Almost Every Major League Baseball Team Is Probably Going To Regret What They Just Did

By Sean Millerick

There’s an old saying in baseball: flags fly forever.

It’s a maxim that’s never better on display than during trade deadline season. Prospect chips are being pushed to the center of the table to get extra ammunition as teams decide just how much of their future to sacrifice for a present-day title chase. Many fans might even tell you that this is the most exciting time to be a baseball fan…although I would humbly submit that those fans need to get out more. Still, it’s hard to deny that something is fascinating about watching all the dominoes fall every July. If your team is trying to win, it’s high theater. If your team is being strip-mined for parts, it can feel a bit like watching a trainwreck.

Either way, you aren’t looking away until the deadline expires.

Unfortunately for all those teams making splashy moves, though, only one team gets to win the said championship. So just by the law of averages alone, that seems like it would translate to every buyer but one having some degree of regret over their decisions. Now as for when that sense of regret sinks in? That’s anyone’s guess. Could be next week, could be next fall, could be next election cycle. At the end of the day, most teams are going to regret what they just did. Certainly, most of the buyers are.

That could even include the eventual 2024 champion.

Ultimately, it all comes down to which Aroldis Chapman you’re getting.

Way back in 2016, the Chicago Cubs once blew up their farm in a blockbuster deal to bring the flamethrowing Chapman to the Friendly Confines. The result was the end of the Curse of the Billy Goat, a historic feat that would absolutely not have happened without Chapman’s brilliance. No regrets allowed then, no matter how helpful Gleyber Torres would have been to future Cubs rosters.

Aroldis Chapman and David Ross celebrate clinching the NLDS in 2016.Photo byRon Cogswell

Fast forward seven seasons and Chapman found himself being traded once again to the eventual World Series champion. This time though, while good in the postseason, it would be hard to argue his services were essential to the Rangers snapping their own title drought. Especially when you weigh in the cost- Cole Ragans. How much do you think the 2024 Rangers wish they had Ragans in their rotation right now? Texas would very likely be buying right now, not deliberating between selling or standing pat.

Now, the possibility of blowback like this is somewhat less than it used to be. Front offices have become much more covetous of their prospects. Gone are the days when a No. 1 prospect is shipped out for a rental reliever, such as when the Miami Marlins dealt Adrian Gonzalez for a half summer of Ugueth Urbina. The Marlins probably wouldn’t have won it all in 2003 without him, but he wasn’t exactly rock solid in October…and the impact Gonzalez could have had on those 2005 to 2008 Miami lineups is scary to think about.

Would the Marlins have been better off as a franchise having made an extra playoff run or two as opposed to picking up that second championship? Every franchise has plenty of examples like that one, be it that deal, or any of the others you can find enshrined in this David Schoenfield piece from 2019. I’m too young to remember when the Tigers decided trading away John Smoltz was a good idea (they must have evaluated him strictly on broadcasting prowess) but I do recall getting a good chuckle out of the Nationals moving Cliff Lee and the Orioles moving on from Jake Arrieta.

Again, teams are smarter now as a rule. Far more front offices are content to play the long game and avoid the risk of…well…of ending up being lampooned in pieces like the Schoenfield one featured above.

Still, that doesn’t keep GMs from ending up with egg on their face every year. Some of these players will struggle with the scenery change. Some of them will be great for a couple of months, sign an extension, and then revert to something not worth the money. Without question, some of the prospects given up will end up becoming household names…while the veteran that came back will end up being the next cautionary tale.

Who will it end up being?

Stay tuned for coverage of the 2025 MLB Trade Deadline. By that point, we should have a few more big regrets to add to deadline history.

Sean Millerick is a diehard Miami Marlins fan but still finds cause for hope every Spring Training. He currently writes for @CallToThePen. You can find him on Twitter, or whatever Elon wants to call it, @miasportsminute.