Most pressing Yankees questions for Brian Cashman at GM meetings

For disconsolate Yankees fans, consider the depths of this time on the calendar last year.

Brian Cashman held court at the GM meetings in Scottsdale, Ariz., where he forcefully defended the club’s operations following an 82-win season and said that the Yankees’ processes and people were “pretty f—ing good.” 

After a 2024 that fell three wins short of a World Series title, the temperature will be turned down at this year’s meetings in San Antonio, but questions remain about a championship drought that has reached 15 years for a team entering another pivotal offseason. 

For the first time since the club’s hopes ended in a wild Game 5 against the Dodgers on Wednesday, Cashman will speak publicly about a season that marked improvement but not enough for a franchise that has made World Series championships — and not appearances — its standard. 

Baseball executives are expected to arrive in Texas on Monday ahead of the official start of the meetings Tuesday.

By the time the meetings conclude Thursday morning, there should be more clarity on how the Yankees plan to handle this offseason, with Cashman set to answer questions such as: