"Your first name's white, your second is Hispanic, and your third belongs to a black. No wonder you don't know who you are."
—Centerfielder Mickey Rivers, Jackson's teammate with the Yankees
Reginald Martinez Jackson has never been any one thing. He's African-American and generous and Latino and intelligent and loyal and Irish and blunt and Native American and funny and self-confident. A human melting pot. "But to most of the world, and certainly in baseball, I've always been known as the colored kid," he says. If he seemed like an angry black player to some fans and media during his career, that's because he had reason to be. He suffered the indignities familiar to black minor league players of his time in small-town America. "There were definitely times when the team would pull into a town, and we would have to check and see if the hotel accepted black players like Reggie or if the restaurant would serve them," says former Oakland teammate Joe Rudi, who played with Jackson in both Modesto, Calif., and Birmingham. "Obviously those are the kind of experiences that you can never really forget."
Jackson has a deep appreciation for the players of color who came before him, especially the African-American stars. When he left the Orioles—to whom he had been traded in April 1976—to join the Yankees, the uniform number 9 that he had worn in Oakland and in Baltimore already belonged to third baseman Graig Nettles, so Jackson wanted to switch to 42 in honor of Jackie Robinson. That number had already been assigned to pitching coach Art Fowler, so Jackson took 44 because it had been Hank Aaron's number.
The colored kid now looks out for kids of color; his Mr. October Foundation for Kids is dedicated to creating opportunities for underprivileged students—through scholarships and cash grants to a variety of organizations, including school districts, charities and other foundations—in technology and the sciences. The foundation is just one of his outside interests; the thing that seems to rankle Jackson more than anything is the idea that he is just one thing. "I never wanted to be just Reggie the ballplayer, anymore than I want to be just Reggie the car guy now," he says.
He's also Reggie the businessman, who has relationships with several FORTUNE 500 companies, including the German software corporation SAP AG, and who can talk about debt-to-equity ratios as expertly as he talks about carburetors and camshafts. "I figure I have about 20 years left," he says, "and there are some things I want to do." One of them is to become a baseball owner, which he has tried to do on several occasions, including in 2004, when his group of investors lost out to Lew Wolff in a bid for the A's, and earlier this year, when the group fronted by Magic Johnson beat out Jackson's group, among others, for the Dodgers. There was a time he would have raged about this, maybe gone to the press with a stinging rant. Now? "Patience," he says. "I guess it wasn't time."
"Mark Twain said that politicians, old buildings, and prostitutes become respectable with age. Reggie Jackson would like to make it a foursome."
—Thomas Boswell in How Life Imitates the World Series (1982)
It's not hard to draw a parallel between Jackson and the expensive cars he restores and collects. Like his autos, he is a classic from another era. He's had some bodywork done, but get him revved up and his engine is still powerful. "[The Seaside warehouse] is about taking something vintage and freezing it in time," says Steve DiMercurio, who helps Jackson buy, sell and maintain the cars in his collection. But Jackson is a classic who is never frozen, who's always changing.
He's glad that he matured enough to make sure his turbulent relationship with George Steinbrenner ended affectionately before the Boss died in July 2010. "Reggie is larger than life," says Hal Steinbrenner. "That's why he and my father got along so well. Those last several years my dad began to mellow, and I think Reggie did too. Their relationship became a little less about the emotion of any given moment and more about the long-term friendship."