Feature

The Anti-Boss

Where are the tabloid heroes of yesterday?

Add Comment

By Deborah Mitchell

Howard Spira has not lost his talent for drama. The onetime gambler, who became a central figure in the bitter feud between George Steinbrenner and former Yankees star Dave Winfield, was convicted in 1991 of trying to extort $110,000 from Steinbrenner. Today, Spira is back in the Bronx after serving 26 months in federal prison. He doesn’t go to games, although he’s got an opinion about the Boss’s quest for a new ballpark. “It’s just extortion,” says Spira. “He’s the ultimate master of it.”

Steinbrenner was suspended from baseball for three years after it was revealed that he’d paid Spira $40,000 -- a payment Steinbrenner initially insisted he made “out of the goodness of my heart,” but which Spira said was in exchange for dirt on Winfield. At the time, Steinbrenner said that Spira “ruined my life,” which is exactly what Spira says about Steinbrenner today.

“I hate this man so much,” says the 39-year-old Spira. “He is preventing me now from having the storybook relationship with this goddess that I’ve dreamed about my entire life.” The woman, named Donaji, is a 26-year-old airline worker he met last year in Los Angeles. “I told her that I would do everything in my power to make life a fairy tale,” says Spira. But it’s been tough going, Spira maintains, because Steinbrenner has made it impossible for him to find a job and support himself.

Spira, a college dropout, was working as a sports-radio stringer when, he claims, he took a job as publicist for Winfield’s charitable foundation (the slugger has denied ever employing Spira). By the late eighties, struggling to pay off gambling debts, Spira contacted Steinbrenner, who was contesting payments he was supposed to make to Winfield’s foundation. When Spira was convicted of extortion, he shocked the court by congratulating the prosecutor. “My father really should have worn a condom,” Spira said at his sentencing. “He did not deserve Howard Spira as a son.”

Spira had networking opportunities in prison (where he served with Sol Wachtler) and in a halfway house (where Leona Helmsley also resided), but he hasn’t held a job since a post-jail stint answering phones for his attorney. He wrote a book, Storm in the Stadium: The Truth Never Told, but has been unable to interest a publisher.

Not that he’s been entirely forgotten. After the 500-pound beam fell at Yankee Stadium, a New York Post columnist joked that an “H. Spira” had been arrested for owning demolition equipment. “I was furious,” says Spira, who had his attorney write the paper a letter. Spira is sure that if he could only get a break, maybe land a job as a publicist in L.A., he could turn his life around. “I got all the negatives that went with front-page publicity and not one dollar of the positive,” he says. “I’m frustrated, I’m scared, I’m desperate.” But he’s also still a hero in his own mind. “People have told me that it was because I got rid of George for three years that the Yankees were able to develop, instead of him being Godzilla and trading everyone.”