Yankees eliminated from MLB playoffs: Could Brian Cashman, Aaron Boone’s stability be part of the problem?

The franchise of George Steinbrenner, who once changed managers 11 times in a five-year span from 1978-82 and cycled through eight general managers in 11 years from 1978-88, is now a model of stability. In the last 28 years, the Yankees have had one general manager (Brian Cashman) and three managers (Joe Torre, Joe Girardi, Aaron Boone). That’s almost unheard of continuity.

On one hand, the continuity is justified. The Yankees have not had a losing season since 1992 and they’ve made the postseason eight times in the last nine years. They won the AL East title in 2022 and 2024, and finished tied for the division’s best record this year, but lost on a tiebreaker. It’s not as easy as spending money = winning (see: The Mets), yet the Yankees consistently win.

On the other hand, the Yankees were again eliminated by a team they should be measured against this postseason. Wednesday’s loss to the Toronto Blue Jays in Game 4 of the ALDS (TOR 5, NYY 2) sent the Yankees home for the winter and the Blue Jays to the ALCS. It was a lopsided series. The Blue Jays outscored New York 34-19 and outhomered them 9-3 in the four games.

The Yankees have consistently won in the regular season and against AL Central teams in the playoffs, but too often in the Boone/Cashman era have short against other top high-spending clubs (Blue Jays, Houston Astros, Los Angeles Dodgers, etc.). Some numbers on New York’s postseason success in Boone’s eight years as manager:

• Postseason record: 25-27 (.481)
• Record vs. AL Central teams: 15-4 (.789)
• Record vs. all others: 10-23 (.303)

I don’t mean to pick on the AL Central, but the fact of the matter is that division houses five teams that do not run large payrolls and are often the underdog in a postseason series against non-division rivals. The Yankees have bullied the Cleveland Guardians, Minnesota Twins, et al in October. Against teams more on their level, they consistently come up short.

The Yankees were eliminated by the Astros in 2017, the Red Sox in 2018, the Astros in 2019, the Red Sox in 2021, the Astros in 2022, the Dodgers in 2024, and the Blue Jays in 2025. When it happens two or three times, it’s frustrating, but it’s baseball. We now have almost of a decade of evidence that against top competition on the game’s biggest stage, the Yankees aren’t up to the task.

Stability is a good thing and something teams crave. It works for the Yankees because they’re in the race just about every season. It also hasn’t worked because their season keeps ending the same way. The Yankees will never be judged by their regular season and early October success. After this many years, it’s fair to ask whether this leadership group can get them over the hump.

There is not much reason to expect the Yankees to replace Boone, who in February signed a two-year contract extension that begins next season. There are a lot of careless mistakes with this team though, and a lot of questionable decisions in October. That reflects poorly on the manager. Eight years is a long time for any manager and yet Boone seems likely to get a ninth. 

Cashman is about as secure as any head baseball operations executive in the game (his last name might as well be Steinbrenner). It’s hard to see him going anywhere. The team’s stability and continuity also applies to Cashman’s department heads, including scouting director Damon Oppenheimer (in place since 2005) and analytics department head Michael Fishman (hired in 2005).

The notable front office hires the Yankees have made from outside the organization in recent years are baseball lifers Cashman considers among his mentors, including former general managers Jim Hendry, Omar Minaya, and Brian Sabean. They’re all with the Yankees as advisors. It wouldn’t be a bad idea for the Yankees to branch out a bit and make more outside hires just to bring in new voices and new perspectives.

To be sure, the Yankees have hired bright people away from other organizations in recent years. Pitching coach Matt Blake and director of pitching Sam Briend overhauled the team’s pitching development, which is now among the best in the game. Jarret DeHart was brought in to do the same on the hitting side last winter. Countless others have cycled through over the years.

At some point, though, you do have to ask yourself why your process leads to the same result year after year. The Yankees love to tout their process (so does every team), but it is a results-based business, and the results aren’t there, at least not in October. The Yankees can get there. How do they go further? Can they while maintaining the status quo? Evidence is mounting they can’t.