10. Bears Lose to Dolphins and Ruin Undefeated Season

In 1985, the Bears were the best team in the entire NFL.  To this day that ‘85 team is considered one of the best teams of all-time.  They routed the Patriots in the Super Bowl after going 15-1 in the regular season.  That one loss was the only blemish on their otherwise perfect campaign.  On a Monday Night in December the underdog Miami Dolphins, the only team to ever go undefeated with a 14-0 record in 1972, shellacked the Bears in a game to forget.

9. “Dollar” Bill Wirtz Runs The Blackhawks…Into The Ground

Wirtz managed the Hawks for 41 years.  His tenure was marked by stinginess with the fans and the players.  His antics ranged from blacking out games in Chicago to trading away Savard, Chelios, and Roenick.  No one wants to speak ill of the dead, but since his son Rocky took over things have improved significantly.

8. The 6-time Champion Bulls Break up

I know some will think this should be higher on the list, but it was expected and that team did give us 6 championships.  To be honest, we were probably lucky it lasted as long as it did, considering the animosity between most of the players, coaches, and the front office.  Regardless, it was a sad day to see the greatest sports dynasty of our generation finally break up.

7. Cubs Lose 3-1 Lead in 2003 NLCS

The 2003 Cubs were definitely not the best team in baseball record-wise, but they sure were hot going into October.  Then they ran into the eventual world champion Marlins.  While people like to point fingers at different people for why the Cubs blew their 3-1 series lead, everyone can agree that the results were tragic.

6. Michael Jordan Retires After His Father is Murdered

Michael Jordan’s retirement from basketball at the peak of his game in 1993 shocked the entire sports world.  The tragic events surrounding his father’s death stirred emotions inside all Americans.  Jordan went on to have a short, unsuccessful stint in baseball before returning to the game he loved and that loved him back.

5. Chicago Bulls Legends Stormin’ Norman Van Lier and Johnny Red Kerr Die Within 24 Hours

On February 26, 2009, the unthinkable happened.  The two longest-running and most respected members of the Chicago Bulls franchise passed away on the same day.  Johnny “Red” Kerr, former player, coach, and announcer for the Bulls had been sick for some time.  “Stormin’” Norman Van Lier, player and studio analyst, died unexpectedly.  Both will be greatly missed by all true Bulls and basketball fans everywhere.

4. Cubs Blow 9.5 Game Lead in Mid-August to Lose 1969 Pennant

The Cubs had a 9.5 game lead in mid-August over the Mets.  But those damn Miracle Mets just wouldn’t quit, and with the help of the Cubs losing more than 20 games in September, they went on to win the pennant and the World Series.  Supposedly the collapse all started with that black cat in a two-game sweep by the Mets up in Shea Stadium.  The Cubs were heavy favorites to win the NL that year and their collapse will go down in history as one of the worst ever.

3. “Sweetness” Walter Payton Loses Battle With Liver Disease

Walter Payton was the best running back who ever lived.  He was a hard worker on the field and one of the greatest people off of it.  A true role model for everyone, he died far too young after a battle with a rare liver disease called primary sclerosing cholangitis at the young age of 45 in 1999.  His memory will always live on in those who were lucky enough to see him.

2. 1919 Black Sox Scandal

There is a good argument that this should be number 1.  It is definitely the most embarrassing moment in Chicago sports history.  In a city trying desperately to shake its reputation for corruption to this day, the Black Sox scandal was just about the worst thing that could happen.  The 1919 White Sox were considered the best team in all of baseball.  Unfortunately owner Charles Comiskey refused to pay his players decent value for their excellence.  The players decided to make an extra buck by throwing the World Series.  Oops.

1. The Curse of the Billy Goat

Maybe its not the most embarrassing moment, or even anything if you don’t believe in curses, but this moment lives in infamy nationwide.  When Billy Sianis, owner of the Billy Goat Tavern, tried to bring his goat into the park during the 1945 World Series, he was refused.  He ended up cursing the Cubs.  Whether or not its the curse or just mismanagement of the team (or some combination of both), that stupid billy goat comes up every single year that the Cubs don’t win the Series, which is about 102 by my count.