Dave Winfield

In 1978, Winfield met the aggressive Albert S. Frohman, a retired businessman who would become his agent. Frohman encouraged Winfield to leave the Padres and move up to the New York Yankees. He managed to get Winfield a ten-year contract with the Yankees, a $1 million signing bonus and regular contributions to the Winfield Foundation. The deal also included a cost-ofliving pay increase, which Yankee owner George Steinbrenner later said he had not fully understood at the time of the contract. The deal was signed on December 15, 1980. Things seemed to go wrong from the time Winfield signed it.

Unhappy with the costly contract, Steinbrenner began to insult Winfield in the media. When he failed to perform well in the 1981 World Series, Steinbrenner called him "Mr. May," in contrast to former Yankee Reggie Jackson, whose World Series game hits were so outstanding he had earned the nickname "Mr. October." Steinbrenner also stopped making his agreed-on contributions to the Winfield Foundation, but Winfield sued his boss to get the money owed the organization.

In addition to these actions, Steinbrenner tried several times to trade Winfield, but his contract gave him the ability to veto the trades. Managers and coaches were fearful of praising Winfield's performance in the media, believing it would anger Steinbrenner. The fans, however, were pleased with the fact that Winfield got at least 100 runs batted in every year for five years. He was the first to do so since Joe DiMaggio. Winfield's struggle later came out in his autobiography, Winfield: A Player's Life, which is said to have infuriated Steinbrenner.

In addition to troubles with his boss and the team, Winfield faced personal assaults during the Yankee years as well. In the mid-1980s a woman took him to court for support of her daughter, of whom Winfield did not deny paternity. He later came to establish a good relationship with the girl. In 1985, another woman sued Winfield, claiming he had given her venereal disease; this was settled out of court. Around the same time, an investigation was launched into the Winfield Foundation's finances, for alleged wrongdoing.

Through the troubles, Winfield continued to play his best baseball, batting .322—the fourth highest in the American League—in 1988. Rarely succumbing to injury, Winfield in 1989 had surgery for a herniated disk in his back and missed the entire baseball season. The following year, after a decade with the Yankees, he was traded to the Anaheim, California, Angels.