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.
Fav-ruh would rank higher on this list, but the stakes weren’t as high as they would have been earlier in his career. He went to the Jets, who don’t’ really have any sort of relationship good, bad, or otherwise with the Packers. And the notion of Brett Favre in Manhattan was more bizarre than it was frustrating. However, I don’t think anyone on this list was more important to a fan base (save for Gretzky), so seeing him traded for a 4th round pick was a tough pill to swallow.
9. Brett Favre
This is a huge one, and for the sake of the list, we’ll call this a “free agency” move. With the luxury of hindsight, this move may have gotten less divisive over time, but that’s true for most of the entries on this list. The scope of Saban’s betrayal wasn’t just his departure from LSU and college football. It was also his return to the SEC once his NFL career failed to take off in Miami. He came across as a hired gun just looking for the best available deal. Many coaches and players probably have that instinct, but they disguise it far better than Saban did.
8. Nick Saban
I can’t really speak to the temperament of Red Sox fans 100 years ago when this happened, but considering that even the ones NOW will still get wound up about this, I’m going to hazard a guess that they weren’t thrilled. So when you take in a century of anger and frustration (at least until 2004) about Ruth and his sale proceeds going to fund a musical (!), yeah, we’re comfortable putting him here. It would rank higher, but I don’t think sports fans were quite the savage animals they were in 1919.
7. Babe Ruth
There’s not terribly compelling backstory to this one. Pujols was the savior of the most baseball-crazy town in the universe, St. Louis, and he packed up his stuff and headed to Anaheim, where three out of ten people can pick a baseball bat out of a lineup. The motivation was money, pure and simple. And while Anaheim had flirted with success before and since, it’s not St. Louis. And the Cards fans didn’t have to be arrogant to understand that. It’s hard to explain to passionate fans the virtue in leaving them for a $20 million instead of staying for $18 million or…whatever. That’s a much smaller psychological gap than $2 million to $4 million, even if the size of the difference is the same.
6. Albert Pujols
Roger Clemens didn’t manage to just burn bridges as his career plodded on, but he pissed on the ashes as well. Not known for being charismatic, well-spoken, or anything other than a great pitcher, the Rocket refused to resign with the Sox despite their claim that they offered him more money to stay than they’d ever offered anyone before, despite seeing that point in time as the “twilight of his career.” They were wrong about that part, as Clemens went on to kill it with the Blue Jays, then took off to New York, which went over like a lead balloon for Sox fans. His ungrateful nature and general crappiness later on didn’t help matters.
5. Roger Clemens
This one gets points for being recent. And for being terrible. Strangely enough, a defector’s success after leaving has a big impact on how that departure is viewed. LeBron won titles and that stung worse. Lane Kiffin just flat out failed after breaking a promise (as I see it) to Vols fans and heading to sunnier, greener pastures in Pete Carroll’s absence at USC. He sucked at USC and is now working under the employ of Nick Saban in Alabama, which seems about right.
4. Lane Kiffin
There are a lot of heartbreaking departures that have embittered fans because that athlete is a local favorite, or has a longstanding tie to the team. Carlos Boozer wasn’t really anyone’s favorite, but the way he bugged out of Cleveland for Utah is one for the record books that just gets added to the pile of “terrible things that have happened to Cleveland fans.” Boozer reportedly had committed to the Cavs to resign, but needed to be let out of his current contract to do so. The Cavs, having the right to keep him for one more year for a pittance, let him go to resign him for an agreed-upon amount. He then accepted a higher offer in Utah, claiming he made no commitment. Gross.
3. Carlos Boozer
Does it need to be discussed? It wasn’t what he did, which was heartbreaking, but understandable, but the manner in which he did it. There’s never been a more heartbreaking, agonizing departure from a city as there was via The Decision. He’s back now, and history will likely show that he’s forgiven, but the most angry reaction ever was when LeBron left Cleveland.
2. LeBron James
Sure, social media wasn’t a thing when Wayne Gretzky got sold to LA from Edmonton, but every factor was just right to make this the most bitter departure ever from a town/team. He was the biggest player in hockey history, arguably at the peak of his career, representing a tiny town in western Canada, and he sent to LA, a godless hockey outpost with no respect for anything. It came as a total shock, two hours after they won a championship. And all the Oilers got was some cash, not even for their team, but for their owner’s other ailing businesses. It doesn’t get much worse than that.