The aftermath of the Boston Red Sox's Wild Card elimination has turned the focus towards what moves the team should make to retool its roster. With trade rumors already swirling out the wazoo, the temptation to package young players for immediate upgrades is strong. That's the true force that young padawans like Chief Baseball Officer Craig Breslow can't resist.
But while some prospects should definitely be dealt to address areas of need, two names absolutely must stay put: left-handers Connelly Early and Payton Tolle.
Red Sox Can't Trade Connelly Early, Payton Tolle Despite Mounting Pressure to Compete
Early, who emerged as one of Boston's most dependable minor league arms in 2024 and 2025, has become a fan favorite and a very promising pitcher within only five starts (including Game 3 of the Wild Card Series against the Yankees).
He offers something the Red Sox can't afford to sacrifice: stability from that left side of the pitcher's mound. In a farm system flush with position players, quality pitching depth remains scarce. Early has shown the ability to mix command with durability, traits that suggest he can become a potential third or second starter. His ceiling wasn't flashy in the beginning, but he proved the doubters wrong by striking out six Yankees in Game 3, which came nearly one month after tallying a record-tying 11 strikeouts in his debut.
Trading Early now, just as he's reached the big-league level, would be very short-sighted. This applies to Tolle, too.
Tolle represents the type of upside the Red Sox desperately need to hang onto. Acquired with expectations of originally developing into a reliever with a hefty fastball, he's changed that thinking into one of the most promising and highest-rising pitchers since Paul Skenes.
He has already flashed swing-and-miss stuff and a bulldog mentality on the mound. His big frame and deceptive delivery make him a nightmare for hitters, and Boston hasn't had many left-handed starts with that kind of profile in recent memory, besides Garrett Crochet. With him, they make a dynamic duo and one to be feared.
Tolle had struggled in the rotation this year and will need to add another pitch to his arsenal, but remember: This was his first season as a pro, and he still made it to Boston before September. That's amazing, and there's no doubt in my mind that pitching coach Andrew Bailey will shape him up before the 2026 season starts.
Red Sox Can't Sacrifice Future
Beyond the on-field value between these two pitchers, there's also an organizational philosophy at play. Boston has struggled in recent seasons to develop and retain homegrown pitching talent. Sending out Early or Tolle would only continue that cycle.
Instead, the Red Sox should focus on clearing logjams among their position players, such as outfield prospects and middle infield depth, to acquire pitching help externally. By holding onto Early and Tolle, they keep a cost-controlled foundation in place while supplementing around it, and that's just good business.
The Red Sox will no doubt be aggressive this winter. They have to be. Fans should expect some trades and perhaps even a splash signing (whether that's just with Alex Bregman in a re-signing is to be determined). Regardless of how tempting some changes might be, Boston must resist the urge to treat all prospects as expendable.
Early and Tolle are the types of pitchers who can stabilize a staff, grow with the core they're assembling, and keep the window of contention open even longer. For once, the Red Sox need to draw a line, and these two should be deemed untouchable to opposing general managers in negotiations.