Attorney 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.”

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 Law 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.”
 

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