With the Toronto Blue Jays knocking the New York Yankees out of the postseason on Wednesday night, it’s clear that the Yankees, when the October lights hit, are once again not among the elite teams in Major League Baseball. No one is more to blame for that than senior vice president and general manager Brian Cashman. Cashman is the longest-serving GM in Yankees history and has the longest tenure among his MLB peers, serving in his role since 1998. During that time, the Yankees have racked up more than 2,500 regular-season wins and earned four World Series titles. It’s an impressive history, but it’s also one that should come with a bit of nuance as well. The last World Series win for the Yankees came in 2009, and the storied franchise has been back to the Fall Classic just once since then, falling short against the Los Angeles Dodgers last year. Around that one World Series appearance has been numerous postseason disappointments with talented teams and hefty payrolls, including this year’s Yankees team that
