Yankees: 4 Best NYY Teams That Didn’t Win the World Series

The New York Yankees have left a few rings on the table across the decades.

The first thing a Yankees fan will likely say to any offending bystander is, of course, “27 rings!”

But, if you let us perch by your shoulder a little longer, our hardened exterior will break down, and we’ll start blubbering like any other diehard about the ones that got away.

That’s the harshest irony about fandom, right? You remember your toughest losses 100 times more vibrantly than your greatest triumphs.

Though the Yanks have objectively walked away the victor plenty of times, New York should have well more than 27 rings by now, if we’re being honest. These early exits hurt the most.

4. 2002 Yankees

Somehow, the 2002 Yankees fell early to the eventual World Champion Angels.

The 2002 Yankees had it all — especially pedigree, considering they were a largely improved version of the team that had gone to four consecutive World Series.

Though the Yanks had lost luminaries like Tino Martinez, Scott Brosius, and Paul O’Neill (and to be fair, those are some big ol’ guns), the roster was reinforced in all the right places.

34-year-old Robin Ventura posted an All-Star season at third in Brosius’ stead, socking 27 homers. Jason Giambi took over at first, and put up his greatest season in pinstripes (ever?), slashing .314/.435/.598 and bashing 41 homers and 122 RBI.

Though an outfield trio of Shane Spencer, Rondell White, and Raul Mondesi couldn’t quite approximate O’Neill, Alfonso Soriano made The Leap, hitting .300 with 39 homers.

In response to the changes, New York went 103-58, adding eight wins to the previous campaign. Of course, it all…came down…to the pitching. Mike Mussina and Roger Clemens regressed, and were only slightly better than league average (109 and 102 ERA+, respectively). Though Andy Pettitte and Orlando Hernandez were stellar, and Ted Lilly filled in the gaps to perfection, the rotation struggled to contain the Angels in prime time.

New York took Game 1 of the ALDS 8-5, but stunningly lost the next three contests 8-6, 9-6, and 9-5. It’s rare that a supreme slugging team gets into four straight slugfests in October and loses three consecutive. Odds would’ve leaned towards this being a 2-2 series heading back to the Bronx. Instead, Pettitte, Mussina, and Wells all lost their starts, Hernandez cratered in relief, and we didn’t get Washburn-Clemens in a Game 5 rematch. We got nothin’.

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Recency bias? Sure. Also, the 2019 Yankees withstood every possible injury, still won 103 games, and had the mojo of a champion.

Surely, you envisioned this team winning the World Series a few different times during the season. Perhaps when Brett Gardner and Mike Ford went back-to-back to stun the A’s, you turned to your buddy with a glint in your eye.

Maybe when they mounted a stunning comeback to sweep the Red Sox in London, you called your dad and dared to dream. And when Masahiro Tanaka walked off the mound in Houston in Game 1 of the ALCS, you definitely let optimism become overconfidence.

Duh. Of course you did. This team had it.

Alas, when they ran into the mountain that’s blocked them repeatedly throughout this new era of Yankees baseball, the final frontier, they fell victim once again to, ahem, heightened technology.

The worst part of this gut punch will always be its lingering illegitimacy. In 2017, when the Yankees lost a World Series berth in similar fashion, it became clear the next week that that scrappy team would’ve been outclassed by the Dodgers, who simply had more fighters at every turn.

In 2019? The Yankees were better than the Astros, point blank, and then a devastating slate of Recent Yankees Playoff Stuff befell them right at the precipice. Clutch hitting disappeared, the last pitcher on the roster faltered, and we went home empty-handed yet again.

But we shouldn’t have. And you know it.

1. 1994 Yankees

The 1994 Yankees should’ve been Don Mattingly’s ticket to the World Series.

The 1994 Yankees are the only team on this list that exists in no man’s land. The others tried, and failed, to win a World Series. The ’94 Yanks never got to try, and will forever exist in a box like Schrodinger’s Cat.

While the work stoppage may have hurt the fans of Montreal more — after all, they lost their franchise in its wake — New York lost the second-to-last chance of Don Mattingly’s career to extend him into postseason play, and they were absolutely dominant, sitting at 70-43.

This offense was merciless — Wade Boggs hit .342, Paul O’Neill hit .359, and Mike Stanley hit an even .300 with 17 bombs from behind the plate. Mattingly slashed .304/.397/.411 — his trademark power was gone, but the man could still wake up and hit .300, if his back allowed.

Would the rotation have held up? Jimmy Key was 17-4 with a 3.27 mark, a bonafide ace. Scott Kamieniecki also had an ERA under 4.00, and would’ve been your Game 2 starter. Melido Perez posted a 4.10, Jim Abbott a 4.55, and Terry Mulholland was totally useless, but…they had Games 1-3 relatively settled, along with a nails closer in Steve Howe.

The bottom line here? I can conclude anything about the 1994 Yanks. You’ll never know. And since they’re the only option on this list without a defined conclusion, I can safely say they’re the best bet for World Series speculation. After all, they never lost one, and they absolutely bashed. It’s a shame we didn’t get to finish following the journey.