The Red Sox are looking to improve their rotation this winter but it remains to be seen how exactly that will play out. They have previously been connected to top free agents such as Corbin Burnes, Max Fried and Blake Snell, as well as trade candidate Garrett Crochet.

This week, Bob Nightengale of USA Today reports that the Sox actually want to of those top free agents. Sean McAdam of MassLive reports that the Sox are continuing to keep tabs on the pitching market while engaging with Juan Soto. They did have some interest in lefty Yusei Kikuchi, though it’s unclear how strong that interest was and he now has an agreement with the Angels. As for Crochet, McAdam reports that the Sox have pulled off the gas a bit there, with some unknown club getting “very aggressive” recently.

Very early in the offseason, chief baseball officer Craig Breslow said the club would be looking to the “raise the ceiling” in the rotation and these pursuits all align with that goal. Burnes, Fried and Snell all have long track records of major league success, with Burnes having a Cy Young award and Snell having two of them. Fried doesn’t have the hardware but does have a 3.07 earned run average in just under 900 career innings. Crochet only just transitioned to the rotation in 2024 but did so with aplomb, posting a 3.58 ERA, 35.1% strikeout rate, 5.5% walk rate and 45.1% ground ball rate in 146 innings.

Any one of those pitchers would be a nice upgrade for Boston or any other club, though that will also make them very popular. In addition to the Sox, those pitchers have been connected to clubs like the Blue Jays, Orioles, Yankees, Dodgers and Padres. There are plenty of other clubs that also make sense, even if they haven’t been explicitly tied to those pitchers in rumors.

For the Sox to come away with two of those pitchers would make for quite an aggressive offseason, but that’s exactly what the club has been signaling. Both Breslow and CEO Sam Kennedy have made comments suggesting the club is planning to act boldly this winter, with Kennedy recently saying that paying the competitive balance tax is on the table. Many fans of the club will bring up last year’s “full throttle” comments from chairman Tom Werner and how those didn’t precede much action last winter, but the club is being more specific this year. Kennedy has repeatedly said the goal is to field a club capable of winning 90 to 95 games and taking the division.

Spending money on free agents is one way they could go about accomplishing that. RosterResource projects the 2025 club for a payroll of $138MM, well below their $184MM spending from 2024, which was itself a drop from what they spent in the previous decade. RR pegs the club’s CBT number at $171MM, which is $70MM below the lowest threshold.

There’s plenty of room in there for two notable contracts, though successfully signing Soto would obviously completely change the calculus, given the expectation that he’ll sign a record-setting contract. Leaving that aside for now, big contracts for two of the big free agent starters is a feasible outcome. As part of MLBTR’s Top 50 Free Agents post, each of Burnes, Fried and Snell were projected for contracts with average annual values between $26MM and $32MM. Putting two of those onto Boston’s payroll still wouldn’t even get them to the CBT line. They will presumably also make additions to the bullpen and maybe the position player group as well, but with a willingness to cross the line, all sorts of possibilities could be on the table for them.

Crochet would be far cheaper from a financial perspective, with the biggest cost coming in the form of prospect capital. Since he has spent so much of his career either working in relief or injured, he is down to two years of club control but hasn’t been able to raise his salary very high through the arbitration process. He made just $800K in 2024 and MLBTR contributor Matt Swartz projects him for a raise to just $2.9MM in 2025. He would be due another raise in 2026 before he’s slated to become a free agent.

Two years of an ace-caliber pitcher for that kind of money is tremendous value, which is why Crochet figures to be very popular in trade talks. The Red Sox have a strong farm system and could certainly get a deal done if they wanted to, though it seems some mystery club has pulled ahead of them, per McAdam’s reporting.

For now, the Boston rotation projects to be fronted by Tanner Houck, Brayan Bello and Kutter Crawford. Houck had a breakout season in 2024 but may have run out of gas, as he had a 2.54 ERA in the first half and a 4.23 mark in the second. Bello and Crawford are each coming off decent but not outstanding seasons, each finishing with an ERA in the 4.35-4.50 range. Lucas Giolito and Garrett Whitlock could be in the mix in 2025 but they are fairly unknown quantities right now as each underwent internal brace surgery in 2024.

Adding to that group would improve Boston’s chances in 2025 while bumping guys like Cooper Criswell, Richard Fitts and Quinn Priester to depth roles, either in the minors or in the big league bullpen.

The interest in Kikuchi suggests that the Sox are also open to some of mid-market options. With Kikuchi now gone, some of the other names that could be in line for somewhat similar deals include Jack Flaherty, Sean Manaea, Nathan Eovaldi, Luis Severino and old friend Nick Pivetta.

The qualifying offer will likely be a factor, depending on who the Sox ultimately sign. Snell, Eovaldi and Flaherty were ineligible to receive a QO, Snell and Eovaldi because they had already received one and Flaherty because he was traded midseason. Burnes, Fried, Manaea and Severino rejected QOs, meaning the Sox would have to forfeit their second-best pick in next year’s draft and $500K of international bonus pool space to sign them. Pivetta rejected a QO from the Red Sox, meaning they stand to receive a compensation pick just ahead of the third round if he signs elsewhere, though they would not receive that pick if they ultimately re-sign him.