If the Boston Red Sox were to start locking up more of their young players, one of them would have to be left-hander Payton Tolle.
The 22-year-old pitcher was drafted out of TCU in the second round by the Red Sox in 2024, and he accelerated through the farm system. He started in High-A, where he rose all the way up to the MLB roster in just 20 games, starting 18 of them and posting a 3.04 ERA while striking out 133 batters in 91 2/3 innings pitched. He made his major league debut and famously struck out eight batters in 5 1/3 innings. He was moved to the bullpen after giving up seven runs in just five innings pitched.
To start this season, he was in Triple-A Worcester to work on his new curveball and refine his arsenal. After posting a 3.00 ERA with 19 strikeouts in 15 innings pitched, Tolle looked like a new and improved player. He was recalled to the Red Sox on April 23, and he never set foot in the minors again.
He's struck out 159 batters (11th in baseball) with a 3.15 ERA in 131 innings pitched. He's also walked only 37 batters with a 10.4 K/9, which is the highest on the team. He can become the future of the Red Sox.
When should the Red Sox extend Payton Tolle?
The opportunity to get Tolle extended was in August. Whether or not CBO Craig Breslow wants to pull the trigger, he has until December 1st to do so, with the league's CBA expiring then and a possible lockout occurring.
As of now, neither Tolle, his agent, nor the Red Sox have discussed a possible extension yet. Tolle has been adamant about valuing his time in Boston for as long as possible. "We're calling Boston home right now for however long they want me to call it home" (h/t Alex Speier of the Boston Globe).
The best time to approach the 23-year-old left-hander is in 2027, preferably around the start of the season. If there is a season in 2027, Breslow needs to approach Tolle, alongside Wilyer Abreu and possibly Jake Bennett, about an extension. There won't be much wiggle room with negotiations afterwards, and they'll demand much more money than Red Sox ownership would be comfortable parting with.
In a more positive twist, there's still plenty of time to do so. Tolle is very young, and he'll be the future one-two-three punch with Garrett Crochet and Ranger Suárez in the rotation. Depending on how long he'll stay, the window for contention has only just begun. Let's see what it'll entail.
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