If this debate was ten years ago, my answer to the question of who the most hated team in baseball was would definitively have been the New York Yankees.
The Bronx Bombers of the last 20 years have represented everything about baseball that I despise. Rather than go about winning championships through development of talent, hard work, and long-term strategy, the Yankees would allow other franchises to do all the dirty work. Then, right when all of that hard work by “lesser” franchises was about to pay off because one of their athletes had established himself as a true superstar, the Yankees would swoop in, price almost every other team in the league out of the market for that player (including the very team that had invested so much into his development), and simply acquire an already cultivated superstar.
Admittedly, part of my resentment stems from the fact that the strategy works. From 1996 until 2000 the Yankees pulled off an impressive FOUR World Series championships. George Steinbrenner had monopolized the game of baseball, and it took all of the fun out of the game for fans anywhere else in the country.
Leading the charge for the anti-Yankees bandwagon was the Boston Red Sox, their bitter rivals, whom many had perceived as the yin to the Yankees’ yang. While the Yankees had gone on to purchase one World Series after another, the Red Sox were in the throes of an 80+ year World Series Championship drought. For all of the reasons that the Yankees were despised, the Red Sox loved.
Compounding the pro-Red Sox support was the fact that they, just like every other team in the Majors, fell prey to the big-budget mentality of George Steinbrenner and had to sit back while once revered players from Fenway celebrated World Series championships in pinstripes. Even Red Sox stalwarts like Wade Boggs and Roger Clemens ultimately wound up defecting to the Dark Side, WILLINGLY signing contracts in New York later in their careers, and were perceived by many as having sold their soul for a World Series ring.
Then the Red Sox changed. Like so many of the players that Red Sox fans (and those who vicariously supported Boston through a shared hatred of the Yankees) cursed for having sold out just for the prospect of a World Series championship, the Red Sox themselves hypocritically became sellouts. Under the philosophy of “In order to BEAT the Yankees, we must BECOME the Yankees,” guys like Theo Epstein and Mike Port began to seek out and steal the high-priced talent in the league for themselves, taking players away from other teams… even that team in New York.
Since 2000 the Red Sox have bought talent like David Ortiz, Manny Ramirez, Kevin Millar, and Curt Schilling. They have overpaid in bidding wars for guys like Eric Gagne, and have dropped $50M just to reserve the rights to TALK to Daisuke Matsuzaka. Basically, they had become the very thing that they once hated.
In fairness, this new strategy has worked for them, which makes their treachery that much worse! Like the Yankees of the late 1990s, the Red Sox have since won multiple World Series championships, and are now perennial postseason contenders in the AL East (although this year has been anything but a success for Boston thus far). However, that success came at the price of their principles. For the very reason that they once berated the Yankees, they now are guilty of committing the same infractions.
Once perceived as bitter rivals, the New York Yankees almost became role models to the Red Sox, as they graduated Valedictorians from the “George Steinbrenner School of Winning in Baseball.”
The Boston Red Sox are the most despised team in baseball today because they not only bought (rather than earned) their way into the forefront of MLB competition, but more importantly, they did so in hypocritical contrast to all that they once stood against.
At least the Yankees come by it honestly.