Being only 25, alot of these heartbreaking moments did not happen while I was alive, or old enough to understand. I compiled my own list below of the worst moments in Cleveland sports history below since I became an active, emotionally invested fan.
Cleveland Indians - 1997 World Series and 2007 ALCS
That Cleveland Indians team in 1997 was my first love as a sports fan. Even now at 25, close to 16 years later. I still remember that night we lost game seven. The 2007 ALCS and losing the 3-1 series lead was awful, too. That team wasn't as loved and didnt have the expectations the '97 team did, but it was my first year in college, and every night of that postseason was a party. Knowing that if the Indians won the ALCS we would face the Rockies of all teams, and probably win the WS, that was just painful. The one thing that made me feel better was that with a young core I figured we would be right back there next year. Wrong.
Cleveland Cavaliers - The Decision, 2009 Eastern Conference Finals, 2010 Eastern Conference Semifinals
The Decision was obviously the worst off the court thing that happened to the Cavs, ever. The 2009 and 2010 postseasons were heartbreaking for what happened on the court. Considering the Cavs had the best record in the NBA both of those years, falling short of making the Finals was awful. In 2009 the Magic could do absolutely no wrong. In 2010... well, we know what happened. Couldn't even be mad about losing the 2007 Finals though because honestly we were just happy to be there.
Cleveland Browns - 2002 Wild Card loss to Pittsburgh, 2007 loss to the Bengals in week 15
That 2002 playoff game against Pittsburgh was so f'n Cleveland, man. Leading that Steelers team by 3 scores and having an offense that could not be stopped, only to go prevent defense and have Dennis Northcutt drop a game clinching sideline pass. I'm still not over the one. The 2007 loss to the Bengals was awful as you just knew that when we lost we weren't making the playoffs. We no longer controlled our own destiny and the Titans were facing a Colts team with nothing to gain by playing Peyton Manning the last week of the season. 2002 was worse as it was an actual playoff game, but that 2007 season was so exciting week in and week out, and to go 10-6 only to miss the playoffs stung. An honorable mention would be missing out on both Andrew Luck and RGIII in the draft. No disrespect to TRich, but if any team deserved one of those two QB prospects last year it was us.
Okay, well that was fun. I think I need a drink now.