Winfield signs record-setting deal with Yankees

Part of the INSIDE PITCH series
Written by: Janey Murray

One future Hall of Famer in the outfield simply wasn’t enough for the Yankees.

So, on Dec. 15, 1980, they lured another to the Bronx, signing Dave Winfield to a 10-year, $23 million contract – the richest in professional sports history at the time.

By signing with New York, Winfield would join outfielder Reggie Jackson, who had been with the club for the previous four seasons, making the All-Star Game every year in pinstripes and finishing as the runner-up for the AL MVP in 1980.

The Yankees held a press conference at Jimmy Weston’s Restaurant in New York to announce the signing, with former manager Dick Howser, new manager Gene Michael, Jackson, Willie Randolph and the entire coaching staff in attendance.

“I’m pleased and proud that I’ll be part of this organization,” Winfield told the New York Daily News. “I didn’t want to drag the negotiations on this long, but I felt like I had to in order to study all the possibilities.”

Winfield, who had spent his entire career with the Padres, was one of the most sought-after free agents of the offseason. In eight years with San Diego, he batted .284 with 154 homers and 626 RBI. His best season came in 1979, when he hit 34 home runs and tallied 118 RBI while batting .308 and finished third in the NL MVP Award voting.

With the Padres, Winfield played right field and hit cleanup. In New York, both of those spots were already occupied by Jackson. But Winfield remained open to playing a number of different roles for the Yankees.

“I’m not worried about playing right field,” Winfield said. “They have a fine outfielder there already. Left field is something to look into. I would prefer to hit third.”

Though the Yankees offer was certainly hefty, Winfield claimed that the decision to sign with New York was not about the money.

The Indians had made a late offer, and the Mets had pursued him, but he wanted an opportunity to compete for a championship right away – and the Yankees offered just that.

Being in New York also provided plenty of opportunities to expand his Winfield Foundation for underprivileged youth, through which he had bought blocks of Padres tickets for children and families in San Diego.

“The Yankees’ offer was definitely not the highest I received,” Winfield told the Herald-News. “The people of New York were a big part in my coming here. Just walking around the city, people would come up to me and say they hoped I’d be with the Yankees. I knew I’d be appreciated.”

After eight years in San Diego, making the jump to New York would be an adjustment for Winfield. With four years of playing experience in the Bronx under his belt, Jackson had some words of advice for his fellow Cooperstown-bound outfielder.

“To play like hell and put numbers on the board,” Jackson said. “This is the greatest place to play. It can be a lion’s den or it can be Disneyworld. The bottom line is if Dave Winfield hits line drives and drives in runs, it doesn’t matter if he talks or doesn’t talk.”

The transition seemed to go rather smoothly for Winfield, who batted .294 and earned his fifth of 12 consecutive All-Star selections in 1981, while the Yankees captured the AL pennant.

Over nine seasons with New York, Winfield batted .290 with 205 homers and an .851 OPS. He was elected to the Hall of Fame in 2001.

Janey Murray was the digital content specialist at the National Baseball Hall of Fame and Museum

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Part of the INSIDE PITCH series