The Yankees are arguably in the middle of one of their worst offseasons in a long time. Outside of bringing back Trent Grisham, they haven’t really made any moves that feel impactful. And that kind of mirrors what we’ve been seeing on the field, too. Since 2009, the Yankees still haven’t managed to capture another World Series!

Well, typically during George Steinbrenner’s era, the Yankees earned the nickname “the Evil Empire.” It was famously used by then–Red Sox president Larry Lucchino because they were always aggressive, always spending, and always landing the most prominent names. And why not? The franchise with the most World Series titles was the destination players dreamed of.

But now? That aura feels faded. As per former Yankee, Clint Frazier, “I am curious as to why some of these players may not want to sign there. Is it the fact that they don’t want to deal with what’s going on currently in there? Sonny Gray had comments. Devin Williams posted something on his Instagram story about saying… You sure had a lot to say whenever I didn’t sign back. So, you know, mixed opinions.”

Surely, the Yankees’ reputation doesn’t carry the same weight it once did, and it’s starting to show. Instead of being the prominent landing spot for star players, GM Brian Cashman seems to be running into roadblocks just trying to get big deals done. But why?

The answer lies in what a few players are saying.

“It feels good to me to go to a place now where you know what, it’s easy to hate the Yankees, right?” Gray said after landing in Boston. The reason may be his poor stint with the Yankees, where he had a  4.90 ERA from 130 innings. However, it was unimaginable a few years back that the players would mutiny against the Yankees.

Then there’s Devin Williams, who just completed his stint with the Yankees. “For a bunch of people that didn’t want me back on your team, y’all are sure mad in the DM’s.” So again, this complements Williams’s poor outing with the Yankees in 2025. Williams finished the season with a career-worst 4.79 ERA and surely faced huge fan criticisms.

Now, what makes the baseball scene in New York different from other parts is the constant media exposure and fans’ expectations. For instance, the Marlins’ clubhouse is not carrying the burden of expectations that the Yankees are. Talk about the ill factors of a big-market team! And that’s when, amid the on-field drought, players start to question being part of a team that’s all but winning.

It’s still too early to conclude on the Yankees

Even if it feels like the Yankees are at an all-time low right now, it’s still risky to completely write off a franchise that owns a record 21 World Series titles. Also, the offseason is only halfway done. There are still plenty of big names on the market — Kyle Tucker, Pete Fairbanks, Bo Bichette, and Cody Bellinger haven’t signed anywhere yet. And the Yankees are rumored to be in the mix for all of them.

On the other hand, instead of putting all the blame on a damaged reputation, it’s worth looking at how different things are at the top.

The contrast between George Steinbrenner and Hal Steinbrenner is pretty striking. Notably, under George, the Yankees fully embraced the Evil Empire label. But today’s leadership is clearly operating differently, with a much stronger focus on sustainability and long-term planning.

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Remember, Hal Steinbrenner recently mentioned wanting to keep the payroll under $300 million? That says a lot about how far the organization has shifted from its old, win-now mentality.

So, whether it’s the team’s reputation, a change in leadership philosophy, or even the pressure from fans, this offseason feels like it’s about more than just missing out on a few star players.