When the 1990s began, the Yankees were a bit of a joke. They had fallen from back-to-back World Series champions in the late-‘70s to mere title-less contenders in the mid-’80s, and by the end of that decade, they were a sub-.500 team. Their bombastic owner was about to be suspended from baseball for conspiring to dig up dirt on his own superstar, and there really weren’t many compelling players on the roster.
By the time the 1990s ended, the Yankees had won their third World Series crown in four years. They had an explosive core of young talent led by multiple Hall of Famers and annual All-Stars, and the more experienced players who joined them combined to create the game’s most dominant dynasty in more than a generation. That bombastic owner was back again, but at the very least, he was a little easier to keep in check, given all the success.
Most importantly, those Yankees showed no signs of slowing down. They were just going to keep winning until their rivals altered their tactics. Sure enough, the Major League Baseball that fans witnessed on a regular basis 25 years ago looks different than the version played today. Teams adapted to try to beat those dynasty Yankees, effectively changing the game as we know it.
The league first learned its lesson against that generation of Bombers in 1996. The Braves were the class of baseball, defending World Series champions and winners of two other recent National League pennants as well. Although the Yankees had worked hard to return to the World Series for the first time in 15 years, they were not expected to win and indeed, they fell into an 0-2 hole. Tasked with trying to survive on the road in Atlanta, they thrived.
A remarkable blend of youth and veteran tenacity sent the Fall Classic back to Yankee Stadium, where the Yankees officially unseated the Braves as champions in Game 6. The Bronx erupted, and although New York failed to repeat in ‘97, they rebounded with a vengeance in ‘98 in a preposterous 125-win campaign. They bulldozed their way to another title with one of the greatest MLB campaigns ever seen, and for good measure, they won it again in ‘99 by sweeping Atlanta away. Then in 2000, they knocked out the Mets in the Subway Series to complete MLB’s first “three-peat” in 26 years.
Derek Jeter. Mariano Rivera. Bernie Williams. Jorge Posada. Andy Pettitte. Roger Clemens. Tino Martinez. Paul O’Neill. Scott Brosius. While a few names had departed around the time of the new millennium, all of these guys were still around and productive, and that’s to say nothing of the many other useful players on the team. The not-so-subtle recipe developed in the Bronx involved making nearly every spot on the roster a productive one, whether it was an October force like Orlando “El Duque” Hernández, a reliable bullpen lefty like Mike Stanton, or a savvy Trade Deadline addition like 2000 David Justice.
Most concerning for the other 29 MLB teams was that owner George Steinbrenner had both the financial capital and the ambition to keep the best players in pinstripes and add more into the fold. By the early-2000s, Jeter, Rivera, Williams, and Posada had all been extended; none would ever play a game with any other team. Complacency led to Pettitte’s three-year sojourn to Houston in the mid-2000s, but he ended up returning for six more seasons and another championship. The Yankees also opened the free agent coffers for future Hall of Famer Mike Mussina, 2000 AL MVP Jason Giambi, and Japanese slugger Hideki Matsui before pulling off a stunning trade for a near-incomparable talent — and at the time, a near-incomparable contract — in Alex Rodriguez.
By the time the Yankees had actually acquired A-Rod though, the rest of the league had begun to fight back.
On the field, progress had been made. The Yankees came oh-so-close to a fourth-straight World Series title in 2001 before Arizona crushed their dreams in the ninth inning of Game 7. A pesky Angels team shocked the baseball world by dispatching the Yankees in a four-game ALDS in 2002, and though Aaron Boone’s homer prolonged Boston’s infamous “Curse of the Bambino” in 2003, the Marlins pulled off a Fall Classic upset by winning in six.
But it was off the field where the tides had really begun to turn. The league assembled a Blue Ribbon Committee to release a report in 2000 on the sport’s economics, and it wasn’t exactly a secret that MLB leaders wanted to find a way to penalize spending. This was, of course, in the interest of the vast majority of owners, who were more cheap than Steinbrenner and did not want to invest nearly as much in the product. Still, the Committee encouraged changes that led to comparatively more strict luxury tax penalties, which would be partially distributed to smaller market teams. The Yankees were hit by the tax every year for the rest of Steinbrenner’s life; only three other clubs paid it even once during that span (2003-10).
The Yankees’ dynasty also motivated teams to rethink their entire modus operandi. Technology was rapidly expanding and there were better methods of conducting player evaluation than there were even a decade prior. The same ol’ strategies could no longer be safely relied upon to beat the Bombers. Some had already taken steps in this direction, most famously the Moneyball Oakland A’s, who actually won more regular season games than the Yankees from 2000-03 despite a much lower payroll. Oakland wasn’t the only team in the sport doing all this, but their coverage brought the most attention to the idea.
Although those A’s might have run into trouble in the playoffs, outside executives understood what their success meant. If they were savvy enough in their baseball operations, then they could find a way to remain competitive with New York no matter how much Steinbrenner spent. The owners themselves also realized that they could simply spend less on their product and make big on-field profits, which obviously provided ample motivation, too.
So numerous MLB front offices reformed over the course of the 2000s. Internal systems throughout the game improved. To be clear, the Yankees also eventually evolved with the times (and endured mistakes in free agency as well) and beefed up their analytics department, but with so many other teams doing the same, it all amounted to keeping pace — regardless of how many analysts they hired.
Playoff success can sometimes be random, but the results speak for themselves. All of the following 10 teams have appeared in multiple World Series over the last 20 seasons:
The Yankees have made it into just one, 2009, which was the last gasp of their ‘90s core combined with a legendary A-Rod hot streak and an unusually talented prime free agent haul in the previous offseason.
It’s also hardly a coincidence that MLB has not seen a back-to-back champion since those dynasty Yankees. Each of the other major American sports leagues has had at least one repeat, but only the 2008-09 Phillies even managed to make it back to the World Series the year after winning it all, and they lost. The 2010-14 Giants won three championships in five seasons, but needed breather years (for lack of a better term) between each title where they missed the playoffs entirely. So many MLB teams have front offices comprised of extremely smart people, thus leading to an extremely competitive sport — even with some organizations tanking at times.
Who knows? Maybe the 2023 Astros shake off their recent sweep at the hands of a suddenly-rebuilding Yankees club, go on a run, and break the trend to repeat as World Series champions. Even with a subpar season to date by their standards, it would not stun anyone in the industry whatsoever. Hell, the 2000 Yankees were a worse team and much like these Astros, they were accustomed enough to postseason glory that come October, they found a second gear. With four pennants in six years now, Houston is simply used to winning as well.
Until that time, however — and honestly, until someone else manages to “three-peat” — no modern MLB team can say that they changed the game like the ‘90s Yankees dynasty.