The Boston Red Sox on Tuesday, following chief baseball officer Craig Breslow’s promise to acquire a No. 2 starter who is capable starting a playoff game behind Red Sox ace lefty Garrett Crochet, made a significant trade that may â or may not â be designed to do just that.
Breslow traded two pitching prospects â hard-throwing lefty Brandon Clarke and Richard Fitts, who has already made 14 major league starts, for a righty who was once a first-round draft pick â in 2011.
Sonny Gray came over in the deal from the St. Louis Cardinals, his fifth team in a 13-year career. At 36 years old, Gray has proven to be one of the most reliable arms in the game, throwing more than 160 innings seven times in his career, and in each of the last three seasons.
Red Sox Rotation Still Needs More
But is Gray the bona fide No. 2 starter that Breslow claimed to be looking for? Breslow isn’t sharing his opinion, instead asserting that, âI donât know how much sense it makes, in November, to put a number on a guy,â as quoted by NESN.com.
One thing is for sure, with three spots in the rotation, including homegrown No. 3 starter Brayan Bello, Breslow still has some work to do to fill the other two startersâ jobs. And according to a prediction published Thursday by MLB analyst Ryan Finkelstein of Just Baseball, he may find one of those starters in the form of a former New York Yankees starter now on the free agent market.
Breslow and his predecessor Chaim Bloom â now president of baseball operations for the Cardinals â have shown a certain fondness for acquiring players who have spent time with the Yankees organization. Red Sox closer Aroldis Chapman pitched seven seasons for the Yankees while setup man Garrett Whitlock was a Rule 5 draft selection from the Yankees farm system.
Michael King Pitched 5 Years in New York
Catcher Carlos Narvaez came over in a trade last offseason from the Yankees, and outfielder Rob Refsnyder, now a free agent himself, was a 2012 Yankees fifth-round pick. Even Fitts was acquired from the Yankees after the 2023 season in a deal for outfielder Alex Verdugo, the same trade that brought over current Red Sox reliever Greg Weissert.
If the Red Sox sign free agent Michael King, who has pitched the last two seasons for the San Diego Padres, they would be adding a five-year Yankee who was moved to San Diego in the trade that sent Juan Soto to the Yankees, if just for one season.
King Needs to Regain Health in 2026
“If Michael King were able to replicate his 2024 campaign in 2025, we would be talking about one of, if not the top free agent starting pitcher on the market,” Finkelstein wrote. “Once a relief weapon for the Yankees, in his first full season as a starting pitcher, King pitched to a 2.95 ERA with 201 strikeouts in 173 2/3 innings pitched.”
Injuries to a right-shoulder nerve as well as a knee in 2025 held King to just 15 starts with a 3.44 ERA and 76 strikeouts in 73 1/3 innings, but a return to health in 2026 could make the 30-year-old right-hander a solid signing in the free agent market for the Red Sox.
According to Finkelstein’s projection, King should snag a three-year deal worth $66 million, but with an opt-out after next season, meaning the Red Sox would likely not be locked into a multi-year commitment and King after a healthy season could test the free agent market once again.
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