4. Jordan Montgomery - Arizona Diamondbacks
The 2024 season was an absolute disaster for Arizona Diamondbacks pitcher Jordan Montgomery. From not being signed until the regular season was about to begin, firing his agent Scott Boras, suffering an injury early in the year, to the owner of the Diamondbacks publicly stating his regret of singing Montgomery, this is clearly someone who could use a change of scenery. With the expectation that the Diamondbacks will eat a significant chunk of his salary just to get him out of Arizona, the Guardians should definitely inquire about potentially acquiring him.
While the relatively low amount of money the Guardians would have to pay Montgomery should they trade for him is definitely a large factor, holding some belief that 2024 is an anomaly and not an accurate portrayal of who he is as a pitcher. To be blunt, 2024 was a mess for Montgomery, and his 6.23 ERA, 1.650 WHIP, and 6.4 strikeouts per nine innings are not necessarily a surprise.
Betting on a bounceback year for Montgomery is risky, but at the same time, it seems somewhat likely to happen, especially if he gets out of Arizona. Most of Montgomery's struggles came while pitching in the hitter-friendly environment that is Chase Field. There is no guarantee he will return to his sub-4.00 ERA form, but it seems a lot more likelier than seeing a repeat of 2024 in 2025.
What it all comes down to is trying to find a match that works between team and player. Right now, Montgomery and his current contract situation seem like an ideal trade target for a Guardians team desperately in need of starting pitching.