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It would seem likely that the Houston Astros will prioritize upgrades for their starting rotation this offseason, especially with the likelihood that Framber Valdez will be pitching elsewhere next season. That said, the Astros can't avoid the fact that their team broke during the final month of the regular season. With that in mind, in looking for offensive help, the Astros could turn to a team they love to hate.
New York Yankees outfielder Trent Grisham is set to become a free agent this offseason, and while he will likely have a qualifying offer attached to his profile, Grisham figures to be coveted this winter.
The 2025 season was a breakout campaign for Grisham, setting a career-high in home runs with 34. In 581 plate appearances, Grisham slashed .235/.348/.464 with a wRC+ of 129. That said, his struggles during the Yankees' playoff run may add to teams being skeptical of giving him a lucrative long-term contract. Especially since 2025 has been the only season of his career where he has had consistent success.
Trent Grisham might join the one team he’s haunted the most
Assuming the Astros will be in the market for offensive improvements this winter, Grisham could make sense. Grisham won't be at the top of the market, such as Kyle Tucker, Kyle Schwarber, or Pete Alonso, and the lack of sustained success likely puts his price right in the range of what the Astros would be willing to pay for an outfielder this season. In other words, like Bleacher Report's Kerry Miller suggests, it would make sense for the Astros to check in on Grisham.
If nothing else, it would ensure that Grisham can no longer haunt the Astros. In 19 games played against the Astros in his career, Grisham is hitting .290 with 7 home runs and 19 RBI. As the old adage goes, if you can't get them out, sign them.
Signing an outfielder like Grisham would fill the dark void that was left field for Houston last season, while ensuring that the aging Jose Altuve stays far away from playing in the outfield again.