Mike Lowell actually made his MLB debut with the Yankees in 1998, but only played eight games for them. Nevertheless, he received his first World Series ring that year, before getting traded to the Florida Marlins in February 1999.
After a cancer scare, he proceeded to have an excellent tenure in Miami, including winning a World Series in 2003, before being traded with Josh Beckett and Guillermo Mota to the Red Sox after the 2005 season. In retrospect, it’s funny that Lowell was the contract the Marlins wanted to unload, as he went on to be excellent in Boston, leading them to their second championship in four years. He became just the second Puerto Rican player ever to be named World Series MVP, following in Roberto Clemente’s footsteps.
Jacoby Ellsbury replaced Johnny Damon as the traitor of the century when he departed for the Bronx on a seven-year, $153M contract barely a month after helping the Sox win their third championship in ten years. And unlike Damon, who supposedly tried to stay in Boston, Ellsbury was keen to depart, making him all the more villainous to Red Sox Nation.
However, it ended up working out quite well for Boston, as injuries derailed Ellsbury’s career. By 2018, he wasn’t playing, and by the end of 2019, the Yankees released him. They still owed him $26M for the 2020 season and his buyout for 2021, and attempted to get out of paying it on the basis that Ellsbury had received unauthorized medical treatments.
His contract is now considered one of the worst in Yankees history.