The New York Yankees take great pride in saying that any season that doesn't end in a World Series title is a failure.

That is an incredibly high standard to set, and the Yankees haven’t won the Fall Classic since 2009. So, by their count, the Yankees are on a streak of 17 consecutive failed seasons, including being swept in an American League Division Series by the Tampa Rays to end 2026.

Given the Yankees’ grandiose expectations, they shouldn’t get too upset about criticism from outside sources. Yet it is becoming an annual tradition for the Yankees’ Brian Cashman to snap back at the critics during the MLB General Managers Meetings.

Cashman claps back at the critics

Cashman was at it again earlier this week when the GMs held their 2026 conclave at the Aria Casino & Resort in Las Vegas. He was ready to respond to criticism from Yankees legends Derek Jeter, Alex Rodriguez, Goose Gossage and Jorge Posada that New York’s season ended against their small-market AL East rivals and that the organization has become soft and not committed to playing winning baseball.

“It can make you angry,’’ Cashman said. “It can make you re-evaluate things. It can make you question things, question the individuals, like ‘What do you mean by that?’”

Yet it comes with the territory. The Yankees’ 27 World Series titles are easily a record, and they have won 41 AL pennants and made 61 postseason appearances, including nine in the last 10 seasons.

“The Yankees mean a lot to a lot of people, whether it's the people that are throwing complaints, or throwing allegations, or our fans who are upset,” Cashman said. “We know we have a history of success that we're always trying to live up to. We're having a lot of things that we're always trying to do the best of our abilities, and the most important one is to deliver a championship.”

Yankees’ championship drought is at 17 years

The championship drought is nearing two decades. The Yankees haven’t gone this many seasons without winning it all since the 18-year gap between titles in 1978 and 1996.

While Cashman might appear a little thin-skinned at times, he does understand the expectations that come with playing in the nation’s largest media market. Cashman didn’t duck reporters on Tuesday in Las Vegas, standing there for over an hour until every question had been answered.

“I mean, got a cattle prod constantly stuck right where you don't want it, nonstop with electrodes going,” Cashman said of the constant media attention. “So that keeps you alive. But you also, when you take a step back, you got to channel and recognize it's coming from a place of hope and love of wanting things to be better than they currently are, and so that's where we're constantly trying to push to get to.”

Cashman will try to put together a championship roster again this winter, though the impending lockout on Dec. 2 could delay those plans. While the Yankees are at least interested in left-hander Tarik Skubal, a person briefed on the team’s plans told FanSided that Cashman’s perfect offseason scenario would be to trade for San Diego Padres closer Mason Miller, sign free agent second baseman Brandon Lowe and add a catcher to supplement or supplant Austin Wells.

“I’m approaching business as usual here until told otherwise,” Cashman said. “I’ve been given a budget by (owner Hal Steinbrenner), and we’re trying to now connect with teams and agents as the winter has just started to see what is feasible and what isn’t feasible and try to game plan off of that information that we’re gathering now.”