5 Most Heartbreaking Moments In Chicago Sports History

5 Most Heartbreaking Moments In Chicago Sports History

In the wake of the latest Chicago sports fail, I look back at some of the city's most harrowing history. The build up to epic letdowns, the surefire wins that become stunning losses, and of course the favorite's that come up short to expectations. The tragedy's that rock the entire city.

As I See It looks at the Top 5 Most Heartbreaking Moments in Chicago Sports history.



5.) Olympic Sized Failure


The bid was up for the 2016 Olympic Games. Chicago, was seen by many as a favorite to win, competing with Tokyo, Madrid, Rio de Janero and Spain, Chicago attempted to sway the International Olympic Committee in Copenhagen to austerity. With a Presidential backing from the hometown First Couple Barack and Michele Obama, Chicago appeared poised, laden and well-equipped to bring the games to the city of broad shoulders.

However, it was not in the cards for Chicago. Destiny would put the city's opportunity to host the games on hold. Chicago was one of the first to be eliminated, an utter shock that surprised the entire city and many across the country. There was plenty of blame to around as well. Many believe that the spike in crime and corrupt government were to blame as well as a weak proposal and congestion in the city. Whatever the case, this was an epic heartbreak in Chicago's history, both in sports and culture.

The anticipation

The letdown



4.) The One That Got Away (Blackhawks Game 7 loss to Montreal Canadians)

Tony "F*$@#&%" Esposito

1970-71 was the dawn of the new playoff format in the NHL. Teams were in opposite divisions were allowed to criss-cross in competition for the first time. This would also be the Chicago Blackhawks first season in the Western Conference, a move that would prove both beneficial and heartbreaking.

The Blackhawks made light work of the Philadelphia Flyers, a 4-0 sweep to move on and play the New York Rangers. The series went 7 games with the Hawks winning game 7. They would then face the 3rd seeded Montreal Canadiens.

In a back and forth series, the Blackhawks shut out the Canadiens 2-0 in Game 5 to back Montreal into a must win at home. Game 6 went the way of Montreal, beating Chicago 4-3 to force a game 7 to be played at Chicago. This game would be known as the Tony "F*$@#&%" Esposito Game.

Esposito came into Game 7 ranked second in goals against only to Montreal's Ken Dryden - who despite anemic throughout the playoffs, held his own to lead the Canadiens to the Stanley Cup Finals. However, it was the Blackhawks who took a 2-0 lead late into the second period. That's when Esposito became small, as Jacques Lemaire scored on what many called a seemingly easy save for Esposito, followed by Henri Richard's consecutive goals to finish the Hawks at home and walk away with the Stanley Cup trophy.

Utter heartbreak in Chicago.



3.) Chicago Black Sox Scandal

In perhaps one of the blackest clouds ever to be cast across the city and league, the Chicago White Sox were involved, implicated and eventually found guilty of trying to "sell-off' the 1919 World Series to the Cincinnati Reds. A claim that found the Sox intentionally losing games in efforts to give the championship to the Reds. Eight members of the White Sox team were banned for life those players were,

  • Pitcher Eddie Cicotte
  • Center Fielder Oscar Felsch
  • First Baseman Arnold Gandil
  • Outfielder "Shoeless" Joe Jackson
  • Utility Infielder Fred McMullin
  • Shortstop Charles Risberg
  • Third Baseman George Weaver
  • Pitcher Claude Williams

Also St. Louis pitcher Gedeon was banned after investigations proved he placed bets upon discovering the fix from Risberg. In efforts to gain a reward, Gedeon attempted to blow the whistle on the plot, but instead was banished from baseball by federal judge Kenesaw Mountain Landis.

The fix went like this, Chuck Gandil with the assistance of Arnold Rothstein sports gambler  - who had alleged ties to the criminal element - hatches the plan to throw the series who then tells Cicotte of his plans. Cicotte agrees to join for an estimated $10,000 which was to be paid before the series. Gandil then recruits other Sox players to join and recruits the assistance of a sports gambler for an estimated $80,000 then seals the fix for $100,000 with a third party gambler Sleepy Burns.  The players agreed to throw the first 3 games and win the fourth.

Rothstein then placed $270,000 on the Cincinnati Reds to win the World Series, as well as Gandil and Risberg. As suspicion of a fix rises due to unclosed mouths, the odds were eventually set to even, with the Reds winning Game 1 of the World Series 9-1.

The fix was in.

In a series of ill-advised cut off throws, unconscionable errors and visible guilt plagued 1919 World Series. For money players - who at that time, were either poor or lower class - despite the fame of profession were forced to jeopardize their own integrity for financial gain.  A decision which will forever live in baseball infamy.

And in Chicago especially.


2.) Derrick Rose Tears ACL

The freshest of wounds, Chicago Bulls reigning MVP and future Derrick Rose suffered the most severe of sports injuries - a torn ACL - as Chicago went to close out Game 1 of the 1st Round of the NBA Playoffs against the Philadelphia 76'ers. In one swift move to the hoop, the Bulls chances of avenging the Eastern Conference loss to the Miami Heat, and any hope of making a run at the NBA Finals were eviscerated.

