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Red Sox Lose 26-Year-Old Pitcher To Yankees In Free Agency

The New York Yankees and Boston Red Sox both love when they can claim to have the upper hand, not only on the scoreboard, but in the transactions between the two teams.

Yankees fans loved when Johnny Damon and Jacoby Ellsbury chose to sign with New York in free agency. Red Sox have enjoyed the recent breakout of catcher Carlos Narváez, who the Yankees traded to them in December, not to mention Aroldis Chapman’s late-career resurgence.

Recently, one more Red Sox player chose to leave for the Yankees in free agency, but it received far less fanfare.

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Yovanny Cruz heads to Yankees on minor-league deal

Feb 18, 2025; Lee County, FL, USA; Boston Red Sox pitcher Yovanny Cruz (82) participates in media day at JetBlue Park at Fenway South. Mandatory Credit: Nathan Ray Seebeck-Imagn Images | Nathan Ray Seebeck-Imagn Images

Right-handed pitcher Yovanny Cruz was one of a large handful of Red Sox players to elect free agency on Nov. 6, the unofficial day the 2025 season ended and 2026 began, for roster-building purposes. But he wasn’t out of work for long, because the Yankees snapped him up.

Cruz and the Yankees agreed to a minor-league deal for next season, according to the transactions log on the 26-year-old’s official roster page. The signing became official on Nov. 8, but it took at least a few more days to be reflected on his page.

Cruz spent the entire season with Double-A Portland, and he looked excellent. He put up a 3.04 ERA in 34 appearances, all out of the bullpen, and struck out 72 batters in 59 2/3 innings. If there was one blemish on his resume, it was his 44 walks, a number he’ll need to cut down against better competition.

It’s rare that a pitcher lasts nine years in the minors, as Cruz has, while never progressing past Double-A. Cruz initially signed as an amateur out of the Dominican Republic with the Chicago Cubs in 2016, and has since played in the San Diego Padres organization and the Dominican Winter League for Estrellas Orientales.

Since Cruz has yet to make his major league debut, he maintains his rookie eligibility and all of his minor-league options. But he’s reached a point in his career where he can leave in free agency at the end of every season unless he progresses to the majors and gets a guaranteed contract.

The odds would indicate that this particular transaction isn’t likely to hamper the Red Sox long-term, but there’s always that small chance it does.

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