Bidding adieu: Baseball’s most bittersweet goodbyes

Did Sandy Koufax have the greatest career ever cut short? The evidence is overwhelming.

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You just never know when the time will come that you have to hang up your spikes, pack up your equipment bag for the last time, and walk out of that locker room without looking back again.

Then again, sometimes you do! Some players last long enough in the game that you can see the light at the end getting brighter as the summer shifts to fall and then winter. And it’s not always tragic. Often, you get to see your dreams come true before your eyes before you call it a career.

But this is the baseball offseason, so ’tis the traditional time for MLBers of a certain age and health status to make the final determination of whether to file retirement papers and head to other pastures.

Here then are five of the most bittersweet and premature farewells the last couple of generations of baseball fans have had to endure:

(Note: Sudden [Roberto Clemente] or imminent [Lou Gehrig] deaths have not been taken into consideration here because those goodbyes are tragic and often sudden and not "bittersweet" by any rational interpretation of the word. Onward!)

5. Mike Schmidt

Look, let’s be honest, Schmidt really shouldn’t be on this list. He played his 18 seasons, won his three MVP awards, and finished his career with a 147 OPS+ over more than 2,400 games. (Also, his 106.5 career bWAR, good enough for 26th on the all-time list, knocks me over every time I look it up. Not just sneaky good but sneaky great.)

So what made his exit from baseball so bittersweet? That he did so by delivering what can only be described as the most emotional farewell press conference these eyes have ever seen.

4. Don Mattingly

What silly, rotten luck for the man dubbed Donnie Baseball. For years, Mattingly was the only dependable star on some truly awful Yankees teams of the 1980s and early ’90s. His quite solid career (127 OPS+ over nearly 1,800 games) spanned most of the franchise’s longest stretch of playoff inactivity in 60 years. The year before his debut in 1982, the Yankees went to the World Series. They didn’t return to the playoffs until his final season in 1995, when they lost in a memorable five-game ALDS against the Seattle Mariners. Mattingly hit .417 and posted an OPS of 1.148 in that series but had to retire shortly thereafter at the age of 34, thanks to lingering back issues.

In a plot twist proving fate does has a sense of humor, the Yankees won the World Series the following year and would win three more over the next four. It’s no wonder SI’s Jay Jaffe has called Mattingly "the golden child of the Great Yankees Dark Age."

Maybe he should’ve just trimmed those sideburns after all.

3. Brandon Webb

Webb’s career reads like that of a child star who won Emmys as a teen and was then blacklisted as a 20-something because he lost his ability to act his way out of a paper bag. Or something. He’s basically the Lindsay Lohan of baseball, except for all that scandal and rehab and whatnot.

But consider this: Before he turned 30, Webb led the NL in wins twice, won a Cy Young, pitched more than 200 innings in five of his first six seasons and from 2003 to 2008 had the second-best ERA+ of any pitcher who started more than 135 games (only Johan Santana was better).

And then … kablooey. His shoulder gave out and he pitched his final career game in April 2009, a month before his 30th birthday. After multiple attempts at a comeback, Webb finally retired in May of last year.

2. Adam Dunn

How’s this for a cruel way to go out? You play 2,000 games, a pretty solid (if mostly three-true-outcomey) career. You make it an open secret you’re going to retire at season’s end. You finagle a trade to a team that was, at one point in the season, the hottest in baseball and one that was seemingly destined for the playoffs, the first of your career! And then, when all you have to do is win the one-game wild card to advance to the ALDS, you don’t even get to play — and your team loses. Career over. Your 2,001-game baseball odyssey has come to its conclusion just like that.

In the end, Adam Dunn deserved a lot better.

1. Sandy Koufax

Speaking of pitchers (like Webb) who never pitched beyond their age-30 season, Koufax is the all-time dean emeritus of the College of Early Retirees. Owner of the greatest B-R page in the sport’s history — except for one Barry Bonds, because seriously, come on now — Koufax defied all modern-day expectations of what a pitcher could hope to be.

Try as Clayton Kershaw might — and yes, please do! — we shall never see another like Koufax.

You can follow Erik Malinowski, who always knows the proper time to make an exit, on Twitter at @erikmal and email him at