After nearly two decades of being unable to develop homegrown pitching, the Boston Red Sox, under Chief Baseball Officer Craig Breslow have become somewhat of a pitching factory. Under Breslow, Boston has developed Connelly Early, Jake Bennett, Anthony Eyanson, and the crown jewel of the new pitching pipeline, Payton Tolle, who has established himself as one of the best young arms in the game. 

Along with developing pitching at a much higher rate, the organization has made a philosophical shift, pushing to extend its young core pieces well before they’re set to reach free agency. Among the players already locked into long-term deals are outfielders Ceddanne Rafaela, Roman Anthony and Kristian Campbell, and pitcher Brayan Bello. Next on the docket for Breslow and the Boston front office should be locking up Tolle as the future ace of the team. 

In 27 career starts, the 23-year-old has posted a 3.48 ERA, holding opponents to a .223 batting average and striking out 10.4 batters per nine innings. While his numbers are already impressive on their own, they’re much more impressive considering they are hampered by a 7.35 ERA in his first three career starts in 2025. In 2026, Tolle has seen much better results, posting a 3.15 ERA in 137 innings pitched across 24 starts, while ranking in the top 10 among all qualified rookie starters in ERA (3.15, 5th), strikeouts per nine innings (10.45, 2nd), walks per nine innings (2.43, 6th) and Fangraphs wins above replacement (3.7, 2nd). 

Not only is Tolle one of the best young starters in baseball, but he is quickly establishing himself as one of the best starters in the sport, period. Tolle ranks in the 90th percentile or better among all starters in expected ERA (2.68, 95th percentile), expected batting average (.198, 92nd percentile) and chase rate (36.2 percent, 95th percentile). His strikeout rate of 28.9 percent falls in the 89th percentile. By nearly every metric, Tolle is a frontline ace in the making. 

Of the eight rookie starters to throw at least 70 innings in a single season for the Red Sox since 2000, Tolle leads the pack in fWAR (3.7), ERA (3.15), strikeouts per nine innings (10.45) and opponent batting average (.218), while trailing only Bennett in walks per nine innings and WHIP. 

Throughout his rookie campaign, Tolle has made franchise history on multiple occasions, including becoming the second pitcher in Red Sox history to strike out 12 or more batters while walking zero at the age of 23 or younger, joining Roger Clemens, who accomplished the feat twice. In his most recent start, a six-inning, 12-strikeout performance on Sunday in Baltimore, Tolle became the first Boston starter under 24 years old to make three starts with 11 or more strikeouts in a single season since Clemens in 1986.

While some players, like first baseman Triston Casas, are approached by teams about an extension, they choose to bet on themselves, spurring any talks to lock in guaranteed money regardless of how their careers may play out. Others choose to lock in a set amount of money and protect themselves from any of the variables that go into being a successful big leaguer, while still setting themselves up for a major payday at the end of their first deals. 

The 23-year-old has been asked several times about a potential deal to keep him in Boston long-term, and he certainly appears to fall into the latter category. Tolle told Alex Speier of the Boston Globe on Aug. 18 that he would “for sure” be open to those discussions. “We’re calling Boston home right now for however long they want me to call it home,” he continued. He did note, though, that the team and his agent had not discussed the possibility as of yet. 

Tolle was again asked about a potential deal on Sept. 2 when appearing on WEEI’s ‘Jones and Keefe’ Show, reiterating that he and his wife will call Boston home for however long the team wants them to, but that those conversations have not taken place. 

While the conversations between the two sides haven’t begun, it would be in Breslow and the Red Sox’ best interest to begin the discussions as soon as possible, because the price is only going up as Tolle continues to establish himself as a future ace. 

The Red Sox will look to extend their winning streak to six and clinch a series win over the Los Angeles Angels on Tuesday night in game two of a three-game set from Fenway Park. Patrick Sandoval (1-4, 4.41 ERA) will get the start for Boston opposite Reid Detmers (4-8, 3.44 ERA) for Los Angeles. First pitch is set for 6:45 p.m. ET.