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Yankees head into free agency with heavy lifting to do — and one glaring hole to fill
New York Yankees pitcher David Bednar pitches against the Tampa Bay Rays during ALDS Game 3 at Yankee Stadium.
New York Yankees pitcher David Bednar (53) pitches against the Tampa Bay Rays during ALDS Game 3 at Yankee Stadium on Wednesday, Oct. 7, 2026, in New York.

The lockout that baseball has been headed toward seemingly for years is just about a month away, but until then, the industry will still move forward — including with the beginning of free agency at 5:01 p.m. Monday.

And few teams will be under more scrutiny than the Yankees — not just because they were knocked out by an AL East opponent in the ALDS for a second straight year, but because seemingly the entire organization appears to be up for debate.

Hal Steinbrenner already opted for stability when he decided to bring back GM Brian Cashman on a new deal. Though Aaron Boone will be back in the dugout, the manager has not gotten a contract extension and stands to enter 2027 in the final year of his contract.

Pitching coach Matt Blake will return, but Steinbrenner made clear his displeasure about the team’s offense following their ouster in a sweep by the Rays.

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