Which sports team has caused the most heartbreak for its loyal fans?

The Buffalo Bills, losers of four consecutive Super Bowls, have to be in the mix here.  The franchise has never won a Super Bowl - and, in classic Buffalo fashion, last won a title in 1965 in the old AFL... the year before the Super Bowl began.  Two words say it all: Wide Right.

Consider that for years (until DE Bruce Smith): the best player in Buffalo Bills history was... O.J. Simpson.  Ouch.

I could add that the loyal fans of this team pack an 80,000 seat OUTSIDE stadium every week, and freeze to death in God-awful weather conditions... to me, if you shiver and your team breaks your heart, it's worse than if you just suffer heartbreak.

I'm 41 years old.  The Bills have won zero titles in my lifetime; the Sabres (NHL) have won zero titles in 41 years; the Braves (NBA) won zero titles - then left town, to become the San Diego and now L.A. Clippers (and still haven't won a title).  So that's 123 years of futility, collectively; about 90 if you don't count the Paper Clips after 1976 departure from town.

It is amazing that Buffalo doesn't have more psychologists per capita than any city on the planet.  Sub-zero heartbreak... hurts.

Cleveland fans have a case.  The Browns have suffered excruciating heartbreak (vs Raiders on Sipe's INT and 4 missed FG; vs. the Broncos on The Drive and again on Byner's Fumble on the three yard line); the Browns haven't won since 1965... the Indians since 1948 (Mays catch in 1954; Mesa's ninth inning choke job in Game 7 of the of the World Series vs. the Marlins); and the Cavs... well, America felt for all of you after LeBron's "Decision."  It's hard when the star dumps you on national TV, agreed.

But hold on, Cleveland.  You got to see the greatest NFL player ever, Jim Brown, win multiple titles.  That's like having Michael Jordan play for your team.  We never had that in Buffalo.

That's my retort to Cubs fans, too.  Yes, it's been 103 years since the Cubs won... but every Cubs fan I know is a Bears fan (and got to enjoy Walter Payton and the 1985 Bears incredible D in that title season) and a Bulls fan (and thus got to see six titles with Michael Jordan).  If Michael Jordan played for a team you root for, you never get to complain about the heartbreak one of your other teams has caused.  Ever.  Because that would be like winning the $300 million powerball drawing, and moaning that you didn't win the state lottery drawing, too.  Got it?  So, sorry Cubs fans. You lose again here (hopefully, it wasn't heartbreaking). I call it the "Jordan Rules."

I'll accept the Cleveland Indians as an answer.  Grudgingly (see above), I'd actually accept the Chicago Cubs as an answer. But I believe Buffalo Bills fans have suffered the most.

And for cities - it's Buffalo or Cleveland, period.

John DeMarchi
Written Apr 17, 2011