6 offseason decisions the 2026 Yankees are paying for in August

Hindsight is definitely 20/20, but as we sit here in August with the New York Yankees' hopes of winning the AL East crown dwindling, it's fair to look back at a few of the club's offseason decisions and wonder how much they've contributed to the team's current fortunes.

Some of these moves we may have even agreed with at the time. Hey, we can be wrong, too! It's okay for a team to have a good process that somehow yields bad results every once in a while. Bad process bringing about bad results, though? Well, that's a recipe for disaster.

Yankees are regretting these offseason moves after 2026 trade deadline

Letting Cody Bellinger and Scott Boras dictate their offseason workflow

This one's a little meta, but at the same time, it had the single greatest impact on how things worked out for New York over the winter. The Yankees waited around for Cody Bellinger to make his decision while Scott Boras led them around by the nose. In the meantime, other free agents that could have filled New York's needs signed elsewhere as the club was frozen in place.

That doesn't mean bringing back Bellinger wasn't a good idea, but he's on the shelf now in August, and the offense is struggling. Perhaps the Yankees' fortunes would have been better if they didn't allow him to paralyze their offseason activities.

Trading TJ Rumfield for Angel Chivilli

For many, this seemed like a move that was mostly inconsequential. TJ Rumfield was about to turn 26 and was not a highly ranked prospect. He also had no clear pathway, at the time, to regular playing time with the Yankees. At the same time, Angel Chivilli was nothing more than a shot in the dark, but New York needed more reliever depth, and he had a big arm with a lot of youth to dream on.

Chivilli has shown flashes in small spurts, but Rumfield has blossomed in Colorado and could be a dark horse NL Rookie of the Year candidate. He's not just a byproduct of Coors Field, either, with a .798 road OPS compared to an .851 home mark. The Yankees ended up trading for Luis Garcia Jr. at the deadline, but he would have been unnecessary had they simply held onto Rumfield. Maybe some foresight regarding the likelihood that Giancarlo Stanton would get injured would've helped here.

Trusting Jasson Dominguez too much

The Yankees needed a right-handed bat for the outfield, but their plan seemed to be trusting Jasson Dominguez to figure out left-handed pitching, while also taking a flier on Randal Grichuk once spring training was around the corner. Grichuk has since proven that New York's quick trigger was premature. Can't blame them for that, though. He didn't look good at all.

An even better move, though, would have been to pick up an option that provided greater certainty than Grichuk, and even capitalize on Dominguez's remaining trade value before it turned to dust at this year's trade deadline. The Martian is clearly no longer a part of New York's future plans, and his value is almost nil. That's the even bigger takeaway here.

Extending the qualifying offer to Trent Grisham

One of the great mysteries of the modern world is whether or not the Yankees believed Trent Grisham would accept the qualifying offer, and if they were okay with forking over $22 million into his pockets. Either way, it seems like a bad move now.

While most were concerned about Grisham's bat regressing, the more pressing issue at this point in time is his extremely poor defense. There's a world where Cody Bellinger could have covered center field until Spencer Jones was ready, and the Yankees could have spent that $22 million on other needs like bullpen help or a right-handed hitting catcher.

Going into the season with two left-handed-hitting catchers

While there was still hope that Austin Wells could be an impact hitter at the plate, the idea that he and J.C. Escarra, both left-handed bats, was good roster construction was a bit ridiculous. Add in the fact that the emergency third catcher, Ben Rice, also hits left-handed, and it becomes laughable.

Ali Sanchez has been okay, but he's a below-average hitter who has also made some serious defensive gaffes. A stable veteran backup who could hit right-handed pitching would have been a simple and obvious move. Well, obvious to most, that is.

Not adding a single experienced reliever

The Yankees' bullpen struggled mightily for most of last season, and post-trade deadline things were even worse. Brian Cashman's solution was to ditch Devin Williams and Luke Weaver and replace them with Cade Winquest and Angel Chivilli.

Here we are in August, and Jake Bird is in Washington. Camilo Doval is in Pittsburgh. Hitters have figured out Tim Hill, and Fernando Cruz is hitting a wall. No one could have ever predicted that this would happen.

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