Three MLB Teams That Have Had the Most Confusing Offseasons

The Yankees have had a relatively quiet offseason. | Brad Penner-Imagn Images

Contending teams in MLB are in the midst of an arms race. The Dodgers continue to break the bank to load up on talent, having signed the likes of Edwin Díaz and Kyle Tucker, while other teams such as the Blue Jays, Orioles and Mets have been spending big via trades and free agency as a means of keeping up.

Other contenders, however, have taken a more passive approach to the offseason. Whether they were outbid on top targets or simply not comfortable allotting so much money to specific players, there have been a handful of playoff teams or postseason contenders that have yet to truly improve the roster. For fan bases of those teams, it’s been a frustrating few months, forced to remain patient while other organizations make a multitude of signings and trades.

Let’s take a look at some of the teams that have had the most confusing offseasons.

New York Yankees

The Yankees re-signed Cody Bellinger to a five-year contract. | Brad Penner-Imagn Images

What have the Yankees truly accomplished this offseason? Fans were hopeful the team would be aggressive in free agency after the team’s ALDS defeat to the Blue Jays. Thus far, that hasn’t been the case.

New York hasn’t made any marquee acquisitions this winter, outside of re-signing Cody Bellinger, a move which serves merely to bring them back to the same level they were at last season. The team also brought back Trent Grisham via the qualifying offer––a one-year deal worth north of $22 million, which many felt was a steep overpay. Their other moves have been lackluster, such as trading for Ryan Weathers, a former prized pitching prospect with a 4.93 career ERA over five seasons, and reuniting with veteran starter Paul Blackburn.

Yes, the Yankees won 94 games in 2025. It was a solid season until it all fell apart in the ALDS. But to effectively stand pat and not attempt to further fortify the roster is a head-scratching decision from ownership, especially when it feels as if the organization is one or two key moves away from being true contenders once again. There’s still some time for Brian Cashman & Co. to deliver a big move, but they’ve yet to do anything to truly improve the team’s outlook heading into the ‘26 season.

Philadelphia Phillies

Kyle Schwarber returned to the Phillies after signing a new contract in free agency. | Jayne Kamin-Oncea-Imagn Images

So far this offseason, the Phillies have missed out on some of the market’s top prizes and brought back some veteran players. Kyle Schwarber and J.T. Realmuto were retained on new contracts, while Adolis Garcia was brought in as a potential replacement for Nick Castellanos, whose days in Philadelphia are likely numbered

The Phillies struck out on Bo Bichette, who spurned them to join their NL East rivals in New York. So, where do they go from here? Well, GM Dave Dombrowski doesn’t seem to think they need to make another move, indicating the team is content with where it’s at. But can it really compete with the Dodgers? It’s hard to argue Philadelphia has improved at all this offseason. The addition of Garcia, coming off one of the worst seasons of his career, is hardly inspiring. Realmuto is 35 and coming off a down year, and Schwarber, though a prolific slugger, is entering his mid-30s and now under contract for another five seasons.

As the Mets continue to make move after move to enhance the roster and contend with the Dodgers, the Phillies have been relatively inactive.

San Diego Padres

The Padres re-signed Michael King in free agency. | Denis Poroy-Imagn Images

It doesn’t feel as if the Padres have improved this offseason. The return of Michael King was important, and Sung Mon Song could prove a nice, versatile addition to the infield. But they also saw a trio of key players leave in Dylan Cease, Robert Suarez and Ryan O’Hearn.

The starting rotation is a cause for concern heading into the new season, and letting Cease walk to join the Blue Jays will be a noticeable loss. There had been some inklings that San Diego could turn to Freddy Peralta as a means of bolstering its starting pitching, but the Mets swooped in and got a trade done with the Brewers on Wednesday night.

In addition to the lack of player personnel moves, the Padres have yet to re-up with a new contract for GM A.J. Preller, and the Seidler family is reportedly exploring a potential sale. All in all, this offseason has been a letdown for Padres fans. The usually aggressive organization has been somewhat complacent this winter, and in doing so they’ve fallen further behind the Dodgers while rivals like the Diamondbacks, who traded for Nolan Arenado, and the Giants, who signed starters Tyler Mahle and Adrian Houser, are gaining ground.

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