It took a conversation about the New York Yankees’ retired numbers for me to realize that our fanbase is a bit too caught up in 1990s nostalgia.
The conversation was with my brother, a Phillies fan. While my brother was vaguely aware that the Yankees have retired a lot of numbers, he was surprised when he saw some of the specific names on the list.
The Yankees and Phillies have different philosophies about which numbers should be retired. While the Yankees will consider retiring the number of anyone who could be described as a franchise “legend,” the Phillies (mostly) reserve the honor for Hall of Famers.
So, for my brother, it was surprising that the likes of Jorge Posada, Bernie Williams and Paul O’Neill had had their numbers in Monument Park. From my perspective, though, I found it slightly odd that the Phillies have not retired the numbers of Bobby Abreu, Jimmy Rollins or Chase Utley.
Yankees’ retired numbers show fanbase is stuck in the 1990s
But as I pondered this difference further, I realized it wasn’t as simple as the Phillies having a higher standard for number retirement than the Yankees do. It’s not as if the Yankees always retire the numbers of their important “lesser” stars. If that were the case, surely Tommy Henrich’s number would be retired.
Henrich, a longtime teammate of Joe DiMaggio’s, was praised as the Yankees’ unofficial team captain. He made five All-Star teams and played on five World Series-winning teams.
You could say Henrich was to Joe DiMaggio what Paul O’Neill was to Derek Jeter. And indeed, Tommy “Old Reliable” Henrich retired with a near identical Baseball Reference WAR to Paul “The Warrior” O’Neill. For that matter, he might have put up a far stronger total, if not for a little event called World War II.
So why is O’Neil’s number retired and not Henrich’s (or Willie Randolph’s? Or Graig Nettles’?, etc)? The answer is simple: O’Neill played in the 1990s.
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November 4, 2001: Diamondbacks’ Luis Gonzales singles home the winning run off Mariano Rivera in the Bottom of the 9th of Game 7 and Arizona wins the World Series over the Yankees. pic.twitter.com/0wVzNY2TgE
— This Day In Sports Clips (@TDISportsClips) November 4, 2022
The 90s were indeed a great decade for the Yankees. As O’Neill said: “Fans remember teams that win, and we won a lot!” Fair enough … but it’s not as if the 90s were the only decade in which the Yankees won championships — Henrich won just as many as that dynasty squad.
Perhaps it comes down to how different things were when O’Neill played than when Henrich did. There were only eight teams in the American League during Henrich’s career. And if the Yankees were the best of those eight teams (which they often were), they went straight to the World Series. In short, World Series wins from the 90s seem more impressive than wins from earlier decades.
Baseball changes, and Yankees fans’ expectations should too
So, modern day Yankees fans are understandably nostalgic for the 1990s. And this means great Yankees from the 90s are (possibly) overrated, relative to equivalently talented Yankees from earlier generations.
But I would argue that this 90s nostalgia causes a bigger problem for Yankees fans.
The problem I’m talking about is the expectation that the Yankees should win a World Series every year. This expectation is regularly cited by our players and fans, but it’s mocked as selfish and out-of-touch by fans of virtually every other team. In turn, it leaves us feeling utterly humiliated every time the Yankees are eliminated from the playoffs.
Yankees fans likely realize that our team will never again be quite as dominant as it was from the 1920s through the 1950s. That dominance was the product of Major League Baseball being a less developed and less competitive product.
Nonetheless, because the Yankees won an absurd four championships between 1996-2000, it’s possible for fans to hold on to the illusion that if only the Yankees found the right group of players and coaches (“real winners” like Jeter, Rivera, Pettitte, Posada, Williams, Torre and O’Neill), we could once again rack up World Series victories like they’re nothing.
The Houston Astros are World Series champions again.
— ESPN Stats & Info (@ESPNStatsInfo) November 6, 2022
They're the first franchise with a .620 win percentage and multiple titles in a six-year span since the 1953-58 Yankees. pic.twitter.com/fJocpaCt8v
We hold on to this illusion because the 90s feel like the present day. But, in fact, baseball has changed a great deal over the last two-plus decades Namely, Moneyball and the analytics revolution really only began in the 2000s.
The 90s were also the last decade before the internet took over our culture. In the 90s, it was still possible for a few well-run-teams to keep their strategies secret. In today’s world, however, information is rapidly transferred and analyzed. It would be profoundly difficult for one single baseball team to truly outsmart and overwhelm all of their rivals. While the 90s Yankees World Series run ended in 2001, it was arguably the emergence of the Tampa Bay Rays in 2008 as one of baseball’s most analytically-savvy teams that truly ended New York’s dominant reign.
I’m proud to be a fan of a team that honors its history. And retiring the numbers of local legends, like O’Neill, is a great way to do that. But honoring history also means being aware of how this game is constantly changing. Major League Baseball is more competitive than ever. To put it mildly, the next 27 rings won’t be nearly as winnable as the first batch.

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