to “known gambler” Howie Spira in exchange for “dirt” on Dave Winfield.

The Yankees signed Dave Winfield to a then-record 10-year contract after the 1980 season, but before the ink dried, Steinbrenner and his new outfielder seemed destined for a decade of confrontation. One of the main points of contention was a $3 million pledge Steinbrenner made to the Dave Winfield Foundation. Throughout the 1980s, the promised contribution was a major source of friction between Steinbrenner and Winfield as the two parties squabbled over the timing of payments and the foundation’s use of funds. The disagreement culminated in dueling lawsuits before the 1989 season, but the two sides eventually struck a deal before arguments were put before an arbitrator. However, despite the resolution, the events leading up to itwould eventually come back to haunt Steinbrenner.

During the 1986 season, Steinbrenner and Winfield’s feud had become well publicized, and Spira, who had his own axe to grind against the All Star, decided to take advantage. The gambler, who was also a disgruntled former employee of Winfield, offered to provide Steinbrenner with damaging information about his one-time boss in exchange for financial assistance. Because of the eventual arbitration settlement, Steinbrenner never needed to use the dirt Spira had provided, but the gambler still insisted on his payoff. After angling for a job with Steinbrenner, Spira eventually accepted a $40,000 check, but then, not long after, demanded more. Those demands would become the basis of Spira’s extortion conviction, but much to the dismay of Steinbrenner, they would also lead to