​NEW YORK, NY – DECEMBER 06: (L-R) Managing General Partner, Co-Chairperson Hal Steinbrenner, Senior Vice President, General Manager Brian Cashman and Aaron Boone pose for a photo at Yankee Stadium on December 6, 2017 in the Bronx borough of New York City. (Photo by Mike Stobe/Getty Images) GettyTORONTO, ONTARIO – OCTOBER 05: (L-R) Brian Cashman, Senior Vice President and General Manager of the New York Yankees, and Aaron Boone #17 of the New York Yankees speak before game two of the American League Division Series against the Toronto Blue Jays at Rogers Centre on October 05, 2025 in Toronto, Ontario. (Photo by Mark Blinch/Getty Images) GettyST 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) GettyNEW YORK, NEW YORK – OCTOBER 07: Manager Aaron Boone #17 of the New York Yankees signals toward the bullpen during the eighth inning in game three of the American League Division Series against the Tampa Bay Rays at Yankee Stadium on October 07, 2026 in the Bronx borough of New York City. (Photo by Caleb Bowlin/Getty Images) GettyTORONTO, ONTARIO – OCTOBER 05: Brian Cashman, Senior Vice President and General Manager of the New York Yankees, looks on before game two of the American League Division Series against the Toronto Blue Jays at Rogers Centre on October 05, 2025 in Toronto, Ontario. (Photo by Mark Blinch/Getty Images) GettyBRONX, NEW YORK – DECEMBER 21: New York Yankee general manager Brian Cashman speaks to the media during a press conference at Yankee Stadium on December 21, 2022 in Bronx, New York. (Photo by Dustin Satloff/Getty Images) GettyThe New York Yankees had yet another disappointing season, getting eliminated in the American League Division Series by a division rival for the second-straight year. The Tampa Bay Rays completed a 3-0 sweep over the Yankees with a 4-3 win at Yankee Stadium on Thursday. Tampa Bay will play in the American League Championship Series. Naturally, many are wondering if Boone’s and Cashman’s jobs are safe. The Yankees haven’t won a World Series since 2009, which is a big drought for a historic franchise like New York. This morning, Buster Olney addressed the future of Cashman and Boone on ESPN. Aaron Boone, Brian Cashman Expected to Stay With New York Yankees After ALDS LossGettyTORONTO, ONTARIO – OCTOBER 05: (L-R) Brian Cashman, Senior Vice President and General Manager of the New York Yankees, and Aaron Boone #17 of the New York Yankees speak before game two of the American League Division Series against the Toronto Blue Jays at Rogers Centre on October 05, 2025 in Toronto, Ontario. (Photo by Mark Blinch/Getty Images)
Underscore Media’s Jimmy Traina wrote on X: Buster Olney just said on ESPN that he expects the Yankees to re-sign Cashman this offseason