The Boston Red Sox second baseman Ian Kinsler (5) and shortstop Xander Bogaerts (2) celebrate after defeating the Houston Astros in Game Five of the 2018 ALCS playoff baseball series at Minute Maid Park.Troy Taormina / USA TODAY Sports / Reuters

Fenway Park was euphoric.

The Red Sox may have lumbered through the game’s first seven innings and found themselves in a five-run hole in the bottom of the eighth, but suddenly the team’s bats came alive. Out of nowhere, Christian Vazquez was hustling as fast as his catcher’s legs could take him toward home, narrowly shimmying around a tag at the plate to tie the game. And then a long fly ball was crashing into the Green Monster’s scoreboard, and Mookie Betts was rounding third to give the Sox the lead and, later, the victory.

It was exhilarating. It was triumphant. It was the feeling that inspires normally levelheaded people to throw on tattered baseball caps and declare a lifelong allegiance to a ball club.

It was also April.

The 2018 Red Sox—whose record improved to 8–1 on April 8 and who will face off against the Los Angeles Dodgers on Tuesday in Game One of the World Series—were still in their infancy. But it would have been impossible to intuit the relative irrelevance of that particular game from the intensity that cloaked Fenway Park that day. There may have been 153 games left to play during the regular season, but as “Dirty Water” blared over the loudspeakers and jubilant fans poured out onto Lansdowne Street at the end of that brisk Sunday contest, the expectation in Boston was already clear: For this team, anything but a World Series ring would be a failure.

Though the Red Sox dropped their Opening Day contest, they never flew under the radar. The team announced its dominance early, winning 17 of its first 19 games during a blazing hot streak that would set the tone for an elite ball club’s outstanding year. By the time the sun set on the 2018 slate of regular-season games, Betts, Jackie Bradley Jr., and company had won a league-leading 108 contests. No team has finished the regular season with a better record this millennium since the 2001 Seattle Mariners won a staggering 116 games. But as the Mariners, who fell to the Yankees in that year’s ALCS, learned, all those regular-season wins don’t matter in October, and especially not in Boston.

For a city of its size, Boston consistently punches above its weight. Not only does it host several of the nation’s top colleges and universities, but it’s also home to some of the country’s best hospitals and a technology sector poised to give Silicon Valley a run for its money. Still, for the past two decades, nowhere has Boston’s presence been more outsize than in the athletic arena. The Hub has arguably been the most dominant American sports city of this millennium, and the competition isn’t even close.

Since Tom Brady, then 24 years old, hoisted the Lombardi Trophy over his head for the first time in February 2002, Boston’s four major sports teams have won nine titles. The Celtics, the Bruins, the Patriots, and the Red Sox all made the playoffs in each of the past two seasons, a feat no other city’s teams can lay claim to. In fact, the last time all four of Boston’s major sports teams were locked out of the postseason was in 2000, after the Patriots coach Bill Belichick’s inaugural year as New England’s leader.

But expectations undeniably follow repeated success, and all the victory parades have stoked a feeling among some Boston fans that an entire season is a wash if it doesn’t end in confetti. Such an attitude is particularly onerous in baseball, where the 162-game regular season seems designed to identify the most well-rounded and successful team. Whereas in sports like college football, in which the thrill of an upset victory over a superior rival can sustain a fan base for an entire disappointing season, baseball’s glorious slog ensures that it’s only the stars of the postseason that ever get remembered. And winning the regular season has been far from a harbinger of World Series titles: In the 23 seasons since Major League Baseball introduced the Wild Card, the team with the outright best regular-season record has won the championship just five times. Such a historical precedent doesn’t exactly inspire confidence in this season’s Red Sox.

The Fenway faithful are far from the only contingent of fans to believe that unless their team finishes first, it may as well have finished last. Perennial contenders like the contemporary Los Angeles Dodgers, the Golden State Warriors, and the Pittsburgh Penguins foment the same expectations, because a playoff berth has become their status quo. But while a glistening stretch of sustained success should be heralded by coaches, fans, and players, if it doesn’t include a ring, those memories can be tinged with regret. Take the Atlanta Braves, who won the National League East every single season from 1995 to 2005 but came away with just one World Series trophy. John Smoltz, who pitched for Atlanta during this stretch, told ESPN in 2016 that he still believes that the team should have achieved more in the postseason. The Braves were dominant, but they weren’t a dynasty.

Sustained success, however, isn’t the only reason organizations feel the pressure to win it all or call it a wash. The Washington Nationals, for instance, flirted with .500 play all year and drastically underperformed in 2018. The record alone may have been enough to irk a fan base that has watched its team lose in the NLDS four times since 2012, but this year felt pressing for another reason: Bryce Harper, whose contract with the Nationals is expiring. Harper, who has been the face of the franchise since his 2012 debut, may no longer be a fixture of the District come spring. And so while the Nationals are far from seasoned winners like the Red Sox, the notion that this year had better be the year was weighty all the same.

As Nationals fans steel themselves to say goodbye to their leader, Red Sox fans stare down their first World Series of the post–David Ortiz era. With a slate of talented young players such as 21-year-old Rafael Devers, who hit a three-run blast in Game Five of the ALCS, the Red Sox appear poised to remain in the playoff conversation for years to come. But the prospect of a sunny future certainly doesn’t mitigate the pressure to win now. Elsewhere, baseball fans may roll their eyes at yet another deep run for the Sox, but Bostonians are reveling in their team’s postseason glory and will continue to do so—unless, of course, the Sox choke. Then the off-season will be filled with bitter disappointment and the insatiable push to try again.

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