His takeover of the Tribune Co., a group of Los Angeles Times employees argued in a lawsuit filed in September, was a deal "designed to benefit corporate insiders at the employees' expense."
In a statement after the suit was filed, Zell dismissed the employees' claims as "frivolous" and "unfounded."
The infamy brought on by 2007 Tribune deal followed what had been more than four decades of deal-making glory in the real estate business, starting in his college days. His business savvy dates back even further.
Zell's parents were Polish-Jewish immigrants who fled their home country on the eve of the 1939 Nazi invasion. They settled in Chicago, where Zell was born in 1941.
"My father made a life-and-death decision at age 34, and he was right," Zell told Dividend, a University of Michigan business school alumni magazine, in 2006. "My dad was very, very strong and very confident. I had to be very confident and strong to succeed in his shadow."
His first taste of business success came at age 12 from an unlikely source: Playboy magazines. After discovering a newsstand that sold the adult magazines, Zell began buying them and reselling them to classmates for $3 -- six times more than he'd originally paid for each, according to Dividend.
By the time Zell entered college at the University of Michigan in Ann Arbor, he had turned his sights to real estate and took jobs managing different apartment buildings while still in school.
Eventually, he would join real estate developer Don Chisholm in buying properties in the college town.
Chisholm remembered how Zell once convinced a reluctant seller, a woman who lived with her brother. She worried that her brother wouldn't be able to find his way to their new home after a night of drinking if they moved.
Zell made her a deal: If she sold, Zell would find her a new house close to a bar and would install a ramp and a handrail just for her brother. It worked.
"He was so smart and had so much drive," Chisholm told ABCNews.com. "The perseverance and the attention to detail was remarkable at that point -- he was just 21 or 22."