Even though the Boston Red Sox won the World Series in 2004 and 2007 I feel I should add them to this poll. That was one heck of a cursed team for 86 years. But this will cover all 4 major sports in North America. Which team is the most cursed? I got the idea when I wanted to see just how bad Leafs fans have it in comparison to other sports. Toronto Maple Leafs - No Cup since 1967 and the longest Cup drought in the NHL. Never reached the Cup final since then either. Have the obstacle of Gretzky's high stick in their way along with losing to weak opponents in the Hurricanes in 2002. Not to mention the curse that Ballard seems to still have control over Chicago Cubs - No World Series since 1908. No World Series appearance since 1945 when the "Billy goat" curse was brought upon them. Had the Babe Ruth called shot go against them in the 1932 World Series. Lost in 1945 in 7 games. Have the Leon Durham error in 1984 which was the first time they had been in the postseason since 1945. And of course there is the Steve Bartman fiasco in 2003 that opened up an 8 run inning against. Wow. Boston Red Sox - Traded Ruth away in 1918. Never won until 2004 and had some awful years in between with unusually dramatic losses for one team. 1946, 1978, 1986 and 2003 are all years lost in Hollywood dramatic fashion. The name Bill Buckner, Bob Stanley and Bucky "Freakin" Dent come to mind as players that helped the curse continue. Buffalo Bills - Lost 4 straight Super Bowls in the early 1990s and now that we can look back, it was an actually great team they had. Scott Norwood helps the Bills curse move along nicely and the nickname Boy I Love Losing SuperBowls Not to mention the Music City Miracle against them in 2000. What luck, huh? Portland Trailblazers - Have to be the most cursed team in the NBA. Could have drafted Michael Jordan and passed on him. Should have beaten the Lakers in the 2000 semi final but choked in the 4th quarter.