2, Blake Snell
It's not too often that a pitcher hits the open market immediately after winning a Cy Young award, so Boston needs to make the most of this opportunity and sign Blake Snell ASAP.
Snell was fantastic in 2023, going 14-9 for the San Diego Padres while leading the majors with a 2.25 ERA. He also racked up 234 strikeouts in 180 innings while posting MLB's lowest hit rate (5.8 H/9).
Snell's control problems are a bit of a concern (he led the majors in walks this season), but they haven't stopped him from being one of the most dominant pitchers in baseball. The 30-year-old lefty already has a pair of Cy Young awards under his belt, including one with the Tampa Bay Rays in 2018.
Similar to Montgomery, Snell is familiar with the AL East after spending the first five years of his career with the Rays. He also has a solid postseason track record, going 4-3 with a 3.33 ERA and 61 strikeouts in 48 2/3 playoff innings so far.
Given his inconsistency, injury history and incredible upside, Snell is the ultimate high-risk, high-reward signing. A big-market team like Boston can afford to roll the dice on Snell. If he doesn't work out, we can afford to take the hit. If he does, we'll reap the rewards.