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Red Sox Top Prospect Payton Tolle Predicted to Skip Triple-A, Take Garrett Crochet, Chris Sale Path

Jul 18, 2025 3:00 PM EDT

Just how creative are the Boston Red Sox willing to get heading into the trade deadline and after the 2025 MLB draft?

The Red Sox did an excellent job adding multiple high-leverage college arms, which is never a bad idea. Teams always need starting pitching, relief help, and more in a staff.

While the Red Sox rotation had the opportunity to be one of the best in baseball this year and has struggled a bit, there’s reason to believe that in the future, things could go as planned.

One of the players who will help them achieve that is Payton Tolle, a left-hander who has continued to throw the baseball at a very high level over the first year of his professional career.

Tolle didn’t pitch at all in 2024, but he’s posted a 3.25 ERA in 2025, including a 1.93 ERA in two starts in Double-A.

When considering the potential implications of the Red Sox’s draft decisions and how they could impact players like him, NESN recently proposed the idea of him advancing directly from Double-A to the show, skipping Triple-A.

“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,” they wrote.

It’d be surprising to see the Red Sox make this decision, but it obviously can’t be counted out.

As he touched down, Chris Sale and Garrett Crochet did similar things.

To suggest that Tolle will be as good as one of those two arms is unfair given what they’ve done throughout their careers, but the left-hander has above-average stuff, and that plays at the highest level.