Across all 30 MLB teams, Brian Cashman is probably the GM who takes the most heat from fans and insiders. And a big part of that criticism stems from the Yankees’ long World Series drought since 2009. Because of that, he often ends up in the spotlight, whether it’s about signing new players, making roster decisions, or standing by his manager.

“The reason we’re able to adjust and change is because I am very open-minded, and I challenge our staff to be the same way. If someone’s doing something better than we are, we have to figure that out as fast as we possibly can, and then adapt and adjust and grow because of it,” Cashman said in an interview with Fox Sports.

Now that Cashman has finally broken his silence, it might start to change the conversation around him and the perception of how the Yankees are run.

One of the most common accusations aimed at the Yankees and their GM is that they’re reluctant to change. It is often argued that while a few other teams across MLB are constantly evolving, the Yankees and Cashman tend to be stubborn and slow to adapt.

For instance, the Los Angeles Dodgers, the back-to-back WS champions, are not stopping to improve. This offseason, they signed the biggest free agent in the sport, Kyle Tucker, to a 4-year, $240 million contract. His power, high-level defense, and consistency would only strengthen LA’s already star-studded lineup.

In fact, to identify gaps, LA uses high-level scouting and data-driven analytics. Their scouting report was dead on against the Yankees in 2024. It mentioned that the Yankees were not just the majors’ worst baserunning team by every metric, but the difference was vast on the field between them and the Padres, who the Dodgers beat in the NL Division Series.

This metric reportedly had the Bronx Bombers as the worst-positioned outfield. They were amazed by how many times relay throws came skittering through the infield with no one taking charge and how often Jazz Chisholm Jr., for example, was out of place or just standing still when a play was in action.

But according to Cashman, the reality is quite different.

Over the years, he has reportedly built relationships with executives from other sports.

He has connections with Julien BriseBois of the Tampa Bay Lightning and Howie Roseman of the Philadelphia Eagles.

They regularly exchange articles on leadership and share ideas about improving their organizations. Per Cashman, he’s always curious about perspectives from outside baseball and looks for ways to bring those ideas into the Yankees’ operations.

Former Yankees manager Buck Showalter even backed that up, saying Cashman has consistently tried to keep the Yankees “relevant, current, and modern.”

According to Cashman, initiatives such as adding a health and wellness center at the ballpark, expanding the batting cages, and creating a player lounge encourage players to spend more time at the stadium. But why did he choose to stay silent despite the fans’ emotion, which goes against him?

“I’ve learned over the course of time that it doesn’t matter what you say. What do you do? I can try to fight like Don Quixote with the windmills out there and all those battles all the time. But is that really an efficient use of my time?”

Call Cashman stubborn or adamant, but in reality, he means business. And that mindset has helped him remain one of the longest-serving GMs in baseball, holding the position with the Yankees since 1998.

Brian Cashman is here to stay with the Yankees

For a historic franchise like the Yankees, a 16-year World Series drought would normally be enough to cost a GM his job. Many would assume Brian Cashman should have been shown the door years ago. But the numbers tell a different story.

Reportedly, since Cashman took over as GM, the Yankees have posted a winning record for 33 straight seasons, the second-longest streak in MLB history, trailing only the franchise’s own 39-season run from 1926 to 1964. That kind of consistency is a big reason ownership has continued to stand by him.

Even Hal Steinbrenner knows where the organization’s real strength came from.

Despite all the criticism surrounding Cashman, it’s clear he isn’t going anywhere anytime soon. When asked about how long he plans to stay with the Yankees, Cashman himself admitted he doesn’t have a clear answer.

“I have no idea.”

Still, the perfect ending to Cashman’s tenure would obviously be another World Series title after their 27th one in 2009. And whenever he does eventually step away, his long run with the Yankees will almost certainly put him in the conversation for a place in Cooperstown.