it was piano and Broadway shows.

Q: What's the best part of your job?

A: Ever since Little League baseball in Huntington Woods, I've been a competitor. I cherish every day being a part of our basketball group, and was beyond fortunate to make our finals run in 2017-18 with, in my opinion, one of the best players, if not the best, in the history of the game. To do so in a city like Cleveland, which is similar in so many respects to Detroit, where there is a hard-charging work ethic and incredible hometown pride, is a gift.


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