?Will GM Brian Cashman’s fresh contract keep New York’s front office steady?
With manager Aaron Boone back for another year, the Yankees will pair their on‑field skipper with the veteran GM. New York clinched the AL’s top wild‑card berth and swept Boston in that round, only to be blanked by the Rays in the ALDS, the eventual league champion.
Cashman, who has steered the club since 1998, is the longest‑serving executive in baseball. His current deal covers 2023 through this season, and extending it was hardly shocking given his tenure and past success. The Yankees’ historic reluctance to negotiate extensions likely delayed finalizing the pact.
The Bronx squad fell in the divisional round for two straight years, each time to the AL’s eventual World Series team. Owner Hal Steinbrenner refused to blame Aaron Boone or Cashman, pointing instead to a sputtering offense. “I don’t think you can pin the season and the unacceptable end to it on Aaron,” he told reporters, adding, “I don’t think you can pin it on Brian Cashman.”
After posting nine runs in both games against Boston, the Yankees managed only five runs in three contests with Tampa Bay. Game 1 featured a Drew Rasmussen gem that carried a no‑hitter into the eighth inning. In a sloppy Game 2 loss, New York recorded more errors (4) than hits (3).
The scoring drought wasn’t limited to October. When Aaron Judge exited in late May, the club slipped to 25th in runs scored over the next three months, matching the Angels for the league’s lowest wRC+ from June through August. Though Judge’s comeback was brief, the Yankees rose to a middle‑of‑the‑pack offense by September.
Cashman faces several offseason puzzles. Closer David Bednar and second baseman Jazz Chisholm Jr. hit free agency, and a qualifying offer could repeat the Trent Grisham misstep. The pitching staff, anchored by Gerrit Cole, Carlos Rodón and Max Fried, is edging into their mid‑30s, while Clarke Schmidt approaches age 31. In my view, Cashman must act fast to shore up the aging rotation.
Health questions also loom for Judge and Giancarlo Stanton. Judge’s attempt to return from a calf strain in the playoffs never materialized, and Stanton missed most of the regular season with a lower‑leg issue, though he appeared in the postseason. If both regain full fitness, the lineup could become a juggling act with Luis Garcia Jr. and Ben Rice also vying for first‑base/DH duties.
Will the Yankees’ roster overhaul catapult them back into the AL pennant race next year?

