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3 pitchers to snag just in case - 1. Blake Snell
After winning the Cy Young Award this season, Blake Snell seems to get little love in free agency. His market will open up once Ohtani and Yamamoto sign, but in the meantime, he appears, at best, to be everybody's 3rd choice. Snell won't be cheap, given the caliber of season he just recorded. In 1.80 frames, he posted a league-best 2.25 ERA while notching 234 strikeouts in the process. Like Montgomery, Snell is a southpaw who is only 30 years old.
Thinking outside the box and adding Snell to a contract that The Athletic (subscription required) estimates will only cost 122M total for five years gives the Cubs another starter at the top of their rotation for almost the same AAV that Marcus Stroman cost. Given Snell's upside, he makes the Cubs better, and the team cannot afford to miss on every top arm again this winter. Snell gives the Cubs two top 5 Cy Young finalists from 2023 and a lethal one-two punch in the rotation.