Payton Tolle is in line to put his name in some very old Red Sox company.
If Boston hands the ball to the rookie left-hander in Game 1 or Game 2 of its playoff series, he would become the youngest pitcher to start one of the first two games of a postseason series for the Red Sox since Babe Ruth did it in the 1918 World Series. According to former Red Sox director of baseball communications and media relations JP Long, that would make Tolle the youngest Boston starter in that spot in more than a century.
At 23 years old, Tolle has forced his way into the conversation. Rob Bradford of WEEI reported Saturday that Tolle has a “good shot” to get the Game 1 nod, a possibility that would have sounded far-fetched only a few months ago. Boston’s top three starters right now are Tolle, Sonny Gray and Ranger Suárez, and the club is very likely to run into the New York Yankees in the first round.
That matchup matters. Tolle has had success against Boston’s biggest rival this season, and the Yankees have had issues against left-handed pitching.
That gives the rookie a real case for the opening assignment. Gray has been Boston’s ace all year, while Suárez brings postseason experience and also throws left-handed.
On paper, the Red Sox can justify any of the three.
Tolle’s season has already turned into one of the more striking stories on the roster. He owns a 3.02 ERA with a 166-to-38 strikeout-to-walk ratio over 143 innings. He also didn’t break camp with the Red Sox, instead getting promoted on April 23 before taking off from there.
The rise has been fast enough that Tolle should draw votes in the American League Rookie of the Year race, even if Kevin McGonigle is widely expected to win the award.
However Boston lines up its rotation, Tolle’s case stands out for one simple reason: if he gets the call in Game 1 or Game 2, it won’t just be a normal playoff start. It would be history.
In Other News...
Payton Tolle Just Gave Red Sox Fans Another Reason To Love Him
Payton Tolle had more than the usual rookie celebration in his pocket when the Red Sox wrapped up their postseason spot. The left-hander spent part of the clinch festivities speaking with reporters, and he came off as a pitcher who not only knows how far he has come since 2025, but also understands why Bostons run matters so much right now. His 2026 season has turned into a strong one, with a 9-6 record, a 3.02 ERA and 166 strikeouts across 25 starts.
For a club already looking ahead to October, Tolles growth has become another reason the fan base has taken to him so quickly. He did not sound like someone content to simply enjoy the moment, either, as he expressed optimism about the Red Soxs playoff chances and the kind of baseball this group can still play. For a team built around believing the next step is still possible, that kind of confidence from a young arm only adds to the intrigue. [Read more 🡒]
Red Sox Could Soon Face A Tough Garrett Whitlock Decision
Garrett Whitlocks future keeps circling back to the same question for the Red Sox: is he more valuable as a high-leverage reliever, or could he bring even more to the club if he moves into the starting rotation? Whitlock has the kind of pitch mix that can make the idea tempting, and Boston has long appreciated the versatility he brings to the staff. With his contract situation giving the team options for 2027 and 2028, this is the sort of decision that could shape not just his role, but part of the clubs long-term pitching plan.
The appeal is obvious, but so are the concerns. A move to the rotation would ask more of Whitlock physically, and health has to be part of the conversation whenever Boston weighs changing a pitchers usage pattern. For now, the Red Sox can keep exploring the possibility without rushing into anything, but the fact that the discussion is even on the table suggests this could become one of those strategic calls that defines how the roster is built in the seasons ahead. [Read more 🡒]
Red Sox Suddenly Face A Pre-Playoff Seeding Problem At Fenway
The Red Sox have already punched their ticket to October, but the final three games at Fenway Park suddenly carry a different kind of importance. Boston is set to close the regular season against the Cubs, and a significant storm forecast could put the schedule in flux just as the club is trying to settle into its playoff rhythm.
MLB may be forced into some awkward juggling if the weather knocks games off the board, with postponements and possible makeup plans creating the kind of late-week uncertainty teams prefer to avoid. Doubleheaders could enter the conversation, and so could the impact on rest before the postseason begins, leaving Boston with one more variable to manage before the real games start. [Read more 🡒]