During last offseason's Winter Meetings, the Boston Red Sox were in a similar place as they were at the beginning of this offseason — coveting Alex Bregman and top tier starting pitching.
Fast forward to 2026 and Bregman is a Chicago Cub, but the Red Sox have added the starting pitchers they wanted and more. Garrett Crochet, Sonny Gray, Johan Oviedo and Ranger Suárez make for the beginnings of a frightening rotation, and maybe the deepest one in the American League.
Boston would not have been able to stock up on so many arms if its 2024-25 offseason went according to plan. The Red Sox hoped to sign Max Fried during the Winter Meetings, but he was snatched up by their archrival New York Yankees and signed to a record-breaking contract for a lefty, eight years at $218 million.
It was reported that the Red Sox's offer for Fried was seven years, $190 million, which obviously was not enough to get the job done. Losing out on him also made the Yankees' rotation that much more fierce — Fried, Carlos Rodón, Gerrit Cole, Luis Gil and Cam Schlittler aren't an easy group to face. But Boston's rebound has been sweet.
Craig Breslow has turned Red Sox's 2024 whiff on Max Fried into a near-full rotation of quality arms
Despite the massive trade package that the Red Sox shipped to the Chicago White Sox for Crochet, his first year on the team has already made the deal worth it. His body of work in 2025 was well worth the recognition he earned as the Cy Young Award runner up to Tarik Skubal. He posted a 2.59 ERA, a 159 ERA+, a 1.028 WHIP, an MLB-leading 255 strikeouts and 46 walks over 205.1 innings of work. The Red Sox were able to sign him to a six-year, $170 million extension shortly after the 2025 season started, keeping him as their ace for years to come.
Suárez will be a Red Sox for just as long after he signed a five-year, $130 million deal. He's been a consistent No. 2-caliber pitcher in the Phillies' rotation since they converted him to a starter in 2022. In 2025, he logged a 3.20 ERA, a 1.220 WHIP, 151 strikeouts and 38 walks over 157.1 frames.
Some may see durability issues when examining Suárez's innings counts, but he delivers when it matters. He's clocked a 1.48 ERA and 1.055 WHIP over 42.2 postseason innings in his career. The Red Sox's rotation is also insanely deep, with Brayan Bello, Kutter Crawford, Patrick Sandoval, Kyle Harrison, Payton Tolle, Connelly Early, David Sandlin and even more Triple-A pitchers as rotation options.
Despite being 36, Gray is still an elite strike thrower and he keeps free passes to a minimum. Oviedo is still a bit of a wild card as he's fresh off elbow surgery and he's only pitched a full season once in his career, but he boasts a deceptive four-seamer (.149 BAA in 2025) and elite 98th-percentile extension.
Rather than signing Fried, the Red Sox collected four new starters who's contracts all have the potential to age better than his deal with the Yankees, which runs until his age-38 season. Yet another free agent whiff by Boston definitely stung at the time, but even the most cynical Sox fans can admit that Craig Breslow's recovery has been pretty darn good.