The Minnesota Twins now hold a share of North American pro sports history, though it’s not exactly an achievement they’re proud of. With their loss to the New York Yankees on Monday night, the Twins were swept out of the first round of the MLB postseason, dropping three straight games in the best-of-five ALDS to bring their 2019 campaign to a bitter end.
This latest defeat at the hands of the Bronx Bombers is especially bitter, as it comes following a 101-win season for the Twins — the best regular season finish for the team since 1965. At this rate, Minnesota fans have to be wondering what they need to do to avoid a playoff matchup with the Yankees and win a damn game. Unfortunately, they’ll have another winter to think on it.
The only other MLB, NHL, NBA or NFL team to have such an unfortunate playoff run is the Chicago Blackhawks, who lost 16 straight Stanley Cup playoff games from 1975-1979. 
The Twins last won a playoff game in 2004, when they beat the Yankees in Game 1 of the ALDS. The Twins opened up the series with Cy Young winner Johan Santana on the hill and shut out New York, 2-0, at Yankee Stadium. Minnesota dropped the next three games to lose the series and begin their streak of playoff misfortune.  Minnesota last won a postseason series in 2002 when they beat the A’s in the ALDS before losing to the eventual World Series champion Angels in the ALCS. Since 2003, the Twins have qualified for the playoffs seven, with six matchups coming against the Yankees. In that span, New York has a combined record of 16-2. 
That third and final loss on Monday not only ended their season but it was also the Twins’ 16th straight playoff defeat —  a postseason losing streak that matches the longest in all four major North American sports leagues.  
Since that one victory, the Twins have been swept in the ALDS four times and come out on the wrong end of a Wild Card play-in game. The Yankees have essentially served as Minnesota’s boogeyman during that run, as all but one of those playoff matchups have come against the New York — meaning the Yankees are responsible for 13 of the Twins’ 16 straight postseason losses.