Yankees Showing the Title Drought Is Under Their Skin at MLB GM Meetings

Criticism stirs a response

The Yankees’ standard is clear: seasons without a World Series title are considered failures. Their latest ended with a sweep by the Tampa Rays in the American League Division Series, extending a title drought that began after their 2009 championship.

At the 2026 MLB general managers’ meetings in Las Vegas, Cashman addressed criticism from Derek Jeter, Alex Rodriguez, Goose Gossage and Jorge Posada. The former Yankees said the team’s season ended against a small-market AL East rival and questioned whether the organization had become soft and less committed to winning.

Cashman said the criticism could anger him and prompt him to question what critics meant. He also recognized that attention reflects fans’ and others’ hopes for the team.

A record to live up to

The Yankees have won 27 World Series titles, 41 American League pennants and made 61 postseason appearances. They have reached the postseason in nine of the past 10 seasons, but have not won the championship since 2009.

The current drought is approaching two decades. The team has not gone this long without a title since the 18-year span between championships in 1978 and 1996. Cashman said the organization is always trying to live up to its history, with delivering a championship as its most important goal.

Cashman faces the spotlight

Cashman remained with reporters for more than an hour on Tuesday in Las Vegas, answering questions. He described the media attention as constant, but said it comes from people who hope the team can improve.

He said he would continue working to push the Yankees toward better results. The pressure, he added, is part of the role in the nation’s largest media market.

Winter plans face uncertainty

Cashman is preparing to build another championship roster, though a possible lockout starting Dec. 2 could delay the process. He said he was proceeding with business as usual until told otherwise, working within a budget set by owner Hal Steinbrenner.

A person briefed on the Yankees’ plans told FanSided that Cashman’s ideal offseason would include trading for San Diego Padres closer Mason Miller, signing free agent second baseman Brandon Lowe and adding a catcher to support or replace Austin Wells. The Yankees are also at least interested in left-hander Tarik Skubal. Cashman said the team had begun contacting clubs and agents to assess what was feasible and plan from the information gathered.