Yankees History: Howard Spira Arrested for Extortion

The George Steinbrenner Era had its unique moments. One of them came on this day in 1990, when Howard Spira, a professional gambler, was arrested for extorting money from the Yankees owner.

During the early part of his tenure as Yankees owner, George Steinbrenner ran the team like a demented Roman emperor. Anyone who displeased him was sent away, and he would bring his favorites back. And yet, try as he might, Steinbrenner just could not bring down Dave Winfield, a player that he began to feud with almost from the moment he was signed.

The problem with Winfield was that he had a clause that adjusted his salary for the cost of living. His salary, already the highest in the league, would increase by $8 Million over the ten year life of the contract. As such, he was desperate to bring Winfield down, with lawsuits between the two sides and attempted trades.

That desire to destroy Winfield came to a head in January 1990. Howard Spira, a professional gambler by trade, had been an unpaid publicist with the Winfield Foundation a decade prior. Now that he owed $100,000 to various bookies, he approached Steinbrenner and claimed he could prove that Winfield used foundation money on his various girlfriends. For that information, Steinbrenner paid him $40,000.

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However, Steinbrenner refused to pay anything further to Spira. He accused Spira of trying to extort money from him, and on this day in 1990, Spira was arrested. However, the explanation as to why he paid Spira that first $40,000 would change, from threats about his family to “the goodness of his heart.”

Eventually, the truth came out and Steinbrenner’s vendetta was exposed for all the world to see. Not only did he fail to destroy Winfield, but he made the outfielder a sympathetic being.

In fact, Steinbrenner’s legacy was almost destroyed. He would be sent into a lifetime suspension, which eventually became a two year ban. Winfield himself was sullied a bit, needing to pay approximately $230,000 back to the foundation. He had also loaned Spira some money back in 1981, despite his original denials of such. Spira, meanwhile, spent 22 months in jail, and blamed his issues later in life on Steinbrenner selling him out.

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George Steinbrenner sought to destroy Dave Winfield. Instead, the Yankees owner found himself under scrutiny.