Red Sox Have to Avoid Long-Term Extensions For Two Young Standouts

It's the only way to proceed...

Mar 18, 2026; Tampa, Florida, USA; Boston Red Sox starting pitcher Connelly Early (71) throws a pitch against the New York Yankees in the second inning during spring training at George M. Steinbrenner Field. Mandatory Credit: Nathan Ray Seebeck-Imagn Images | Nathan Ray Seebeck-Imagn Images

Extensions are all the rage in Major League Baseball these days, but the Boston Red Sox are conspicuously staying away from them this year.

Having completed a barrage of extensions within the last few seasons for the likes of Garrett Crochet, Roman Anthony, and Kristian Campbell, the Red Sox still had a boatload of promising young players this spring without extensions. Some are smartly being avoided, even if it's not by design.

In particular, the urge to extend young left-handed starting pitchers Connelly Early and Payton Tolle should be avoided, if that urge even exists for Boston's front office in any capacity.

If you like our content, choose Sports Illustrated as a preferred source on Google.

Why Red Sox can't extend Early/Tolle right now

Sep 24, 2025; Toronto, Ontario, CAN; Boston Red Sox relief pitcher Payton Tolle (70) delivers a pitch against the Toronto Blue Jays in the ninth inning at Rogers Centre. Mandatory Credit: Dan Hamilton-Imagn Images | Dan Hamilton-Imagn Images

While not alike in all regards, Tolle and Early both have a lot to prove before the Red Sox could even consider extending them. And if the Red Sox are categorically against these particular extensions, it is likely because of the astronomical injury risk young pitchers are facing at the moment.

We saw what could have been a cautionary tale this week with Cade Horton, the Chicago Cubs' excellent young right-hander who finished as last year's runner-up in the Rookie of the Year race. Horton went down for the season with a torn UCL that will require internal brace surgery, and just like that, his age-24 season is gone and his age-25 season will likely be at least interrupted.

Of course, Horton should bounce back physically from the surgery, but if something similar were to happen to Tolle or Early, there would be no guarantee that after that year was missed, the production would be where a team would expect it to be for a pitcher making, say, $10-15 million per year.

Tolle and Early have immense upside, with the latter a bit more proven at the moment, but neither is close to the commodity that Crochet was when the Red Sox brokered his extension. Both reported that they hadn't been approached by the team about extensions during spring training, and it should remain that way for the time being.