Rose blossomed into a star utterly from Day 1. With under a 2% chance of landing the No.1 overall pick in the 2008 draft the Bulls landed the lottery pick at number one and selected the Chicago native out of the University of Memphis. As serendipity would have it, the young guard instantly became Chicago's franchised players since former Bull and 6-time NBA Champion Michael Jordan. Rose earned Rookie of the Year followed by an All-Star start and ultimately the NBA's Most Valuable Player Award last season.

Then it was gone in one swift move to the hoop.

The more disturbing of the injury is the type. There are a laundry list of athletes who have suffered the degree of tear similar to Rose's and have never been the same( Sixers' head coach Doug Collins, Lakers GM Mitch Kupchak, and perhaps the most debated of all, New York Knicks All-Star and leading scorer Bernard King -which whom it took nearly 2 years of rehabilitation to garner half of his ability. However, there are some players (Jamal Crawford, Kendrick Perkens, Ron Harper, Mark Price, and most recently David West, who suffered his ACL tear just a year ago and is playing as close to his old self as any player who has come back from such an injury) who come back as good or arguably better than before.

Derrick has a long path ahead of him, as we all pray for his full recovery, we mourn as a city proud, appreciative, and heartbroken.


1.) Death of the Legend (Walter Payton Dies Nov. 1, 1999)

Chicago has enjoyed some great triumphs in the world of sports throughout history. None of which more poignant as the 1985-86 Chicago Bears Super Bowl run. And at the front of that run was the greatest running back in NFL history, Walter Payton.

Payton, or "Sweetness" as he was called by fans and teammates alike because of his personality and athletic grace, was the enigmatic style of speed and power the league had ever seen. From his hard-work ethic, to the way he carried the Bears offense up and down the field to pay-dirt, Walter epitomized what it is to be a Chicagoan. His character out-shined his Hall of Fame career, in a blend rare to sports or life.

Walter beat many opponents, offensive lines, intimidating linebackers and safeties throughout his 13 season career. He also rewrote the records books in the process, holding the career rushing yards record after retirement and netting over 21,800 yards total.

Unfortunately the one battle he lost, ultimately cost him his life. While working to beat sclerosing cholangitis, a rare liver disease, a bile duct form of cancer was discovered. This would eventually claim the life of the legend and on November 1st, 1999 the city and world lost one of it's true heroes.

Payton left behind his wife (Connie), a son (Jarrett) and daughter (Brittney) as well as a legacy bigger than the state of Illinois.


Leave a comment
  • DePaul's losing to Larry Bird's Indiana State in the 1979 NCAA tournament ranks up there too.

  • In reply to Aquinas wired:

    That would have absolutely made the list. There were quite a few honorable mentions. Bartman being a close call to the 70-71 Blackhawks

  • Great idea for a list. I'll only going by things I've experienced...

    5. Cubs' 2008 loss to Dodgers in NLDS
    4. Blackhawks blow 4-1 lead to Penguins in Game 1 of 1992 Cup finals.
    3. DePaul's first-round loss to St. Joe's in the 1981 NCAA tourney.
    2. Cubs' 2003 loss to Florida in NLCS
    1. Cubs' 1984 loss to San Diego in NLCS

  • In reply to Jimmy Greenfield:

    Good list, I was there for the 2008 NLDS. Pretty sure Manny homered in every game at Wrigley. It was hard not including the Cubs in this list, just too many heart breakers to choose from.

  • It's heartbreaking that there can be so many:

    1. Hue Hollins' blown call on Scottie Pippen leads Knicks to series victory in 94, when Bulls were poised to win it all without Jordan.

    2. Bears win only one Superbowl with possibly most talented roster in NFL history.

    3. Wood and Prior break down.

    4. Hawks toil away for decades without home games televised

    5. Jordan retires for the first time.

  • I know.. 1 and 5 were on my short list for this post. I believe I had like 25 total. Very unearthing write to say the least, but it was fun.

  • For me it was the MLB strike back 1994. The whitesox had a good team that year. World series was doable that year.

  • I thought I would see the Cubs 2003 NLCS loss to the Marlins on this list. As a Cubs fan, really thought 03 was their year. No arguments on #1 and #2 as those was probably the most depressing days of my life as a Chicago fan.

  • Ya the 03 Cubs were a super close miss to the Hawks, it didn't make only because there were more games to be played. That Hawks Stanley Cup was a Game 7 loss. Couldn't have been more close to having it than that.

  • Brian Piccolo

  • In reply to donnadale:

    OMG. that should be number 2.. sob

  • trying to resist admitting that 2003 NLCS was one of the happiest sports days in Chicago history.



