In 1990, only three years after he was done playing, Reggie Jackson joined a group of investors interested in bringing a Major League Baseball team to Phoenix.
Six years later, Phoenix got a franchise but Jackson wasn't involved.
"I was disappointed at the time, but it didn't seem like a major setback," he said. "I thought in time it would happen."
Sixteen long years later, Jackson still isn't involved on the ownership level, and he is discouraged. His latest plan was to try to purchase a share of the Florida Marlins. Owner Jeffrey Loria rebuffed that idea, even though his financially strapped franchise has the lowest payroll in the game.
"It wears you down," Jackson said. "They want to make you tired and quit the game. I admit it; I'm tired now. I'm tired of waiting."
Jackson wants to be a trailblazer. There has never been a black principal owner of an MLB franchise. Arte Moreno, who purchased the Angels three years ago, is the only minority owner.
"All ownership should not be white," Jackson said. "There should be a cross-section. Every Fortune 500 company isn't run by a white person. Why is every baseball team? Why don't more people ask that?"
Jackson twice tried to buy the Athletics, once with the intention of moving them to Las Vegas. He also tried to get involved with the Dodgers and Angels when they were made available, and he made an unsolicited offer to purchase the Twins. He claims the investors he represents have enough financial capital to purchase any team in the game.
"It's not a financial issue," he said. "You can always find people who want to buy into a team. It's getting in the door that's tough."
Jackson accuses commissioner Bud Selig of blocking his entrance into the game's penthouse suite.
"There's one guy with one key," he said. "One guy, one key. That says enough. I've talked to Selig on several occasions. Nothing comes of it."
Rich Levin, MLB's senior vice president of public relations, said baseball "would love" to have a black managing partner.
"There has to be a club for sale," he said. "The commissioner if not opposed to Reggie Jackson by any means. Baseball has influence, sure we do. But (black ownership) is something we want."
Jackson did not get involved with the sale of the Washington Nationals despite the city's large black population. He believed Selig would guide the team to the ownership group of his choice. Ultimately, two competing ownership groups merged, and the Nationals will be owned by Ted Lerner and run by Stan Kasten, a Selig supporter who ran the Atlanta Braves for 17 years.
"Everybody saw that coming," Jackson said. "Of course Kasten gets the team."
Jackson's previous ownership bids have been hurt by his desire to bring a team to Las Vegas, a boundary Selig is not yet ready to cross. It will take another league going to Las Vegas — the NBA, most likely — before baseball follows.
Jackson's best chance could be purchasing a minority interest with an option to purchase a controlling interest. It is unclear what franchise will next become entirely available.
As he waits, Jackson works for the Yankees as a special advisor to owner George Steinbrenner. It's a loosely defined positioned with few actual responsibilities. He says it's the only job he's ever been offered in baseball since he retired.
"A few broadcasting things but that was it," he said. "So I decided I'd rather go right to the top. It became my goal."
He hasn't gotten there. At this point, he doubts if he ever will.