Everyone knows that the Yankees won seven championships in George Steinbrenner’s tenure as owner. Besides the rings, Steinbrenner’s legacy can best be summarized with his nickname, “The Boss.” He would spend the money to bring in players he thought would make the team a winner. Conversely, if those players failed to perform, he’d send them out of town in a heartbeat. With one such player, however, this was not the case.
Ahead of the 1981 season, Steinbrenner signed Padres outfielder Dave Winfield to a 10-year, $23 million deal. The contract made Winfield, now a Hall-of-Famer, the highest paid player in the league.
Winfield continued to put up All-Star numbers in pinstripes. Despite his production, he failed to come through in the clutch. In his first season as a Yankee, Winfield was a woeful 1-for-22 in a World Series loss to the Dodgers. The Yankees would not make another playoff appearance until 1995. After a poor performance from Winfield in a key late-season series in 1985, Steinbrenner ripped into him:
Where is Reggie Jackson? We need a Mr. October or a Mr. September. Winfield is Mr. May.
The feud between Steinbrenner and “Mr. May” came to a boiling point in 1990. Steinbrenner paid gambler Howard Spira $40,000 to “dig up dirt” on Winfield to ruin his reputation. Commissioner Fay Vincent banned Steinbrenner from baseball for life on July 30, 1990.
Steinbrenner was ultimately reinstated in 1993. The funny thing is, the temporary ban of The Boss may have been one of the best things to ever happen to the Yankees. In his absence, Gene Michael and others allowed promising young players to develop rather than trade them for established veterans. This included the likes of Derek Jeter, Bernie Williams, and Andy Pettitte. Without pressure from Steinbrenner to build an instant contender, Michael laid the groundwork for the late-90’s dynasty that would go on to win four championships in five seasons.
No one can deny that The Boss would do whatever it took to win. At the end of the day, however, it was his temporary absence that helped mold one of the greatest dynasties we’ve ever seen.