Roger Clemens’ incredible career began with 13 seasons in Boston, during which time he won three Cy Young awards. When he hit free agency ahead of the 1997 season, the Sox didn’t make him a good enough offer (sound familiar?), so he signed with the Blue Jays instead.
Clemens won two more Cy Young awards with Toronto, and then another one once they traded him to the Yankees ahead of the 1999 season. It was in New York that he finally got his two World Series rings, too.
David Cone adopted Tiant’s pitching style and played on the Yankees with Clemens. After also being traded from the Blue Jays to the Yankees during the 1995 season, Cone established himself as a dominant pitcher on some of the Yankees’ late-90s championship teams, adding four more World Series rings to his fingers to go with his 1992 bling.
When he reached free agency, the Sox signed the 1994 Cy Young-winner for the 2001 season. He’s now a color commentator for Yankees games and does Sunday Night Baseball broadcasts on ESPN.