Yankees’ World Series Pitcher Sends Red Sox Ultimatum After Contract Update

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The Boston Red Sox could soon face a difficult bullpen decision involving a veteran reliever who spent six seasons with the New York Yankees.

Tommy Kahnle, who signed a minor-league deal with Boston during spring training, has dominated at Triple-A Worcester while waiting for a return to the majors. But with a June 1 opt-out clause approaching, the 11-year veteran said he was prepared to force the organization’s hand.

And the timing could be significant for a Red Sox club that recently lost key reliever Garrett Whitlock to the injured list and has received inconsistent performances from parts of its bullpen.

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Kahnle has been one of the most effective relievers in the International League this season and the 36-year-old’s performance has generated speculation that he could soon join Boston’s major league bullpen. However, the veteran is apparently unwilling to wait much longer.

MassLive’s Chris Cotillo recently reported that Kahnle is expected to pursue other opportunities if he is not promoted before his opt-out date.

“According to a source with knowledge of Kahnle’s thinking, the righty ‘100 percent’ plans to hit free agency if he is not added to Boston’s roster,” Cotillo wrote. “The Red Sox can prevent such a move by selecting Kahnle’s contract and adding him to their bullpen ahead of Tuesday’s series opener against Baltimore (or earlier).”

Kahnle spent parts of six seasons with the Yankees across two stints and was a key contributor to several postseason teams in New York and pitched during the team’s 2024 World Series loss to the Los Angeles Dodgers. He also saved nine games for the Detroit Tigers in 2025 after signing a one-year, $7.75 million contract.

“This is the second time Boston has faced a roster decision with the right-hander, who triggered an upward mobility clause on May 1, but ultimately remained in the minors with the organization,” MLB Trade Rumors’ Charlie Wright noted after Cotillo’s update on Kahnle’s ultimatum.

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Now, after months of waiting in Triple-A, Kahnle appears ready to make Boston choose between a roster move and losing one of its most effective relief pitchers. And Boston is clearly aware of the stakes.

“I know there are dates coming up,” Tracy told Cotillo. “Our front office, they’re always aware of that. We’re well-aware of who he is, what he’s done and his performance down there.”

That puts pressure on a Red Sox front office that must decide whether to clear both a 26-man and 40-man roster spot for the veteran right-hander.

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