There was a gambling scandal on the horizon. I read that he left to escape the problem. But the league needed him more than they thought.
Guys who stayed too long would qualify: Willie Mays, Steve Carlton, Craig Biggio.
Both of whom today have all their mental faculties and can walk without canes. Those may not have been the best decisions for their fans, but for themselves and their families, they were just fine.
The Lions were gutting the Detroit offensive line to save money. Barry objected to that. they left him by himself way too often. Barry understood he was going to take a beating for a team that was not trying to win the championship.
I had season tickets for his entire career. I also had them when he retired. They would not return my money.
Muhammad Ali hung on too long.
I give Sanders, Jordan, and Brown a pass–they left on their own terms, with their health intact.
Mays wasn’t all that bad. He was asked by the team to stay on an extra year and did so. He was also better than any other center fielder (Don Hahn, had only a slightly better BA, a lower OBA, hit fewer HRs and had an OPS 75 points lower) the team had available, and had a successful postseason. He wasn’t Willie May (and evidently, he missed a fly ball one time that has been repeated over and over as a sign of his decline), but he did not really embarrass himself on the field.
But he does not deserve to be called this, since he was just staying on because the team basically begged him to.
Mays wanted to go back to play in NY where he started so that’s why he went to the Mets.
I’ve always had a highly dim view of athletes who had a chance to accomplish extraordinary things and make an indelible mark on history, but squandered it doing stupid crap. Stupid crap which, incidentally, even if they absolutely had to do it, could’ve easily waited until their playing careers were over.
In that vein, I’d like to nominate Asashoryu as #3. Who? Exactly. A Mongolian sensation who shot up the ranks of Japan’s most venerable sport, sumo. He won an astounding 23 championships before age 30. Among those in the know, it was an absolute given that he…a foreigner!..would break Taiho’s record of 31 championships, and the only question was by how much.
And then, the first torubling sign, cutting out on an exhibition tour for a soccer tournament in his native Mongolia (and faking an injury to do this). He was a yokozuna. He was a living embodiment of the sport. This was not acceptable. You’d think he could’ve fired off a memo to his hometown buddies saying, “Look, sorry, I’m kinda busy right now”? Suspension, missed tournament.
And then that stupid, stupid bar brawl which ended his career cold.
Slumming in at #2 is James “Buster” Douglas. Remember him? 1990? Faced down the invincible juggernaut monster and beat him? In a sane world, this would’ve led to an epic, years-long rivalry against Evander Holyfield and vaulted both him and the sport into the stratosphere. What happened was that he neglected his training, went into the Holyfield fight out of shape, got clobbered, and prompty vanished off the face of the earth. (He did have a nice little nostalgia run years later, after boxing’s popularity had dipped to somewhere between curling and competitive face slapping, but nothing came of it.)
And #1, easiest choice here…Anna Kournikova.
Just reflect on what she did. She used a fledgling medium (the Internet) to get hordes of drooling horndogs interested in tennis. Just think about how epic that is. We’re talking a once-in-eternity event here, like the atomic bombings of Hiroshima and Nagasaki and the collapse of the USSR. This is a woman who, by dint of happening to be ravishingly sexy and a pretty good tennis player, was doing for her sport what Wayne Gretzky, Lance Armstrong, and Tiger Woods did for theirs.
Just one little problem, though: Although she was a fine doubles player, her singles game left something to be desired; in fact, she had never won a singles title. And getting good enough to contend in singles would require sacrifices of time and effort which would inevitably require to cut back her modelling and PR schedules. Around 2001, her game was really starting to suffer due to lack of proper training and too many distractions.
At this point, she had two realistic options. Become a doubles specialist, which would require a less demanding training regimen. Or drastically cut back her second job and work on developing her considerable raw skills, thus salvaging her flagging career.
Instead…she didn’t change a damn thing. Her body completely fell apart, and her game soon followed, culminating in a memorable first-round tumble at the US Open. Her schedule was drastically cut in '02, and somewhere in '03 she quietly faded out with no fanfare whatsoever.
Ah, well, nice when it lasted, now she can model and schmooze and flirt full time, right? Turns out that without her tennis career, she’s just another overprivileged high-maintenance prima donna. Heck, Paris Hilton can at least sing! (Allegedly.) The sports magazines and channels completely forgot about her. Russian hockey players lost interest, and the gossip rags soon followed. The drooling horndogs moved on to fresh meat. A lesson which hit her harder than most…once you’re over 21, nobody gives a damn anymore.
I don’t think that counts in the way the OP described, personally. That’s more sad than pathetic. But if we’re going that route, why not Bill Masterson of the North Stars, or Ray Chapman of the Cleveland Indians?
Wait … wasn’t he motivated to do that by the unexpected murder of his father? I can certainly understand how that might move someone to make a radical life change, particularly a multi-millionaire at a point that he’s only doing the job to amuse himself. What makes it the worst ever?
(I could easily be wrong about the father-murder thing.)
Yeah, I saw a documentary on his ill-advised baseball career on TSN a few weeks back. His dad and him had concocted the plan for sometime, but he finally decided he had to give it a try after his father was murdered. Certainly speaks to a sense of filial duty, which earns him points in my books, even if it is a stupid idea.
The people who were very happy Jordan played baseball were all the team owners who sold a lot more tickets when he came to town. Also his teammates since he bought them a fancy new bus to travel in.
Roberto Clemente.
I think it’s time we stop saying that athletes who died suddenly had “embarrassing” retirements, which is what the OP asked for… it may have been embarrassing for the organization, as in the case of Konstantinov mentioned above, but Clemente, any of the boxers who were killed in the ring, and Ray Chapman never retired.
Personally, the one that always stung the worst was Chris Sabo. I was a Reds fan growing up, and Sabo was one of my favorite players. He came back to the Reds in '96, but got busted for using a corked bat and retired at the end of the season. The last image I remember of Chris Sabo is him laughing as he was getting ejected from the game in which his bat broke. It was just sad to me.
Wanted to clarify: Konstantinov’s death was embarrassing for the Red Wings organization only in that it was a team outing… they weren’t in any way responsible for his death.
Especially since he isn’t dead.
The OP’s title asked for “worst” retirements, which is what those replies are answering.
How about Ricky Williams? He retired in 2004 to go smoke weed for a year, then returned in 2005.
Actually, that may be the best retirement in sports history! 
He also was going to miss 4 games that year due to smoking pot.
No, it completely stunk!
(Was late to my fantasy draft that year, and the Yahoo auto-draft drafted him first for my team.
What made it so terrible is that Yahoo’s craptastic fantasy football system neither removed him from the draft list OR from the “do-not-cut” list, in spite of his “retirement” about a week earlier.
So I was stuck with Doob McPothead on my team, on my do-not-cut list for the entire season, and to add insult to injury, the computer picked him first!
Good one. He was a jerk/iconoclast (depending on your views) but he had it all…he could’ve coasted to mega-greatness.