How the Yankees Became Baseball’s Most Improbable Underdogs

The Red Sox’s ALDS victory completes the archrivals’ role reversal.

The Boston Red Sox second baseman Brock Holt (12) celebrates hitting a two-run home run in front of the New York Yankees catcher Gary Sanchez (24) during the ninth inning in Game Three of the 2018 ALDS playoff baseball series at Yankee Stadium. Holt became the first player in postseason history to hit for the cycle. (Adam Hunger / USA TODAY Sports / Reuters)

Bucky Dent threw out the first pitch. Aaron Boone assumed his managerial perch in the home-team dugout. And in an agonizing ninth inning—as Craig Kimbrel hunched over the mound, the New York Yankees loaded the bases, and fans watched breathlessly—Babe Ruth seemed to wink at the Red Sox from his plaque in Monument Park.

But try as they might, the ghosts of Octobers past didn’t haunt the Red Sox on Tuesday.

It took four games for the Sox to put away the Yankees, and despite a less-than-dominant start in Games One and Two at home, Boston punched its ticket to the American League Championship Series in the same fitting place it clinched this year’s divisional title: the Bronx.

It would have been impossible for the drama of the Yankees–Red Sox series to live up to the hype, in part, perhaps, because the nexus of power within the rivalry has shifted. The American League East juggernauts hadn’t squared off in the playoffs since 2004, when an immortal, raucous band of self-proclaimed “idiots” propelled their shaggy-haired, whiskey-swigging selves to the greatest comeback in Major League Baseball postseason history. And in the 14 years since, the Red Sox not only have “reversed the curse,” but have also reversed the narrative altogether. With three World Series titles, three straight division titles since 2016, and a fan base as expectant as ever, the Red Sox have managed to do the near impossible: turn their rivals, the most successful franchise in baseball, into something of an underdog.

The plot of the 2004 American League Championship Series—during which the Red Sox overcame a three-game deficit to vanquish the archrival Yankees and win their first World Series in 86 years—is so cinematic, it’s practically unbelievable. No one who played in that epic series is still on the field, and many of 2004’s most famous faces have settled into new identities altogether: Derek Jeter the owner; Alex Rodriguez the studio darling; David Ortiz the de facto mayor of Boston. But despite how far removed that series of 14 years ago seems, its legacy looms large over the East Coast rivals, particularly during a season when the intensity of the teams’ relationship reached a fever pitch.

Of course the Yankees, with their 27 World Series titles, $4 billion valuation, and interminable pinstripe swagger, will never be a true Cinderella story. But it’s been nine seasons since the Bronx Bombers last hoisted the Commissioner’s Trophy, and while many fan bases scoff at calling that stretch a drought (sorry, Milwaukee), it’s an eternity in New York.

A quick Google search of underdog turns up words and phrases like humble, long shot, and dark horse. It’s laughable to attach any of these monikers to the contemporary Yankees, whose roster boasts talent in spades. With Aaron Judge and Giancarlo Stanton in the lineup, Aroldis Chapman in the bull pen, and tens of millions of dollars in the bank, the Yankees are stacked for years to come. But high-profile people regularly default to calling themselves underdogs long after they’ve reached the apexes of their fields. Being the underdog is appealing because there’s romance in an improbable, hard-fought victory. And as several psychological studies have concluded, people love to root for a presumed loser. Could the franchise non-ironically referred to as the “Evil Empire” ever take up that mantle? And, more important, would such a historically confident team even want to?

Perhaps not, especially within the broader Major League landscape, populated by teams like the San Diego Padres and the Miami Marlins. But in comparison to their archrivals, there may be hope yet for the glitzy and glamorous Yankees to engender some underdog goodwill. Since the Yankees last won the World Series, in 2009, they’ve been about even with the Red Sox, besting Boston 85 times in the past nine regular seasons and falling to the team 83 times. But unlike the Red Sox, who won the World Series in 2013, the Yankees have left October empty-handed ever since. New York hasn’t even made it past the ALCS this decade, and it hasn’t topped the division since 2012. The fan base is hungry for the Yankees’ 28th title, and the so-called Baby Bombers are under pressure to deliver.

The Red Sox, meanwhile, started the 2018 season with an incredible 17–2 record and finished it with a league-leading 108 wins. But it’s not just the outstanding on-field performance that suggests a shift in the Yankees–Red Sox dynamic. It’s the attitude, too.

While the Yankees are far from the debauchery and goofiness of the 2004 Red Sox—the team is, after all, still devoid of anyone sporting Johnny Damon–style hair and antics—Boston has made some New York moves lately. Not only did the Red Sox tout the highest payroll in Major League Baseball this season, but the owner John Henry’s decision to fire the manager, John Farrell, at the end of the 2017 season reads like a page out of George Steinbrenner’s playbook. Farrell shepherded the Sox through a tumultuous five years that included a championship ring and two straight finishes in the basement of the AL East. But the skipper seemed to right the ship after 2015, and the Red Sox reclaimed the divisional title in 2016 and 2017. Yet the squad exited early from the playoffs both years, so Farrell had to be replaced. The ouster is a quintessentially New York move. So much so that the Yankees, too, let their manager go after a 90-plus win in 2017.

Though he had an elite crop of relievers at the ready this week, the Yankee manager Aaron Boone left his starting pitchers in too long in Games Three and Four of the American League Division Series against the Red Sox. There’s no way to know if doing so cost his team the series, but it certainly didn’t help. The former Sox skipper Grady Little made the same mistake in Game Seven of the 2003 American League Championship Series, and Boone’s bat doled out punishment for it. This time, however, the Red Sox didn’t need walk-off heroics to finish off their rivals. They’ll face the Houston Astros at Fenway Park on Saturday, while their underdog foes are forced to wait for winter to thaw.

All that’s left for the Yankees is the disappointed refrain of the reluctant optimist: There’s always next year.