Skip to main content

Yankees' latest playoff disaster shares eerie similarities with Phillies' fate

Misery loves company.
ByEthan Williams
Oct 7, 2026; Bronx, New York, USA; New York Yankees injured right fielder Aaron Judge (99) watches from the dugout during the second inning of game three of the ALDS against the Tampa Bay Rays during the 2026 MLB Playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images
Oct 7, 2026; Bronx, New York, USA; New York Yankees injured right fielder Aaron Judge (99) watches from the dugout during the second inning of game three of the ALDS against the Tampa Bay Rays during the 2026 MLB Playoffs at Yankee Stadium. Mandatory Credit: Brad Penner-Imagn Images | IMAGN IMAGES via Reuters Connect

The New York Yankees’ season came to an end on Wednesday night, less than a week after that of the Philadelphia Phillies. Many fans of the Bronx Bombers are ready to burn down Yankee Stadium, viewing their beloved team as an aging, overpaid mess that simply isn’t good enough to win a World Series. Where have Phillies fans heard that before?

The similarities between the Phillies and Yankees run deep. New York’s $348 million luxury tax payroll sits second in all of baseball, just $13 million ahead of the Phillies in third place (both well behind the evil empire Los Angeles Dodgers). The Yanks employ five different players who each have an average annual value of more than $25 million per year, some of whom are making substantially more than that. The Phils are in an identical boat with five of their own (not including Aaron Nola who sits at $24.5 million).

The top-heavy nature of both rosters has made it difficult to backfill trouble spots with mid-tier players, but both clubs have tried anyway. The Yankees had Ryan McMahon, Jazz Chisholm Jr., Trent Grisham and others earning eight-figure salaries while providing less-than-star-level production this year. The Phillies had their own version of this, as J.T. Realmuto, Alec Bohm, Brad Keller, Adolis García and more were paid handsomely to not contribute.

One major difference between the two clubs has been player development. While Yankees stars Aaron Judge, Giancarlo Stanton and Gerrit Cole dealt with injuries this season, the team was buoyed by youngsters Ben Rice and Cam Schlittler, the former having crushed 41 homers and the latter the odds-on favorite to win the American League Cy Young Award.

Conversely, the Phillies had to get practically all of their offensive production out of aging veterans Bryce Harper and Kyle Schwarber, while homegrown pieces Bryson Stott, Alec Bohm and Justin Crawford have failed to develop into difference-makers at the major league level. That lack of impact talent coming through the pipeline is part of why the Phillies have devolved into an expensive morass of lengthy contracts.

And yet, the Yankees have some developmental failures of their own. Anthony Volpe was hailed as the shortstop of the future, but found himself demoted to Triple-A twice this year. Jasson Domínguez’s loud tools led to him being considered “The Martian” as a teenager, but he’s posted a sub-.700 OPS in parts of four big league seasons. 26-year-old catcher Austin Wells went from being a roughly-league-average bat to bottoming out with a .624 OPS in 122 games this season. 

The Yankees’ inability to properly surround stars like Judge, Rice, Schlittler and Cole with quality role players led to a predictable early playoff exit while Judge sat on the shelf this year. Similarly, the Phillies have bowed out earlier than expected for four straight seasons, largely due to the fact that Harper and Schwarber were not given a decent enough supporting cast to put runs on the board for a dominant starting rotation. 

Both the Phillies and Yankees are looking at difficult paths to a World Series title

If the Phillies want to finally get over the hump in October, they’ll have to spend their way out of this mess, or come up with some pretty creative trades. The team’s 29th-ranked farm system simply doesn’t have enough impactful prospects to augment a major league team that’s already starting to bottom out. The Yankees aren’t much better off, but they at least have well-regarded pitching prospects Carlos Lagrange, Elmer Rodríguez and Ben Hess on the cusp of the major leagues, as well as potential offensive forces Dax Kilby and Yostin Peña well below; George Lombard Jr. also performed nicely after an August promotion. 

And then there are the front offices themselves. Many Phillies fans are unhappy with president of baseball operations Dave Dombrowski, who’s been in power since the 2020-2021 offseason. Throughout his six years at the helm, Dombrowski has had mixed results spending big on free agent acquisitions while remaining committed to the same core that reached the World Series back in 2022. Fans that are desperate for change are setting themselves up for disappointment, as the 70-year-old will most likely receive another contract extension this winter. 

If Phillies fans think they need new blood, all they have to do is look at the Bronx where general manager Brian Cashman has been running the show since 1998. Over the course of almost three decades, Cashman has brought home four championships and three other pennants, but the last trophy came back in 2009. For a fanbase with “World Series or bust” expectations, that’s simply not good enough. No wonder both teams feel so stale.

All told, the Phillies and Yankees find themselves in remarkably similar situations this winter. Aging, overpaid rosters have failed to deliver a championship to fanbases that expect nothing less. Both cores are living off of World Series appearances from a few years ago, but have been taking steps backward since then. A pair of well-established shot callers will need to get very creative if they want to finally seal the deal, but how they'll be able to do that is anyone’s guess.

Add us as a preferred source on Google

Loading recommendations... Please wait while we load personalized content recommendations