Blake Snell
Just like Montgomery, Blake Snell is somehow still on the open market in March. The reasons are a little different, but it's still not good for baseball that two of the top 10 pitchers entering free agency are still without a team with Opening Day just a few weeks away.
Like Montgomery, Snell is the answer at the top of the rotation for the Red Sox, bringing a Cy Young award in both leagues and two ERA titles to the table. Snell is also a lefty, so he would bring a different flair to an all-righty rotation in Boston.
The concerns for Snell are clearer than Montgomery's, the most glaring being his lack of durability. 2023 was the first year Snell made more than 30 starts since 2018, with the common denominator also being the Cy Youngs and ERA titles. He also rarely goes farther than five or six innings into a game, which doesn't help reset a bullpen either.
The fact that Snell has only two seasons of 30 starts and that he doesn't go deep into games are red flags for sure. However, the Red Sox shouldn't pass up a two-time Cy Young winner who has a lot of the skills that they need in the rotation right now.