Jordan Montgomery
Finally, we come to Jordan Montgomery who should absolutely be near the top of the Red Sox's wish list this offseason. Among the free agent starting pitchers this offseason, no pitcher helped their stock more in 2023 than Montgomery as he is now positioned as one of the top arms available period after being perennially under-appreciated in his career.
Aside from the fact that all the guy does is post at least a low 3 ERA each season while throwing a ton of strikes every year since 2020, Montgomery has a lot going for him. His fastball grades out well despite the fact that he doesn't throwing particularly hard which should appeal to Boston's new front office, he is coming off a career best season where he was an integral part of the Rangers' run to a World Series title, and he doesn't have a qualifying offer attached to him as he wasn't eligible to receive one at the end of the season.
While the secret is out on Montgomery now and most of the league is trying to convince him to join their ranks, Boston does have some advantages in the chase to acquire him. Not only do the Red Sox have a ton of young talent coming up from the minors which points to a bright future for the team, but Montgomery is already living in the Boston area as his wife dermatology career has fortuitously brought them nearby. Monty isn't going to leave a bunch of money on the table just because of that, but it does seem to be a point in Boston's favor.