Swift and smart pivots led to productive December for Red Sox

The starting rotation was a priority for the Red Sox this winter, and while Boston didn’t get the No. 1 target on its wish list, it’s been a good couple of weeks for the club on the pitching front.

The Red Sox had their sights set on Max Fried earlier this offseason, but the left-hander ultimately signed an eight-year, $218 million deal with the rival Yankees, forcing Boston to pivot.

The Sox did just that, sending a four-player package led by Kyle Teel to the White Sox for Garrett Crochet, who is under club control for two more seasons before he reaches free agency. Boston remained in the market for another starter, with Seattle’s Luis Castillo among its targets, but according to sources, the Mariners wanted Triston Casas back in a trade, something the Red Sox were unwilling to do unless Seattle took back Masataka Yoshida, who has three years and $55.8 million remaining on his contract.

Once it became clear that a Castillo deal wasn’t going to happen, the Red Sox turned back to the free-agent market, inking Walker Buehler to a one-year, $21.05 million deal that includes another $2.5 million in incentives.

“If Buehler can stay healthy, he might be the best sign of the winter,” a National League executive said. “He can dominate when he’s right. Plus they didn’t have to give up a pick to sign him.”

Not only did the Red Sox not have to give up a pick for Buehler, but if he has a solid season, they might be able to add a pick next winter if they extend him a qualifying offer.

Boston also signed Patrick Sandoval for two years and $18.25 million, adding more depth to an already deep rotation.

“I like the pivot and would argue that the total cost is less significant than Fried and Castillo,” an American League executive said. “[Buehler] is a pricey gamble, but if they think that they are better at pitching development than the Dodgers, it makes sense.”

Adding Buehler and Crochet to the top of the rotation gives the Red Sox a strong group for 2025, with some combination of Tanner Houck, Kutter Crawford, Brayan Bello, Lucas Giolito and Garrett Whitlock filling out the rest of the starting staff. Sandoval, who is rehabbing from last June’s Tommy John surgery, could be an option during the second half of the season.

“Crochet is a good get,” an NL executive said. “They have $41 million invested in Buehler and Giolito, both of whom are lottery tickets.”

Buehler’s contract is for the same value as this year’s qualifying offer, which the Dodgers opted not to extend to him after the season. One NL executive was “pretty shocked” that Buehler landed that salary, though the one-year term is relatively low risk for a big-market club such as the Red Sox.

“That’s the type of relatively low-risk/high-upside signing a club with financial resources should be making,” an NL executive said. “It gives them another playoff-caliber starter without risk to their future payroll.”

All quiet on the free-agent front?

Several of this year’s top free agents have already found homes, with Fried, Juan Soto, Blake Snell and Willy Adames all signing nine-figure contracts during the past month. But a number of big names remain available, with Corbin Burnes, Alex Bregman and Pete Alonso leading that group.

Christmas week is typically a quiet time in free agency, but with so many notable players still looking for deals, could this year be different?

Houston had always been considered a fallback option for Bregman, who was sitting on a six-year, $156 million offer on the table from his long-time club. But the Astros’ trade for Isaac Paredes and the signing of Christian Walker appear to have slammed the door on a return to Houston, leaving Bregman in search of a new team.

The Tigers remain interested in the third baseman, sources said, but it is unclear whether Detroit will be willing to give Bregman the type of deal he is seeking. The Red Sox remain interested as well, though Bregman would have to move to second base to go to Boston unless the Sox made another move by trading Casas, which would allow them to move Rafael Devers across the diamond to first base.

Casas is one of the more intriguing trade options for clubs looking to address first base, especially now that the free-agent market at the position has thinned considerably. With Walker, Paul Goldschmidt (Yankees) and Carlos Santana (Guardians) off the board, Alonso is the only significant name out there, though few teams are expected to pay the slugger what he wants. Multiple executives believe an Alonso/Mets reunion is inevitable, albeit on a deal with one or two opt-outs, enabling him to test the market again in a year or two if he so chooses.

As for Burnes, who entered the offseason as the best free-agent starting pitcher, the Giants and Blue Jays have been considered his two most likely landing spots. San Francisco has had an offer on the table, but sources have indicated that the Giants may be getting impatient, prompting them to consider other ways to improve the club via free agency.

Even after extending Matt Chapman and signing Adames, the Giants could look to add another bat, with Alonso, Anthony Santander, Jurickson Profar and Teoscar Hernández among the potential options.

According to sources, Burnes is seeking a deal worth at least $245 million, which would match the seven-year, $245 million deal Stephen Strasburg signed in December 2019 as the third-highest guaranteed contract in history for a starting pitcher.