While the Boston Red Sox have, with some notable exceptions, mostly shunned outside free agents in recent years, the club has focused on spending its money elsewhere. The Red Sox have preferred operating in the trade market for their external acquisitions, but internally, they've been quick to lavish homegrown players with lucrative extensions to keep them in the fold beyond the typical six years of team control.
We saw that happen a lot last season, with Garrett Crochet, Kristian Campbell, and Roman Anthony all receiving long-term commitments. In the case of Crochet, Boston needed to act sooner rather than later, with the ace lefty originally set to hit free agency after the 2026 season. For Campbell and Anthony, the Red Sox wasted no time. Both youngsters got eight-year deals, which cover nearly all of their controllable years, plus buy out a couple of free-agent years as well.
Not all of these moves are strokes of genius. Yes, Breslow can pat himself on the back for Crochet and Anthony, but are we sure we want Campbell around long-term? Maybe some patience would've been warranted there.
The Red Sox likely aren't done extending players they view as future building blocks, and in Red Sox insider Chris Cotillo's opinion, Connelly Early and Payton Tolle could be the next two up.
Red Sox could be eyeing more extensions with Connelly Early and Payton Tolle being players to watch
As Cotillo notes, Boston made sure to hold onto the pair of lefties in trade talks this offseason for a reason. Tolle and Early ranked No. 2 and No. 4 in the system, respectively, and both got a taste of big league action last year.
Early, in particular, looked really good with a 2.33 ERA in his brief 19 1/3 inning cup of coffee. He'd go on to make history in the postseason, becoming the first pitcher to start a winner-take-all playoff game within 30 days of making his MLB debut as the Red Sox's starter in Game 3 of the American League Wild Card Series.
Tolle looked rougher with a 6.06 ERA in his 16 1/3 inning stretch, but just as we can't assume that Early is a future Cy Young winner based on some very small sample dominance, it's way too early to write of Tolle as well.
Despite having a loaded rotation, the Red Sox may want to work these two in at some point in 2026. Injuries are a fact of life, so even with more than five starting quality arms ahead of them in the pecking order, they might still be needed eventually.
So why does Cotillo believe these two could be next in line? It has to do with Craig Breslow's comments.
“We’re always thinking about trying to identify those cornerstone pieces and preserve them for as long as possible,” Breslow said. “We’ll see if anything is able to get over the line but it’s always something that’s part of our strategy for building a sustainable, winning organization.”
Sustainability — that's a good way to put it. If we've learned anything in recent years, it's that starting pitching is the most expensive commodity to acquire. Free-agent starters are getting record contracts every year, and starters with control remaining, even mediocre ones, are fetching insane prospect packages.
By striking while the iron is hot, Boston can keep the cost down on the future of its rotation. Crochet and Ranger Suárez are here for the long haul, but at a combined $54.33 million AAV, how much more the club can actually spend on starting pitching is an unknown once the other pieces start moving on.
Having two promising young hurlers on team-friendly deals waiting in the wings alleviates that concern. So either or both are good bets to get locked up. It would be a gamble, but one that is certainly worth taking.