heartbreak - Sports News, Headlines & Highlights

Deadspin Presents 'Heartbreak City,' to Make Fans Across North America Relive Their Worst Moments — Part 2: Two- & Three-Team TownsEvery year, 31 teams don’t win the Super Bowl, 30 teams don’t win the Stanley Cup, 29 teams don’t win the World Series, and 29 teams don’t win the NBA championship. There can only be one champion, after all....

The Official "It Gets Better" Letter Of The Tortured Sports FanTen years and two days ago, Aaron Boone's 11th inning home run capped another Red Sox collapse. The next morning, Tom Condardo typed out this letter and sent it to his two sons to officially welcome them into the heartbreak club....