The partnership between Brian Cashman, general manager of the New York Yankees, and manager Aaron Boone remains one of the longest in Major League Baseball. Since Boone replaced Joe Girardi after the 2017 season, the Yankees have won three American League East titles and reached the AL Championship Series three times. The team returned to the World Series in 2024 for the first time since their last championship in 2009.
Despite these achievements, there is ongoing pressure for results. If the Yankees do not win this year’s World Series, it would mark a 17-season drought—matching their longest period without a title since Babe Ruth joined over a century ago.
Aaron Boone addressed this situation recently: “[Not winning the World Series] bothers me a lot. It’s definitely as big a motivator and what drives me to still do this as much as anything … that chase to ultimately get No. 28 is as big a reason as any, and it does bother me.”
The Yankees are largely keeping last year’s roster intact following their loss to Toronto in four games during the 2025 AL Division Series. They made key moves at last year’s trade deadline by improving their bullpen with closer David Bednar and expect pitchers Gerrit Cole and Carlos Rodón to return from injury later this season. Cody Bellinger was re-signed on a five-year contract after being one of the team’s top contributors behind Aaron Judge.
Brian Cashman has challenged critics who question whether his team can compete for another championship: “I’ve been openly willing to challenge anybody that [says] we don’t have a championship-caliber roster and team.”
Last season, New York won 94 regular-season games—tied with Toronto for most in the American League—but struggled against playoff-bound teams, finishing with a losing record (28-34) against them. Against Toronto specifically, they went 5-8 during regular play and lost again in postseason competition.
Another point of concern is New York’s recent performance when facing elimination or closeout scenarios; over their past three decisive postseason series—including losses to Houston (2022 ALCS), Los Angeles (2024 World Series), and Toronto (2025 ALDS)—the Yankees are just 2-11.
Both Cashman and Boone maintain confidence in their current roster’s ability: “championship-caliber” is how they describe it.
The new season opens March 25 in San Francisco. The organization aims for its 28th World Series title—and hopes to avoid matching its historic championship drought.
