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Yankees: 4 best deals in MLB Winter Meetings history

By Adam Weinrib

NEW YORK - NOVEMBER 04: C.C. Sabathia of the New York Yankees celebrates in the dugout with a copy of the New York Post after their 7-3 win against the Philadelphia Phillies in Game Six of the 2009 MLB World Series at Yankee Stadium on November 4, 2009 in the Bronx borough of New York City. (Photo by Nick Laham/Getty Images)
NEW YORK - NOVEMBER 04: C.C. Sabathia of the New York Yankees celebrates in the dugout with a copy of the New York Post after their 7-3 win against the Philadelphia Phillies in Game Six of the 2009 MLB World Series at Yankee Stadium on November 4, 2009 in the Bronx borough of New York City. (Photo by Nick Laham/Getty Images) /
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CHICAGO – 1986: Dave Winfield of the New York Yankees bats during an MLB game versus the Chicago White Sox during the 1986 season at Comiskey Park in Chicago, Illinois. (Photo by Ron Vesely/MLB Photos via Getty Images) /

2. Yankees Trade for Dave Winfield

The Yankees pulled off a coup when they brought Hall of Fame outfielder Dave Winfield from San Diego to the Bronx.

Looking at Dave Winfield, it’s no wonder the monstrous outfielder was originally drafted out of Minnesota by both NFL and NBA teams.

A borderline tight end in right field, Winfield had a rifle for an arm and a penchant for the long ball, cranking 37 home runs in his first full season in the boogie down in 1982 (thanks so much, 1981 strike!).

Winfield inked a remarkable 10-year, $16 million contract following the 1980 season, just a few days after the Mets (!) had raised the bidding to $1.5 million annually and the Indians had also tried to pry the 29-year-old away from San Diego. No dice — George Steinbrenner usually prevailed in those days.

Winfield never won a ring in the Bronx, unfortunately, only playing in one postseason in his very first year in pinstripes and hitting .045 in the World Series against the Dodgers, leading to the ignominious nickname “Mr. May” courtesy of Big Stein.

All in all, though, you don’t turn down a Hall of Famer when you see one; Winfield collected a ring with the 1992 Blue Jays anyway. Even Steven.

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