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ST PETERSBURG, FLORIDA – OCTOBER 05: Manager Aaron Boone #17 of the New York Yankees looks on from the dugout out before game two of the American League Division Series against the Tampa Bay Rays at Tropicana Field on October 05, 2026 in St Petersburg, Florida. (Photo by Mike Stobe/Getty Images)
The New York Yankees fell short once again this season, getting swept by the Tampa Bay Rays in the ALDS roughly two weeks ago.
One of the biggest questions entering the offseason was whether the Yankees would keep Aaron Boone as their manager with one year remaining on his contract after completing his ninth season.
That question was answered Monday when Pete Caldera of USA Today first reported that the Yankees would retain Boone for the 2027 season but would not give him a contract extension.
Michael Kay Drops Blunt Quote on Yankees Keeping Boone
During Tuesday’s episode of the “Michael Kay Show,” YES Network announcer Michael Kay shared his thoughts on the Yankees keeping Boone.
Kay made it clear that he believes this is Boone’s last chance. If he doesn’t win a World Series, Kay expects the Yankees to fire him.
“Now I will tell you this about Aaron Boone. So he’s coming back. And I believe this is the last chance saloon. I believe that if he doesn’t win a World Series in 2027 he will be let go,” Kay said. “And they’ll move onto another manager. 10 years is a long, long time. And 10 years is an eternity with the New York Yankees when it comes to not winning a World Series.
“So he’s gotta win. They’re not gonna have him go into the season and give him an extension… too bad. Now he knows he either wins a World Series or he’s not coming back. And can I swear to that, no I can’t swear to that.”
ICYMI: Aaron Boone is back as New York Yankees’ manager. Will this be his last chance to win a World Series?
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Looking at the Yankees
New York is in an interesting spot and will likely confirm Boone’s return for 2027 during a press conference Wednesday.
Even with Boone coming back, the Yankees still have major questions to answer about their roster. They have some glaring holes and need to make improvements to compete with teams like the Rays, who had New York’s number all season.
That said, the Yankees also dealt with extended absences from sluggers Aaron Judge and Giancarlo Stanton. The offense took a significant dip when they were out of the lineup, particularly Judge.
New York will have an opportunity to retool the roster around Judge this offseason, with several players set to hit free agency. That will give the Yankees a chance to explore the open market and identify areas for improvement, particularly at third base, second base, catcher and center field.
Cole Sullivan Cole Sullivan is a sports journalist for Heavy.com covering the NFL, NBA, college football, and college basketball. A member of the United States Basketball Writers Association, he has written for FanSided, Athlon Sports, The Sporting News, and Newsweek. Sullivan earned an Associate degree from Franklin Pierce University and a Bachelor’s degree from Lynn University, where he studied Communications and Media Studies with a focus on Sports Journalism. More about Cole Sullivan