Thirty years at the same desk
He was 31 when George Steinbrenner hired him. The Yankees owner used to fire executives the way other people change shirts. Brian Cashman stayed put.
He is 59 now. According to the New York Post, which broke the story on Friday, he is set for a 30th season in 2027. His deal is up. Hal Steinbrenner, the son, has no real reason not to hand him another one.
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Never once below .500
The first big move came on February 6, 1998: Cristian Guzman, a future All-Star, plus three prospects to the Minnesota Twins for infielder Chuck Knoblauch. Twenty-eight years later, the list runs long.
Under Cashman, the Yankees have never finished a season under .500. Not once. Four World Series, seven American League pennants, 15 AL East titles. Nine of those division crowns came consecutively in his first nine seasons, with Joe Torre in the dugout. Across 29 seasons, New York has missed the playoffs five times.
That kind of run barely exists in American sport now. Front-office chiefs last four or five years. Cashman has outlasted two owners, a stadium rebuild and around a dozen roster cycles.
The real issue is Aaron Boone
The next call is less comfortable. Cashman and Hal Steinbrenner have to decide what happens with the manager after the season. The Yankees are on course for an eighth playoff berth in nine years under Boone. On paper, that reads well.
The title never comes, though. One wild-card exit, three Division Series defeats, two losses in the championship round. Then the 2024 loss to the Dodgers in five games. New York’s last crown was 2009.
Keeping a 59-year-old executive who has not won a ring in 17 years can be sold on his record and the calm he brings. It sells less well in the Bronx, where patience has never been part of the deal. Cashman looks safe. Boone does not.
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