1990 | BRONX, NEW YORK – A messy soap opera involving New York Yankees owner George Steinbrenner and Dave Winfield, one of his players, hit the headlines again today with the arrest of Howard Spira. Spira, a small-time gambler and former sports radio station stringer, was arrested and charged with extortion.
Spira was convicted a year later for trying to extort $110,000 from Steinbrenner. The mess ended up getting the Yankee owner banned from baseball when it was revealed that he had given Spira $40,000 to find out some dirt about Winfield. Steinbrenner insisted the money was to help “Howie” get back on his feet.
Steinbrenner and Winfield had been feuding for a number of reasons since Winfield signed a 10-year, $23 million contract with the Yankees that Steinbrenner didn’t feel he quite lived up to. Winfield was upset with Steinbrenner for, among other things, claiming he reneged on a promise to donate $300,000 to Winfield’s foundation. That’s where Howard Spira came in. Spira once worked as a publicist for the Foundation. Steinbrenner paid Spira to find out some stuff on Winfield that Steinbrenner could use against him.
Steinbrenner was reinstated as Yankees owner in 1993. Howard Spira served 26 months in a federal prison for extortion. What’s never been clear is why someone with the resources of George Steinbrenner would seek out someone like Howie Spira rather than, say, an ex-FBI agent.