A NEW SERIES FROM THE EDITORS OF FORTUNE AND Sports Illustrated
THE FIRST TIME Junior Bridgeman, then the Milwaukee Bucks' super sixth man, learned how the smart money thinks, he was having breakfast at a Hyatt hotel in Oakland in the early 1980s with then-Bucks owner Jim Fitzgerald. As Bridgeman grabbed the local paper and scanned the sports section, Fitzgerald picked up The Wall Street Journal and pored over the stock tables. "Wouldn't it be great if we had a copy of next year's Journal today?" Fitzgerald said. "The money we could make!"
Bridgeman laughed, more out of instinct than anything else. That same day he revealed to Fitzgerald his desire to "get involved in something in the business world" when his NBA playing career was over.
That world, Fitzgerald told him, "only [has] two problems: people and money."
Bridgeman didn't get that joke either. He didn't grow up around Fitzgerald's type of humor—or money. In his hometown of East Chicago, Ind., his father, Ulysses, was a second-generation steelworker determined to ensure his descendants didn't follow in the family business.
Early on, an academic scholarship seemed to be the only hope his second-born child, whose real name was also Ulysses but who was known as Junior, had of avoiding a career covered in soot. But as a senior Junior starred on a Washington High to the 1971 Indiana state championship, and Louisville offered him a basketball scholarship.
In 1975, after helping the Cardinals reach that year's Final Four and completing his degree in psychology, Bridgeman took the LSAT, such was his lack of confidence in his ability to make the NBA. He can't remember what he scored on the test. Why would he, after Los Angeles took him with the eighth pick of the draft?
A week later the Lakers shipped Bridgeman to Milwaukee in a trade that landed them Kareem Abdul-Jabbar. During 10 seasons in which he made a franchise-record 711 appearances, Bridgeman averaged 13.9 points while making just 105 starts.
Bridgeman was one of the league's best sixth men, and he was equally adept in his role as president of the players' association. It was in collective-bargaining meetings that Bridgeman became curious about the business world—specifically during recesses, when heated debates about player salaries would yield to casual talk among the owners about movie and real estate deals.
"It became obvious to me that these other things they were doing were more important than owning a team," Bridgeman says. The years he spent haggling with owners were better than a stint in business school. Cheaper too. "They were two or three questions ahead," Bridgeman says. "It was an unbelievable education."
Bridgeman, whose highest NBA salary was $350,000, retired in 1987 at age 33. He had spent off-seasons working at an insurance firm and at the front desk of a Howard Johnson, but in April 1988, seizing on his love of hamburgers, he bought five Milwaukee-area Wendy's franchises. Even though he had the seed money to do so, it was a challenge to persuade investors that he had the savvy as well. Not even a banker with whom he had done business for more than a decade would take Bridgeman seriously during a meeting with him and his business partner, Paul Thompson. "Every question that she asked was directed to Paul," Bridgeman says. "She didn't view me as anybody other than, 'You played basketball, you made some money, you bought these stores; he's running 'em.' That's when I learned that when it came to business, people were going to see me one way."
Bridgeman worked tirelessly to change that perception, doing everything from flipping burgers to working the counter. His best store in those early years grossed $800,000 annually, roughly what the average Wendy's did at that time. "Failure," he says, "was not an option."
The path to success began by drawing on his experience as a team-first player. Bridgeman rejected the belief that Wendy's burgers were good enough to sell themselves. People, it turned out, were much more effective. So Bridgeman hired better employees and began investing in them as people, helping some make rent and bailing others out of jail. Once they saw how much he cared about them, they worked harder for him.
He also started talking like a basketball coach. "What I tried to do was to get everybody to understand that we were a team," he says. "We work together as a team, we win as a team and we lose as a team."
Today those five original Wendy's restaurants, which reap more than $1.5 million apiece in annual sales, are the cornerstone of Bridgeman's 240-store portfolio—making him the second-largest franchise owner in the country. Bridgeman also owns 125 Chili's restaurants and scads of other retail franchises, most of them clustered in the upper Midwest. Eighteen thousand people crowd his employee roster. His net worth is at least $200 million.
Bridgeman, who briefly owned a minority stake in the Sacramento Kings, is an eager mentor to NBA players who express an interest in putting some skin in a totally new game. Just last year he teamed up with Pistons guard Chauncey Billups to buy 30 more Wendy's restaurants in the St. Louis area.
Still, for every player like Billups, there are one or two who go broke within five years of retiring from the league. Each new tale of a player filing for bankruptcy breaks Bridgeman's heart. "Unless you grew up in a family where someone owned a business or you sat around the kitchen table talking about the business page more than the sports page, you have no idea what $10,000 or $100,000 really means," he says. "You may be viewed as rich, but it's not wealth."
Bridgeman, now 60, who briefly owned a minority stake in the Sacramento Kings, was lucky to bend Fitzgerald's ear when he did. Now he chuckles at the owner's jokes—but for Bridgeman the enduring punch line is how someone who knew so little about businesses turned into someone who runs so many.