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    Ezra Shaw/Getty Images

    The 2018 Boston Red Sox finished the regular season 108-54, a win total only eight teams have surpassed in big league history.

    Boston is locked in an American League Division Series showdown with the archrival New York Yankees. We don’t know what its playoff fate will be.

    Here’s an intriguing question: If the Red Sox fall short of winning the Commissioner’s Trophy, where would they rank among the game’s all-time postseason chokers?

    To arrive at an answer, we checked in on the winningest squads of all time that failed to win a title. We narrowed our focus to the World Series era (which began in 1903) and considered win totals rather than winning percentage.

    While regular-season win totals informed the rankings, we considered other factors such as hype, expectations and historical context.

    We’ll begin with six teams that reached the 104-win threshold and qualified for the postseason but failed to win it all, and then we’ll look at nine more instances of great campaigns that went up in October flames.

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    David Madison/Getty Images

    The following teams all finished with 104 wins but whiffed on a championship.

    Not surprisingly, the formerly cursed Red Sox and Chicago Cubs show up (and we’ll meet the Cubbies again later).

    Worth noting: The 1909 Chicago Cubs and 1942 Brooklyn Dodgers both won 104 games and missed the playoffs. 

    Also worth noting: The 1904 New York Giants won 106 games, but there was no postseason because the Giants refused to play the Boston Americans in the World Series. Needless to say, it was a different time.

    Anyway, about those 104-win, title-less teams:

  • 1910 Chicago Cubs
  • 1946 Boston Red Sox
  • 1963 New York Yankees
  • 1988 Oakland Athletics
  • 1993 Atlanta Braves
  • 2017 Los Angeles Dodgers

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    DARREN HAUCK/Associated Press

    In 2004, the Cardinals finished 105-57 and met Boston in the World Series.

    The Red Sox were a wild-card team that had been down 3-0 to the Yankees in the American League Championship Series before it staged a historic comeback.

    The shadow of the Bambino loomed large, yet suddenly it seemed destiny was on Boston’s side.

    The Sox curse-burying sweep of the Cards in the World Series may have seemed like a foregone conclusion, but it’s easy to forget St. Louis won seven more regular-season games than Boston and employed an emerging 24-year-old star named Albert Pujols.

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    Harry Harris/Associated Press

    Jackie Robinson hit .329 with a .927 OPS and 17 steals for the 1953 Brooklyn Dodgers.

    He had broken the color barrier in 1947 and won the NL MVP in 1949, and Brooklyn had reached the World Series in each of those seasons and 1952—but had never won it.

    In 1953, the Dodgers went down 2-0 to the Yankees (who finished 99-52) in the Fall Classic.

    Brooklyn won the next two contests, but New York finished with a pair of victories to take the Big Apple-centric World Series.

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    Edward Kitch/Associated Press

    Stan “The Man” Musial paced baseball with a .357 average and .988 OPS in 1943.

    He also led the game with 220 hits, 48 doubles and 20 triples.

    Concurrently, the Red Birds flew ahead of the pack with 105 wins.

    Musial won rings with St. Louis in 1942, 1944 and 1946, so this isn’t some Ernie Banks-esque tale. And like the Dodgers, the Cardinals enjoyed enough previous and subsequent postseason success to take the sting out.

    Then again, the Cardinals’ 4-1 loss to the 98-win Yanks was a noteworthy letdown.

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    Focus On Sport/Getty Images

    Baltimore Orioles fans can be forgiven for weeping this season as the O’s limped to a 47-115 finish and traded key assets such as infielder Manny Machado and reliever Zach Britton.

    In 1969, however, Baltimore endured an arguably more painful fate.

    The Birds soared to a 109-53 finish behind Hall of Famers Brooks Robinson and Frank Robinson but lost in five games to the New York Mets in the World Series.

    This series is remembered for the “Miracle Mets,” who’d been a laughingstock prior to ’69, but the O’s deserve their portion of blame for falling short.

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    Transcendental Graphics/Getty Images

    In 1930, the Athletics defeated the Cardinals in the World Series, 4-2. In 1929, they won it all in five games over the Cubs.

    In 1931, Philadelphia won 107 games behind legendary manager Connie Mack and again faced the Cards in the Fall Classic. Continued dominance seemed inevitable.

    Al Simmons had hit .390. Lefty Grove had gone 31-4 with a 2.06 ERA. The stage was set for a three-peat.

    Instead, the Cardinals flipped the script and won the series in seven games.

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    JEFF HAYNES/Getty Images

    Subtracting the 1994 strike-annulled season, the Braves made the playoffs ever year from 1991 to 2005.

    They won the World Series only once during that span, in 1995 against the Cleveland Indians.

    We mentioned the 104-win 1993 season. But the Braves’ biggest “what if” was 1998, when they won 106 games and the National League East by 18 games behind the trio of Greg Maddux, Tom Glavine and John Smoltz.

    Rather than rolling to another title, Atlanta lost to the San Diego Padres in six games in the National League Championship Series.

    If we’re dinging this dynasty, getting dumped by the Friars was not a good look.

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    Uncredited/Associated Press

    What’s the most memorable moment of the 1954 World Series?

    If you answered anything other than “The Catch,” aka Willie Mays’ indelible over-the-shoulder grab, you’re incorrect.

    Then again, the Indians won 111 games that year. The Giants won 97.

    Yet the Giants swept the series. Mays got his catch. The Orange and Black won three more even-year crowns long after a cross-country move to San Francisco.

    The Tribe fell flat, on the other hand, and haven’t snagged a championship since 1948, the longest active drought in the game.

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    JEFF ROBERSON/Associated Press

    In 1906, the Cubs finished 116-36, the best regular-season winning percentage of all time. This was the team of Tinker to Evers to Chance, a myth even in their time.

    The Cubbies cruised to the best record ever and seemed destined for greatness.

    To the contrary, they lost in six games to the crosstown rival Chicago White Sox, who had finished last in the AL with a .230 batting average.

    The Cubs would win the World Series in 1907 and 1908 before the Curse of the Billy Goat kicked in, but this was among their darkest chapters.

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    JOHN FROSCHAUER/Associated Press

    The Seattle Mariners have never won a title. They “boast” the game’s longest active playoff-free streak of 17 seasons.

    Let’s hop in a time machine and go back to 2001, when the M’s were the toast of both leagues.

    Seattle finished that season with 116 wins, mere winning-percentage points behind the ’06 Cubs. That said, Seattle’s choke was and is more painful, both because of their ongoing futility and the early nature of their playoff exit.

    A 27-year-old Ichiro Suzuki hit .350 with 56 steals. Second baseman Bret Boone hit .331 with 37 home runs. The M’s had future Hall of Famers on the rise and dudes in the midst of ludicrous career years. This was their moment.

    Or not.

    Seattle’s playoff foray ended ignobly with a 4-1 series loss to the Yankees in the ALCS. The M’s didn’t even taste the World Series, let alone sip champagne.

    The Yanks, in turn, lost to the upstart Arizona Diamondbacks in a seven-game World Series, but if the Mariners took any comfort in that outcome, it was the coldest kind.

       

    All statistics courtesy of Baseball-Reference.

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