The Red Sox Must Risk Big Contracts to Win Big—Time for John Henry to Step Up

The Boston Red Sox made a statement last week, securing left-handed starter Garrett Crochet from the Chicago White Sox in a blockbuster trade. In exchange, the Sox parted with a quartet of prospects, strengthening their rotation for at least the next two seasons. This trade is a win for Boston, but if they truly want to position themselves for sustained success, their offseason work is far from over.

The Red Sox must now turn their attention to two critical moves: signing another top-tier starter and locking up Garrett Crochet to a long-term extension.

Garrett Crochet: The New Face of the Rotation

Crochet’s arrival in Boston is already being hailed as a game-changer. Last season, the 24-year-old posted a solid 3.58 ERA in 32 starts for the White Sox, a notable achievement for a pitcher in his first season as a full-time starter. With a mid-to-high 90s fastball and a sharp slider, Crochet has the tools to become a cornerstone in Boston’s rotation.

Even more promising? The young lefty is reportedly open to signing an extension with his new team. As MassLive’s Sean McAdam pointed out on the day of the trade, sources familiar with Crochet’s thinking say he’s eager for stability, and the Red Sox have a real chance to secure his future in Boston beyond 2025.

In an ideal world, the Red Sox would get this extension done sooner rather than later, locking Crochet in as a long-term piece of their pitching puzzle. His potential for growth is massive, and if he continues his trajectory, he could be one of the most reliable and dynamic arms in the league.

Time to Sign Another Top Starter

But Boston’s work isn’t done. While Crochet’s addition bolsters the rotation, the Red Sox need to make another splash in the starting pitcher market to truly compete in the American League. The offseason has brought a variety of talented arms to the forefront, and one name that stands out is former Cy Young winner Corbin Burnes.

Burnes, who has been a stalwart in the Brewers’ rotation for several years, posted a 2.92 ERA, 1.096 WHIP, and 8.4 strikeouts per nine innings last season. The 30-year-old is entering the prime of his career and is likely looking for a contract well over $250 million. While that kind of commitment is risky, especially considering the Red Sox’s previous experiences with long-term pitching contracts (think Chris Sale and David Price), the risk could be worth it.

Boston’s window to win is opening, and Burnes would immediately provide an ace-caliber arm to the front of the rotation. Alongside Garrett Crochet, Lucas Giolito, Tanner Houck, and Brayan Bello, Burnes would give the Red Sox one of the most potent rotations in baseball, one capable of carrying them deep into the postseason in 2025 and beyond.

The Elephant in the Room: John Henry’s Reluctance to Spend

The biggest obstacle standing in the way of these moves, however, is Red Sox owner John Henry. After the failures of the Chris Sale and David Price contracts—both of which became millstones around the team’s neck—Henry has been understandably hesitant to hand out long-term deals to pitchers. The Athletic’s Ken Rosenthal recently reported that Henry is “reluctant to award long-term deals to pitchers,” based on these past burnouts.

While this caution is understandable, it also limits the team’s ability to build a sustainable winner. If the Red Sox want to contend for championships in the coming years, they’ll need to take risks, especially with pitchers who are in their prime or entering it. Offering Burnes a long-term deal or extending Crochet would send a message that the team is serious about building a rotation that can dominate for years to come.

It’s time for Henry and the front office to move on from the fears of the past. The Red Sox need to take the lessons learned from the Sale and Price contracts—not by avoiding long-term investments in pitching, but by being more strategic with them. In the case of Burnes and Crochet, these are high-end, proven pitchers who could make all the difference for Boston’s future.

The Future of the Red Sox

A rotation anchored by Burnes, Crochet, Giolito, Houck, and Bello would not only make the Red Sox a playoff team in 2025 but also position them as a contender for the American League Championship Series (ALCS) and beyond. The offense, led by rising stars and established hitters, would have the pitching support it needs to take the team deep into October.

But that future requires action. The Red Sox have the opportunity to reshape their rotation and secure their place among the AL elite—but only if they are willing to make the moves necessary to lock in long-term stability. This means offering competitive contracts to pitchers like Burnes and extending Crochet before his value soars even higher.

For Red Sox fans, the next few months could define the direction of the franchise for years to come. Let’s hope that John Henry is ready to take the necessary steps and commit to winning at the highest level. The potential for greatness is right there—now it’s time for the Red Sox to make it happen.