Steinbrenner agrees to the terms of Dave Winfield’s 10-year, $23 million deal, despite not understanding them.

Dave Winfield Holding Shirt and Cap

Welcome to the relaunched This Day in Yankees History. With the offseason well underway, the Pinstripe Alley team has decided to continue the revived program in its new format. These daily posts will highlight two or three key moments in Yankees history on a given date, as well as recognize players born on the day. We hope you enjoy this trip down memory lane with us!

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This Day in Yankees History (December 15)

40 Years Ago

On this day forty years ago, Dave Winfield became the highest-paid player in baseball after Yankees owner George Steinbrenner signed the 29-year-old slugger and Gold Glove outfielder to a 10-year, $23.3 million contract. It was the beginning of a bumpy and contentious relationship between the two men. Over the next decade, Steinbrenner launched a personal vendetta against Winfield and took extreme measures in a vengeful effort to tarnish Winfield’s reputation.

How did the relationship between The Boss and the Yankees’ new, handsomely-paid superstar so quickly turn sour? For one, Steinbrenner didn’t fully comprehend the contract that he and Winfield’s agent had negotiated. Before becoming a free agent, Winfield had spent the prior seven seasons with the Padres and his new contract included a cost-of-living adjustment to account for his living in New York, where housing and everyday necessities were significantly more expensive than in San Diego. Steinbrenner, in essence, had agreed to Winfield’s contract without understanding its terms.

The ink had barely dried when Steinbrenner started threatening to call off the deal. The two men and Winfield’s agent eventually settled on a compromise by the end of January 1981. In his first season in the Bronx, Winfield hit .294 with 13 homers and 68 RBIs in 105 games in the strike-shortened 1981 season. The Yankees went on to beat the A’s in the American League Championship Series, but eventually lost the World Series to the Dodgers in six games. Winfield’s bat went cold during the Fall Classic, collecting just a single hit in 22 at-bats. Steinbrenner would never forget Winfield’s poor performance in the ‘81 World Series and derisively referred to Winfield as “Mr. May” in several press interviews. By the end of Winfield’s Yankees tenure, Steinbrenner would dislike him enough to take actions that led to the owner’s banishment from baseball.

The Yankees never returned to the postseason with Winfield in the lineup, though he was one of the best players in baseball for the remainder of the 1980s. During the 1984 season, Winfield and his Yankees teammate Don Mattingly waged an exciting and dramatic race to win the AL batting title. Mattingly emerged victorious, finishing the season with a .343 batting average to beat out Winfield, who finished his campaign at .340.

Friendly rivalry: Yankee stars outfielder Dave Winfield; left; and first baseman Don Mattingly ham i

In addition to his contributions as a player, Winfield became the first well-known professional athlete to establish a charitable foundation (inspiring a then-teenage Derek Jeter along the way). He was elected to the Hall of Fame in 2001, his first year on the ballot.