For years, the New York Yankees have done their best to shed the “World Series or bust” label that put the franchise in a pressure cooker immediately after the dynasty years. After capturing four titles in five years from 1996-2000, the Yankees would make the Fall Classic in 2001 and 2003, but fell short. Owner George Steinbrenner deemed those seasons failures.

Harsh? Sure. We’d agree. But what has followed since? One championship since 2001. Two World Series appearances since 2004. The most embarrassing playoff collapse in history (2004 ALCS vs Red Sox). The worst loss in a World Series clinching game ever (Game 5 vs Dodgers in 2024). And excuse after excuse, especially as we’ve endured the interminable Brian Cashman/Aaron Boone era. Under that duo, the pendulum of championship expectations and swung aggressively in the opposite direction.

Once again, when they were eliminated in 2025 at the hands of the division-rival Toronto Blue Jays — who are now headed to their first World Series since 1993 after defeating the Seattle Mariners in Game 7 of the ALCS on Monday night — they told their fans that the playoffs are a crapshoot.

The Blue Jays likely fall under the “crapshoot” category the Yankees are referring to, given the fact they haven’t made an ALDS since 2016, but they added to the fringes of their roster better than the Yankees ever could. They focused on chemistry. They orchestrated the most comeback victories (50) in MLB this year. They prioritize contact (.265 batting average led MLB) and limit strikeouts (1,099 strikeouts was second-fewest in MLB). Meanwhile, the Yankees haven’t changed their overall blueprint in … we don’t know how long.

When Joel Sherman of the New York Post asked what the missing ingredient was for this team to go all the way, both Aaron Boone and Brian Cashman all but essentially shrugged, claiming all they needed to do was keep assembling good teams and then merely hope “everything lines up” once the calendar flips to October.

We’d agree … if the Yankees were a mid-market team with a $150 million payroll. With limited resources, yes, all you can do is say a prayer if your team sneaks into the postseason after a grueling 162-game campaign. If health and peak performance are on your side for a once-in-a-blue-moon playoff berth, then that’s the rare and unlikely recipe for success.

But that’s not what the Yankees are. They are the most valuable franchise in the sport. They are the most historic franchise in the sport. Yet they act like they’re helpless in a sense because they want to shirk responsibility for their poor decisions and they don’t want to go above and beyond with their spending like the Dodgers and Mets do. Is spending more money the answer every time? No. But it is if you’re a piece or two away from the ultimate goal.

And that’s been the exact story of the Yankees, especially under manager Aaron Boone. There’s always something missing. Whether it’s a top-heavy roster constructed like a Jenga tower or a lineup of guys who lack a killer instinct when October arrives, they’ve gotten crushed by equal or superior opponents on the biggest stage. Each year, fans have gotten the same dose of nonsense as to why.

But the jig is up. The Yankees are officially wrong about their take on the playoffs. Getting outclassed over and over again can no longer be disguised as “bad luck.” The Yankees just don’t have what it takes under this current regime. Since 2010, they have the same number of World Series appearances as the Detroit Tigers, New York Mets, Chicago Cubs, Cleveland Guardians, Washington Nationals, Atlanta Braves, Tampa Bay Rays, Philadelphia Phillies, and Arizona Diamondbacks. The Blue Jays just joined that list after finishing dead last in the AL East last year. All of the Boston Red Sox, Texas Rangers, San Franisco Giants, St. Louis Cardinals, Kansas City Royals, Houston Astros and LA Dodgers have more appearances. In fact, the Dodgers have five appearances in the last nine years. They are what the Yankees think they are. Meanwhile, the Boone/Cashman Yankees are officially living in the past when referencing their success. It’s been 16 years since their last title. It is the second-longest drought in franchise history (1979-1995).

The Yankees have put themselves in the category of the teams who are incapable of taking sustained playoff success to the next level. Over that same span, alongside the other teams with just one World Series appearance, the Yankees have made the playoffs 12 times (the most of that group). Better teams have used their past playoff failures and built off them, leveraging their experience at some point down the road.

Not New York. They win one pennant, get destroyed in the World Series, and ask the fans why they’re unhappy after the result. They got pasted by the Red Sox and Astros over and over again and didn’t learn from it. Outside of their Wild Card victory over the Red Sox in 2025, the Yankees only defeated the Twins, Guardians, Royals, Orioles and Athletics in the postseason since 2010.

They cut payroll after trading for Giancarlo Stanton. They didn’t pay an ace until Gerrit Cole in 2020. They were ready to risk losing Aaron Judge when they lowballed him prior to Opening Day in 2022 with a weak contract offer he requested it not get leaked to the media (and it did). They’ve let the Dodgers take countless free agents from them, which has resulted in LA building a dynasty while the Yankees are experiencing excessive roster turnover for the fifth straight year.

The Yankees have built marketing stability. They are consistently relevant. They remain an omnipresent brand. They print money. That’s all they care about. They give us a product that’s good enough to talk about after September most of the time, but underwhelming enough to be forgotten about 1-2 weeks later. That’s easy to do when you can spend more than 75% of the league with your eyes closed.

Getting lapped by the Jays, who just went from worst-to-World Series should sound the alarm. But it won’t. The Yankees will be right in the mix for a spot in the AL playoffs in 2026, only to beef it when the next rising squad decides they want it more.