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New York Yankees vs. Kansas City Royals New York Yankees catcher Austin Romine talks with starting pitcher Sonny Gray in the eighth inning against the Kansas City Royals on Sunday, May 20, 2018, at Kauffman Stadium in Kansas City, Mo. (John Sleezer Kansas City Star TNS) KANSAS CITY MO USA EDITORIAL USE ONLY Copyright: xx 1231588 JohnxSleezerx krtphotoslive828719
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New York Yankees vs. Kansas City Royals New York Yankees catcher Austin Romine talks with starting pitcher Sonny Gray in the eighth inning against the Kansas City Royals on Sunday, May 20, 2018, at Kauffman Stadium in Kansas City, Mo. (John Sleezer Kansas City Star TNS) KANSAS CITY MO USA EDITORIAL USE ONLY Copyright: xx 1231588 JohnxSleezerx krtphotoslive828719
For a player who never wanted to be in New York, Sonny Gray is wasting no time embracing Boston’s favorite pastime: taking shots at the Yankees. The Red Sox’s $41 million signing from the Cardinals is making it clear where his loyalties now lie.
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In a recent interview, Sonny Gray exclaimed, “I never wanted to go there in the first place… but I do appreciate my time there,” when asked about his time in New York.
To add fuel to the fire, during the interview at his Boston media introduction, Gray wore a 2007 World Series cap, signaling ambition. He emphasized the importance of joining a “super competitive market” and competing for the 2026 World Series.
Sonny Gray holds a 2-3 record with a 4.15 ERA against the New York Yankees.
In his 8 career appearances versus New York, he has recorded 48 strikeouts. Despite a slightly elevated ERA, his strikeout rate demonstrates effective pitching against the rival.
Sonny Gray says he did not have a good experience with the Yankees:
“I never wanted to go there in the first place… but I do appreciate my time there.”
— Gabrielle Starr (@gfstarr1) December 2, 2025
His arrival in Boston positions him in direct competition with the Yankees moving forward.
Those past battles will now take on new intensity as Gray prepares to face his former team from the other side of baseball’s most heated rivalry. Probably another 2007 WS win is around the corner for the Boston Red Sox.
The Red Sox can add more power around Sonny Gray
The Boston Red Sox keep insisting they’re ready to compete again, and maybe they actually believe it. Sonny Gray has arrived, and the rotation feels sturdier. But if this is really the turning point, then they’d better act like it.
Other than Gray, two clear trade targets stand out in Boston talks today.
Joe Ryan, who delivered 4.5 WAR with a 3.42 ERA over 171 innings last season, could be a prime target despite posting a 6.47 ERA over his final seven starts amid trade rumor chaos. Ryan could easily align himself with what Boston needs.
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The other one is Freddy Peralta. Peralta brings 5.5 WAR, a 2.70 ERA, and 176.2 innings pitched last season. He struck out 200-plus in each of the previous three seasons. Meanwhile, Milwaukee accepted Brandon Woodruff’s offer and holds young arms ready behind Peralta today.
Boston knows Gray alone will not close the growing gap in this division. Peralta or Ryan would signal intent and remind rivals that patience has limits. The market is moving, and the Red Sox cannot simply admire it forever.