September gave New York sports fans a reason to believe history might repeat itself. The last time the New York Giants and Jets both won their season openers in 2009, the Yankees went on to capture their 27th World Series title. And with both NFL teams once again opening their seasons with victories in 2026, the Bleacher Creatures had a nostalgic reason to dream. But the Bronx Bombers failed to deliver, crashing out of the postseason as their championship drought stretched on.

Now, the Yankees’ growing wait for another title is drawing an uncomfortable comparison with the Jets’ years of disappointment. And according to a WFAN Sports Radio personality, the Bronx Bombers may be approaching a point where the mockery they face rivals that of their struggling football neighbors.

“Why would you expect that to change next year or the year after that or the year after that, right? It’s a long time. It is a long time. When you start contemplating where you were and all the things that have changed in your lifetime since you last celebrated your favorite team’s championship. Like we mocked the Knicks for it, rightfully so, until they won last year. It is a little different. I think the Yankees mocking should begin,” Craig Carton said via WFAN Sports Radio.

The Yankees’ 17-year World Series title drought equals the franchise’s previous 17-year championship drought, which lasted from 1979 to 1995. Despite boasting 34 consecutive winning seasons and one of the highest payrolls in MLB, the organization has repeatedly collapsed in October due to structural roster imbalances, situational hitting failures, and a persistent inability to overcome key rivals.

The closest they came to the ring was in 2024 when they secured a World Series berth against the Los Angeles Dodgers. But they were undone by fundamental blunders. In the decisive Game 5, holding a 5-0 lead, a historic defensive meltdown, comprising dropped flies, missed coverage at first base, and catcher interference, gifted the Dodgers a 5-run inning and the title.

This year, despite managing 93 regular-season victories, the Yankees were entirely swept by a low-payroll division rival, the Tampa Bay Rays. The team never once held a lead during the entire series, a franchise first, prompting harsh criticism from former stars like CC Sabathia regarding a lack of clubhouse leadership and accountability.

This forced Carton to draw a comparison with the Yankees’ NFL cousin, the Jets. The Jets have an all-time championship drought of 57 years, having not won a title since Super Bowl III in the 1968 season, when they defeated the Baltimore Colts.

However, WFAN Radio host Chris Mcmonigle thinks it’s still too early to keep the Jets and the Yankees on the same bench. “The Jets haven’t made the playoffs since the day of your last son’s birth. Think of that… That’s a playoff drought. Not a World Series drought. And the Yankees don’t even have a World Series drought. They were in it two years ago… The Yankees are getting into that ballpark, my friend, because there’s an expectation that the Yankees are better.”

The Yankees, despite not winning the World Series since 2009, have appeared in the playoffs 13 times so far. By contrast, the Jets’ last playoff appearance was in 2010 when they lost in the AFC Championship Game to the Pittsburgh Steelers. So, the struggles for the teams are certainly not the same.

Yet the Yankees crashing out of the playoffs year after year suggests they are entering the Jets’ territory sooner than expected.

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