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Tim Anderson’s retirement came far too soon for the former White Sox star

Tim Anderson was once the future of baseball. Now he's retiring way too early
IMAGN IMAGES via Reuters Connect

Former Chicago White Sox shortstop Tim Anderson announced his retirement from baseball earlier this week. Coincidentally, it's the same week as the annual Field of Dreams game. You know the game -- it's played on a relatively newly constructed ballpark that's adjacent from the set of the movie Field of Dreams in Dyersville, Iowa.

Most of us remember that the White Sox hosted the New York Yankees in the inaugural Field of Dreams game five years ago during the 2021 season. Most of us remember that Anderson hit a walk-off home run in the bottom of the ninth to power the Sox to wild win over the Yankees, with a final score of 9-8.

Anderson’s greatest White Sox moment now feels bittersweet

It was a great moment for White Sox fans. Rare is the regular-season game where you remember where you were five years later -- but I do and I bet most Sox fans do. What I remember even more, though, is that the moment was touted by pundits as one where a rebuilding Sox team, and Anderson in particular, had arrived. Broadcaster Joe Buck said Anderson should be the face of baseball.

We all know what followed. The 2021 Sox got knocked out of the playoffs by the Houston Astros. The rebuild fell apart over the next few seasons, and the Sox ended up setting records for losses in a season and blowing up the rebuild and starting over.

We know about Anderson suffering a knee injury in 2023 that limited his offense, and we know about his on-field fight with Jose Ramirez of the Cleveland Guardians -- a fight that Anderson would've lost decisively if it were boxing.

We watched the Sox buy out the former All-Star and batting champ as his performance declined, and we watched as he tried to save his career in Miami in 2024 and with the Los Angeles Angels in 2025. He was unsuccessful.

He will now retire as a White Sox, and he'll be celebrated in September. That's nice. He should still be playing somewhere. He's just 33 years old.

Some of Anderson's failure was his fault, there's no doubt. He had off-field issues we won't get into here, other than to say he made some objectively bad decisions.

And some of the on-field stuff wasn't great, either, whether it was directing a slur at a Kansas City Royal or picking the fight against Ramirez. Anderson was a high-energy, emotional player, and occasionally his emotions led him astray.

The White Sox failed Anderson as much as Anderson failed himself

He also may not have had the help he may have needed. Chicago sportscaster/podcaster Dan Bernstein suggested the hiring of an out-of-touch Tony La Russa as manager after the 2020 season may have been detrimental to Anderson -- he may have needed mental-health help, and that need may have gone unnoticed by a checked-out La Russa. Bernstein cautions we can't know for sure, since we weren't there behind the scenes, but the apparent lack of assistance for someone who may have needed it is yet another reason that the Tony La Russa hire was disastrous. There's no guarantee that the rebuild would've succeeded with a different manager, especially given the injuries to Anderson and Luis Robert and Eloy Jimenez, but the TLR hiring hamstrung the rebuild at a critical moment.

Back to Anderson. As I noted above and Bernstein noted on his podcast, Anderson had agency and made bad choices, and that can't be excused. Maybe he'd have made better choices if he'd had help, maybe not, but only Anderson is to blame for his off-field actions. Still, I have to wonder -- if Anderson had some guidance, maybe he'd either have made better choices or dealt with the fallout of his own actions better.

As a Sox fan, I've obviously been bummed to see a promising rebuild fail. Yes, the Sox have restarted the process and the results seem good so far, but I hated watching a promising roster fall apart while the losses piled up. It's not all the fault of La Russa or former GM Rick Hahn or owner Jerry Reinsdorf or the training staff, but all of them had a hand in it.

When I think of the failed rebuild, I think of what could've been and I get sad. That happens when I think of the fates of various key players like Jimenez and Robert. But it goes up a level or two when I think of Anderson.

Anderson made it clear at his retirement press conference how much pain he was in, and how the game of baseball was part of that. That was hard to read and hear.

I don't excuse his off-field actions or his less glamorous on-field moments. That's on him. But regardless of what is and is not Anderson's fault, it's hard to see a player with that much talent, and, on occasion, that much joy, hanging up his spikes five to 10 years before he should.

Forget for a second the larger White Sox project and its failure. Watching a player of that caliber self-destruct while also having apparent difficulties with his mental well-being, to the point he has to exit the sport while in his prime, should sadden us all.

Tim Anderson should still be playing, if not for the White Sox than for some other MLB team. Not only should he still be playing, he should be starting. We should be debating whether or not he has a Hall of Fame case. The headline "Shortstop Tim Anderson Announces Retirement" shouldn't have been seen this soon -- it should've waited until the mid-2030s.

That's not the case, however, and it's sad. It will be nice to send Anderson off properly on September 17, but it's a send-off occurring far too soon.

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