Jacoby Ellsbury becomes the first major free agent to sign with the Yankees immediately after playing with the Red Sox since Johnny Damon following the 2005 season. Below is a list of notable Red Sox players to become Yankees, either via free agency or trade ... or purchase.
Babe Ruth: Purchased by Yankees from Red Sox (1919)
In December 1919, the Red Sox sold Babe Ruth to the Yankees for $100,000 after he hit a league-leading 29 homers. Over the next 15 seasons, he hit 659 homers with the Yankees, winning four World Series. The Red Sox would not win another title after the trade until 2004.
Sparky Lyle traded to Yankees (1972)
After five seasons as a reliever in Boston, Lyle was dealt to the Yankees prior to the 1972 season for two players. In seven seasons with the Yankees, he turned into a dominant closer and was the American League MVP in 1977.
Luis Tiant signs with Yankees (1978)
In the offseason following 1978, Tiant signed as a free agent with the Yankees after registering 122 wins and three 20-win seasons with the Red Sox. He pitched just two years with the Yankees, winning 21 games total.
Wade Boggs signs with Yankees (1992)
After spending his first 11 seasons with the Red Sox, including eight straight in which he was an All-Star, Boggs joined the Yankees after 1992. He spent five seasons with the Bombers, hitting .313 and helping them win the 1996 World Series.
Roger Clemens traded to Yankees (1999)
After 13 years with Boston and two with the Blue Jays, which included back-to-back Cy Young wins, Clemens was traded to the Yankees in a deal for David Wells. Clemens helped New York win the World Series in 1999 and 2000.
Johnny Damon signs with Yankees (2006)
One year after helping the Red Sox “break the curse” in 2004, Damon signed with the Yankees as a free agent for $52 million. Damon hit .285 and helped them win the 2009 World Series.
Kevin Youkilis signs with Yankees (2013)
After breaking into the majors with the Red Sox in 2004 and spending nine seasons with Boston, Youkilis was dealt to the White Sox during the 2012 season. The following winter, he signed a one-year deal with the Yankees. He played a career-low 28 games in 2013, hitting .219.