On March 23, 1990 — Gambler Howard Spira is arrested for extorting money from New York Yankees owner George Steinbrenner, who paid Spira $40,000 in January, to dig up dirt on Future Hall of Fame outfielder Dave Winfield. Winfield was dubbed “Mr. May” by the Boss after he failed to carry the team to a championship.

Commissioner Fay Vincent bans the Boss from playing any role in the team’s day-to-day operations for 30 months, upon learning about the arrangement with the Bronx gambler.

In a January 6th, 2010 article – Spira will say –
“George Steinbrenner ruined my health, my life, and my reputation. My life is a living hell,” says Spira, a short, slight man with a gray pallor who favors dark, natty suits. “I have no friends, no life and no future. Everything is complete emptiness, loneliness, and misery. Everyone hates me.”

More from the Posts Article –
Back in the 1980s, Spira, now 50, was an unpaid publicist for Winfield and his charity, the Dave Winfield Foundation, as well as a lousy gambler who owed $100,000 to Mafia-connected bookies. He also owed money to Winfield: He had borrowed $15,000 from the player, who Spira says charged him outrageously usurious interest rates.

Spira figured out a way to solve all his problems at once. In 1986, he approached Steinbrenner and said he wanted $150,000, a job with his shipping company and a room in his Tampa hotel. In return, Spira told the Yankee owner that he could give him proof that Winfield had been squandering his foundation’s money on trysts with girlfriends.

Eager for any dirt he could throw on Winfield, Steinbrenner paid Spira $40,000 (their arrangement was first reported in March of 1990 by the Daily News). Spira says he hectored Steinbrenner to fulfill the rest of their deal, but Steinbrenner called his repeated phone calls extortion.

Read More in the NY Post on the story

Steinbrenner’s suspension and constant interference gone leads to the Yankees building the core that will win titles in 96, and 98 – 2000.

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