The crucial decisions looming over Yankees’ offseason as title drought hits historic stretch

The New York Yankees are facing six critical organizational and roster decisions this offseason following an ALDS sweep by the Tampa Bay Rays. The loss extends the franchise's World Series championship drought to 17 years, marking their longest stretch without a title since 1923. Facing potential industry turbulence with an expiring collective bargaining agreement on December 1, team leader Aaron Judge publicly urged the front office to go all-in to address personnel holes.

Dan Martin details key questions regarding the leadership status of general manager Brian Cashman and manager Aaron Boone. Additionally, the front office must address impending free agents such as closer David Bednar, evaluate underperforming position players like Jazz Chisholm Jr. and Trent Grisham, and address roster questions surrounding infield configuration, catching upgrades, and bullpen depth.