MARCH 23: STEINBRENNER, WINFIELD & SPIRA

TODAY IN BASEBALL TAKES US BACK TO THE BRONX, NEW YORK MARCH 23, 1990. The Steinbrenner – Winfield – Spira soap opera hit the headlines again today. Howard 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 New York Yankees owner George 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 some dirt on Dave Winfield, one of his former players.

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, 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 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. It was all part of the Steinbrenner Winfield Spira soap opera.

Contributing sources:
ESPN.com
DeadSpin