Red Sox Draft Strategy Opens Up Possibility For Shocking Move

The Boston Red Sox just put the finishing touches on an interesting 2025 MLB Draft.

Boston’s focus throughout the two-day event was rather obvious, as the organization almost exclusively selected collegiate pitchers. Kyson Witherspoon (Oklahoma; No. 15), Marcus Phillips (Tennessee; No. 33) and Anthony Eyanson (LSU; No. 87) highlighted the group of 15, being joined by just six position players who represented both the college and high school ranks.

Red Sox chief baseball officer Craig Breslow has made a point of replenishing the pitching depth in the upper portion of his farm system over the last two years, doing so by taking arms who are expected to move up rather quickly.

Why?

I found myself asking that question during the draft, understanding the general idea of the approach, but wondering if there was a deeper meaning behind it. The Red Sox have to have some sort of plan that is influencing their recent stretch of business.

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Payton Tolle, for instance, could factor in here pretty soon…

Tolle, for the uninitiated, will soon become the organization’s top prospect after beginning his professional career by procuring a 1.93 ERA across a trio of starts with Double-A Portland. Sox Prospects’ Ian Cundall has already floated that there’s room for another promotion to be made in the coming weeks.

I’d also be willing to bet the same thing… but not to Triple-A Worcester, rather Boston.

Chris Sale and Garrett Crochet, the organization’s two most recent dominant left-handed starters, started their careers the same way with the Chicago White Sox — both debuting as relievers within a few months of being drafted.

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Sale made his first 79 appearances out of the bullpen between 2010 and 2011, before eventually rattling off seven consecutive All-Star appearances as a starter for Chicago and Boston. Crochet made his first 72 appearances out of the bullpen between 2020 and 2023, before eventually rattling off two consecutive All-Star appearances as a starter for Chicago and Boston.

Tolle could follow a similar path, though he’d be cutting out the years of toiling away with a directionless franchise and could instead make an impact for a postseason contender. Boston needs an impact arm in the bullpen, and now has plenty of depth to replace their soon-to-be-top prospect should he get the call.

Whad’ya think? Let us know in the comments if you think Tolle could soon be on his way to Boston.

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