The Yankees Season That Still Haunts Fans: Uncover the Untold Story Behind the Frustration

Spring training is just around the corner—only a week until the Yankees’ pitchers and catchers hit the field, and I can hardly wait. It’s that bittersweet spot in the calendar where the excitement builds but the action hasn’t quite started, leaving us plenty of time to reflect on the franchise’s history filled with both glory and gut-wrenching disappointments. Sure, the Yankees boast a staggering 27 championships, but their journey has been punctuated by seasons that stopped just short of their ultimate goal, leaving fans holding their breath and clutching memories of what could’ve been. From the heartbreak of ’60’s sudden World Series loss to the uncanny collapses in ’85 and those seismic moments in the early 2000s, New York’s baseball saga is nothing if not dramatic. Each era tells its own tale of near-misses and wrenching defeats—like the mystifying 1994 season cut short by a labor dispute, or the infamous postseason losses that haunt the Boone years. Today, I want to delve into those near-misses and resonate with the emotions that any true Yankees fan knows all too well. Plus, we’ve got an intriguing debate brewing around the current bullpen—optimism polarizing with skepticism—and some fascinating profiles on players past and present to keep the pulse of this beloved team beating strong. Ready to relive the triumphs and the stumbles, and maybe spot some hints for what’s ahead? Let’s jump right in. LEARN MORE

Welcome to Wednesday. The Yankees’ pitchers and catchers will officially report to spring training a week from today! Hurrah. There’s not much else going on though, so we’ll get into today’s discussion prompt.

The Yankees have won 27 championships of course, but there have still been plenty of seasons that ended with frustrating results. Here’s just a smattering that come to mind:

The 1960 Yanks bludgeoned the Pirates in the World Series in terms of run differential; it didn’t matter when they lost in seven games on Bill Mazeroski’s walk-off bomb.
Prior to their long playoff drought, the 1980 and 1981 Yanks saw their seasons ended by two postseason opponents from the previous decade who flipped the script (the Royals and Dodgers).
The 1985 Yanks won 97 games in Don Mattingly’s MVP season and Rickey Henderson’s superb New York debut, but missed the playoffs since the Wild Card did not yet exist and Toronto beat them out for the AL East.
No AL team had a better record in mid-August of 1994 than the ascendant Yankees. A labor dispute cut the season short on August 11th and the World Series was cancelled. Fans never got to know if this Mattingly team would have gotten him to that Fall Classic.
The Yanks did return to the playoffs at last in 1995, but after jumping out to a 2-0 series lead over the Mariners, they lost three in a row in Seattle to get eliminated with Edgar Martinez delivering a dagger of a double for the final walk-off blow. David Cone still curses the Kingdome.
Can one really complain after a three-peat dynasty finally ends in 2001? Well, despite some downright thrilling playoff heroics in wake of 9/11, it did end in brutal fashion thanks to a shocking Mariano Rivera blown save that featured bad defense, an inexplicable Tony Womack double, and Luis Gonzalez winning the World Series for Arizona on a bloop to shortstop with the infield in.
The 2003 Yanks might have been the best team in franchise history to not win a World Series. They won a playoff series for the ages too, as an ALCS Game 7 rally off Pedro Martinez and Aaron Boone’s walk-off homer created an all-time moment. Instead of riding that wave to a championship, they got clowned by the Marlins of all teams in a six-game World Series loss that ended in Josh Beckett’s Yankee Stadium shutout.
2004. There have been 10,000 sports documentaries about this one, and they’re still being churned out. NEXT.
Although the Yankees had four deeply frustrating first-round exits during the first decade of this century, 2006 might take the cake. The Tigers had stumbled badly down the stretch to squander their 10-game AL Central lead and fall into a Wild Card spot. The Yankees were “Murderers’ Row and Canó,” in the words of Detroit skipper Jim Leyland. Guess which one of these teams fell apart in the ALDS?
The Yankees’ post-Derek Jeter youth movement hit the jackpot in 2017 with rookie Aaron Judge suddenly turning into a 50-homer MVP candidate. This popular team went from low preseason expectations all the way to Game 7 of the ALCS, which they lost to an Astros club that soon became infamous.
Take your pick from the Aaron Boone Era. 2019, when the 103-win “Next Man Up” Yanks went down in the flames to the Astros in the ALCS again, this time in Jose Altuve walk-off fashion? 2022, when another ALCS rematch with Houston ended in a thoroughly uncompetitive sweep? Or perhaps 2024, when one year of Juan Soto got New York back to the Fall Classic, but a previously supernova Judge went cold in October and the World Series against the Dodgers was lost with questionable managing and awful Game 5 defense?

The contenders are fierce. My old colleague Greg Kirkland always pointed to ’94 due to never getting to find out the true ending for what that team deserved. I was too young for that, but I think that’s entirely fair. Among the teams I watched most closely, 2001 was the most heartbreaking and 2004 the most embarrassing — though boy did the very end of 2024 give that a run for its money. What about you?

Today on the site, we’ll have two particular articles that will work in tandem with each other about a contentious topic at the moment: the Yankees’ bullpen. Andrés will take the optimistic view and argue why this group is being overlooked and could turn out to be quite good, while Jeff will be the opposition and detail why it’s a point of weakness at the moment that should have been improved. Elsewhere, we’ll have our Peter celebrate a forgotten
“Lefty” from Yankees history for our Birthdays series, and Nick will be on double duty for a season preview post on Paul Blackburn and a look book at Andy Pettitte’s shocking-but-welcome unretirement in spring 2012 as part of our 50 Most Notable Yankees Free Agents.