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The road from Rookie of the Year finalist to Cy Young is short, but Payton Tolle is on it

Kevin McGonigle took home the ROY hardware, but Boston's mustachioed lefty has the stuff to chase a much bigger award.
ByAnthony Ranaudo
Sep 22, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Payton Tolle (70) looks to throw a pitch against the Cleveland Guardians in the first inning at Fenway Park. Mandatory Credit: David Butler II-Imagn Images
Sep 22, 2026; Boston, Massachusetts, USA; Boston Red Sox pitcher Payton Tolle (70) looks to throw a pitch against the Cleveland Guardians in the first inning at Fenway Park. Mandatory Credit: David Butler II-Imagn Images | IMAGN IMAGES via Reuters Connect

Awards week kicked off on Monday night, with the American and National League Rookie of the Year announced. In the AL, Kevin McGonigle triumphed, and deservedly so after he led all AL players with 7.1 bWAR. Still, Red Sox fans knew the third name on the finalist list — Payton Tolle — deserved a lot more love in the conversation than he received.

Tolle won over his clubhouse before he ever threw a regular-season pitch. When Alex Cora wanted to break up the spring training grind, he called on Tolle, who delivered a shirtless American history lesson in jean shorts and cowboy boots, with "USA" shaved into his chest hair. From there, Tolle hugged Seattle's Dominic Canzone while tagging him out, dropped for a push-up after slipping on the mound in Baltimore, and then charmed a national audience as a World Series correspondent.

The personality is what some fans may know him for, but the arm is really special, too. Tolle is a 6-foot-6 lefty who has touched 100 mph, with extension that ranks in the 98th percentile. He's also the type of pitcher who can crack a smile right before doing something near impossible, which is exactly what he did while completing an immaculate inning to open a Sept. 13 start against the Royals.

Payton Tolle's rookie numbers point toward a future Cy Young race for Red Sox

Tolle didn't even make the Opening Day roster, yet he made 26 starts after his April 23 recall and finished with a 3.03 ERA, 1.10 WHIP and 171 strikeouts against 40 walks over 148 2/3 innings, all as a starter. He fell just 13 1/3 innings shy of qualifying, allowed two earned runs or fewer in 17 of those starts, and ranked in the 95th percentile in expected ERA (2.70) and the 96th percentile in chase rate.

It got us thinking, and history shows the jump from ROY ballot to Cy Young can happen fast for elite arms. Dwight Gooden won Rookie of the Year in 1984 and the Cy Young a year later, while Justin Verlander and Jacob deGrom also turned Rookie of the Year trophies into Cy Young hardware. Paul Skenes is the freshest case study, winning NL Rookie of the Year in 2024 while finishing third in Cy Young voting, then capturing the award unanimously in 2025. 

Tolle isn't Skenes, but the gap is smaller than you'd think. As a rookie, Skenes made 23 starts and threw 133 innings with a 1.96 ERA, 170 strikeouts and 32 walks. Tolle made three more starts, covered 15 2/3 more innings and struck out one more batter, while his strikeout rate (10.4 per nine innings to Skenes' 11.5) and walk rate (2.4 to 2.2) sit in the same neighborhood. The ERA gap is real, but the underlying skills aren't far apart.

As a former 6-foot-7 pitcher who came through the Red Sox system myself, I know how rare it is to find a frame that efficiently moves down the mound like that. Tolle's personality will keep him as a fan favorite around the game for years, but what excites me most is watching him grow into an ace (with Garrett Crochet, of course) of this rotation — plus he is looking like a fixture in the Cy Young race, giving Red Sox fans something real to hang their hats on.

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