2) The Red Sox have no excuse to let Jordan Montgomery sign anywhere else
The Boston Red Sox have an argument as the top Montgomery suitor because of the sheer number of reasons why it makes sense. Let's start with the fact that the Red Sox need starting pitching. Their rotation was bad in 2023, and swapping Chris Sale for Lucas Giolito might make it worse. Sure, Giolito is more likely to take the ball, but how productive is 32 starts from a guy whose ERA could hover around 5.00 for a third straight year?
Montgomery gives the same durability Giolito provides while also being an all-star caliber arm when he takes the ball. The Red Sox have a potent offense, so they don't need Montgomery to throw no-hitters every time he takes the mound. They just need him to deliver quality starts, which he's more than capable of providing.
What makes Montgomery such an intriguing target for Boston is the fact that he's literally in their backyard. Montgomery is spending his offseason in Boston while his wife starts her residency in the city. Chances are, if the money is right, he'd jump at the opportunity to stay there.
Additionally, Montgomery would have extra motivation to pitch against the Yankees after what transpired a couple of seasons ago. He can become a hero in Boston if he pitches well against the Bronx Bombers.
The lone deterrent here is the money. The Red Sox have been hesitant to spend all offseason. Who knows if they're going to ever show a willingness to spend, but if they were, Montgomery would be the guy to spend on. There is no real reason why the Red Sox, a big market team, should let a legitimate frontline starter who happens to be spending the offseason in their city sign anywhere else, yet that still feels like the likely outcome.