PHOENIX, AZ: Payton Tolle of the Boston Red Sox pitches against the Arizona Diamondbacks at Chase Field on Sept. 5, 2025. (Photo by Chris Coduto/Getty Images)
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Payton Tolle is generally regarded as the Boston Red Sox’s top prospect in 2026.
The 6-foot-6, 250-pounder pitched across four levels in his first pro season, culminating in a short relief appearance in the American League Wild Card Series. He got the call in the toughest situation possible – the bases loaded at Yankee Stadium in a one-run game. He got Trent Grisham to ground out to second base.
"He’s one of the best left-handed pitching prospects in baseball," prospect expert Ian Cundall of Baseball America told NBC Sports Boston this winter. "I understand that his (2025) season didn’t end how people wanted, but you've got to remember, this is a guy who made his pro debut last year and made it to the big leagues in his first season. That's pretty crazy when you think of it that way.
"I'd expect him to take a really big step forward. We saw how much he progressed last offseason, and if he can do anything close to that this year, watch out. That's a potential mid-rotation-to-better pitching prospect right there."
ARLINGTON, TX: Payton Tolle hits the ball during the 2024 Phillips 66 Big 12 Baseball Championship game between TCU and West Virginia on May 21, 2024, at Globe Life Field in Arlington, TX. (Photo by David Buono/Icon Sportswire via Getty Images)
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Tolle was a two-way player at Wichita State for two years, hitting .313 with 16 homers in 97 games and going 13-9 on the mound. He transferred to Texas Christian and still played some outfield, but developed as a pitcher: 7-4, 3.21 ERA, 125 strikeouts in 81 1/3 innings.
The Red Sox took Tolle out of TCU in the second round of the 2024 MLB Draft. He opened his first pro season with High-A Greenville (SC) and advanced to Double-A Portland (ME), Triple-A Worcester (MA) and then Boston. He appeared in seven games, making three starts, late last season for the Red Sox.
He struck out eight Pittsburgh Pirates in his MLB debut.
Tolle (pronounced TOLL-ee) would replace Sonny Gray in the rotation. Gray, 30, acquired from the St. Louis Cardinals in a trade for three minor-leaguers last Nov. 25, left a start Monday with a tight hamstring. He went on the injured list Tuesday.
“I threw that last 3-2 pitch, and I felt a grab in my right hamstring,” Gray told reporters. “It’s something that I have felt before. In the moment, I kind of knew what it was. When something like that happens, you kind of start going, ‘Should I keep trying to pitch? Should I not pitch? Am I going to make this worse? Am I not going to make this worse?’
"You really don’t know what to do. After a warm-up pitch, it was the same feeling. Not a grab, but a tightness after that. It was just there. That was it.”
Gray was on the IL twice in 2022 and again in 2024 with a similar injury.
BOSTON: Kutter Crawford of the Boston Red Sox pitches against the San Francisco Giants at Fenway Park on May 1, 2024. (Photo by Jaiden Tripi/Getty Images)
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The Red Sox entered 2026 the envy of others due to a deep starting rotation. Rookie left-hander Connelly Early (1-0, 2.29 ERA) has been the best performer thus far.
HOUSTON: Ranger Suárez makes his Boston Red Sox debut against the Houston Astros at Daikin Park on March 30, 2026. (Photo by Kenneth Richmond/Getty Images)
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Ranger Suarez (1-1, 3.22 ERA), signed to a five-year, $130 million contract in January has been OK, while Gray (2-1, 4.30 ERA) was good in two of his five starts.
No. 5 man Brayan Bello (1-2, 6.75 ERA) has not pitched like he did the past three seasons. The Red Sox expect more from the 27-year-old right-hander. He totaled 37 wins the past three years and went 11-9 with a 3.35 ERA in 2025.
Ace left-hander Garret Crochet (2-3, 7.88 ERA) worked six scoreless innings in the season opener. The 26-year-old has been pounded for 27 hits and 10.50 ERA over his last 18 innings in four starts. He has a long way to go to match his 18-5 record, 2.59 ERA and AL-leading 255 strikeouts of 2025.
A year ago, Boston dealt Quinn Priester to the Milwaukee Brewers and regretted it. So they beefed up the pitching corps this off-season. If Gray comes back healthy and Crochet returns to form, all should be fine on the mound for Boston.
In addition to Early and Tolle, the Red Sox have yet another promising left-hander in Jack Bennett. Acquired from the Washington Nationals in December, the 25-year-old has a 2-21 record and 0.55 ERA at Worcester. He’s also 6-6 and relies on an outstanding changeup. MLB.com rates him as Boston’s No. 7 prospect.
Tolle, having been called up previously, probably will be the choice over Bennett. Both could prove quite valuable for the Boston Red Sox for the rest of the 2026 season and beyond.
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