The 9 Most Bitter Free Agent or Trade Departures in Sports

most bitter free agent or trade

Jon Lester’s departure from the Red Sox to the Cubs this week doesn’t rank among the most bitter free agent or trade departures in sports, not by a long shot. But you wouldn’t know that by perusing the social media response to his decision not to return to Boston. There are lots of factors that can mitigate a favorite playing leaving, and many factors that can make it worse. A player leaving for money stings a fan worse than a player leaving for glory. A player leaving after a championship is more palatable than a player leaving while in the process of rebuilding. And, of course, there’s the grace with which a player leaves one team to start with another. Was he grateful, or does he instantly put his former team in a dark corner of his career? A bitter departure (for the purposes of this list) doesn’t just need to be felt by the fans. It can be felt by the player as well. There’s lots of ways for a relationship between a team and a player to go sideways. There’s a saying, “All things end poorly, otherwise they wouldn’t end.” That’s not necessarily true, but it sure is here.

Here are the 9 most bitter free agent or trade departures in sport history.

Tags: departures, Jon Lester, trade free agency,