  • No way that Derrick blowing out his ACL can be on this list. Too recent. And they were not going to win it all even with him at 100%, much less the 50-75% they were going to get. Forget Miami -- OK City would have waxed them. Sad, but way too recent to put into perspective. As a Cub fan, of course I would have included the 1984 (Leon Durham) and 2003 meltdowns -- if you reject Bartman for being just Game 5, how about Kerry Wood hitting a home run in Game 7 and then losing? But since I do NOT hate on the Sox, I would also include the 1983 Britt Burns 10-inning heartbreaker with Tito Landrum homering. But I agree with Donna Dale on Brian Piccolo - that's number one. Walter was the greatest, but he had a full career and lived 19 years longer than Brian. And they were both funnier than hell. Brian, when asked if he would room with his best friend, Sayers (as the first integrated roomies on the Bears), told Ed McCaskey, "All right. I'll room with him. But he can't use the bathroom." Final note: Tony Esposito was awesome beyond compare. He had one lapse -- still the greatest goalie in Blackhawk history. We could use him now -- probably as he is, at this point.

  • In reply to KetchupHotDog:

    Absolutely on this list. Between him and Walter Payton, no two athletes have meant more for their city than them. When it happened doesn't affect how the city felt afterward. I don't think anyone expected or could have anticipated that injury and it's impact on a favored season.

  • In reply to Curtis Shaw Flagg:

    No two athletes other than Payton and Derrick have meant more to this city? Now you're just talking nonsense. What are you, twelve? Derrick isn't even top of the list of BULLS who meant something to this city. He might not even be in the top two. But I do want you to remember yesterday's date. It's the date where you said Derrick Rose meant more to Chicago than Michael Jordan did. :D

  • In reply to KetchupHotDog:

    Derrick Rose means more to the CITY of Chicago than Michael Jordan absolutely. Jordan wasn't from here, Jordan never contributed to the direct community OUTSIDE of wins.

    Walter Payton wasn't from the Chicago but effected the city more outside the lines than any other athlete. Not only is Derrick Rose the face of the city, but he is a native which whom kids in the inner city can relate to and residents can applaud and be proud of. I have no problem standing behind that comment bc Michael brought championships to Chicago, Derrick has brought hope.

    We ALL love Jordan in Chicago, but make no mistake, this is DERRICK's city. When he went down, there was nothing more impacting and talked about throughout the city in my years of existence. Not to mention the complete break down of the team due to that fact.

    I would encourage you to name someone outside of MJ on the Bulls who means more to the city than Derrick Rose, since you brought it up!

  • In reply to Curtis Shaw Flagg:

    Uh, how about Scottie Pippen, voted one of the 50 greatest players in NBA history, and the second-best Bull ever after Jordan? Derrick was an all-star a couple of times and an MVP once; Pippen was also an MVP once (in one of the only two prime seasons he got to play outside of Jordan's shadow) and is an inner-ring solid NBA Hall of Famer. If Michael had never existed, Scottie would have owned this town just as much as Derrick has. Just comparing career with career, Pippen was a defensive monster and an offensive ignitor whose points were only limited by having to play second fiddle to Jordan. Sadly, Derrick may already be done, at least the Derrick we knew. Players have come back from this injury, but none I know of has ever come back as anything close to the player they were before. Watch. If Derrick comes back as the Derrick of old, I will eat my words. But if he does not, mark my words, he's not going to be the man around here anymore. People love incredible moves, like Jordan had and Derrick had; when those moves go away, as they did even for Jordan, well, he had better win, or he'll turn into Cliff Pondexter or Reggie Theus in the public mind. That's why I said it's too soon for anyone to measure the impact of this injury or to say it's up there with Walter dying or the Black Sox. We're still talking about the Black Sox 93 years later. NO ONE will be talking about Derrick's injury in 30 years, much less 90. And here's my proof: it's only been 27 years since Michael Jordan missed almost a whole season to a bad foot injury...and neither you nor anyone else even remembers that. And that was MICHAEL JORDAN. Who, no matter what you say, not only owned this town lock stock and barrel, but owned the entire earth. He single-handedly made basketball a world sport. I lived in Greece for a couple of years while he was playing, and I was treated like a king because I was from Chicago and played playground and semi-pro ball over there (at a low, low level!). Yao Ming would have been a soccer goalie without Jordan. And in this town, Jordan was God Almighty, the answer to the question, "Will we ever have a stone-killer winner on one of our teams?" ...Your youth is showing, my friend -- but enjoy it! Thanks for the exchange.

  • In reply to KetchupHotDog:

    And on the age thing. You don't know how old I am which makes the comment a bit moot. However, I've watched EVERY game Michael Jordan has played in it's absolute entirety. Still doesn't change me living in the city of CHICAGO and understanding the impact both he and Rose has.

  • In reply to KetchupHotDog:

    Your bias for Jordan is showing. And I will dismiss the Scottie Pippen comment. Scottie Pippen is not Derrick Rose in this city. They won championships, that ALL they get. It appears your thinking more narrow in the aspect of an IMPACT in the city.

  • In reply to Curtis Shaw Flagg:

    "Bias for Jordan?" Hee hee... That's like being a Yankee fan and saying I have a bias for Babe Ruth, or being an Edmonton Oiler fan and trying to say Gretzky just can't match the impact of Ryan Nugent-Hopkins because Wayne was from Ontario and not Western Canada. And your third sentence has the right tense: "Scottie Pippen IS not Derrick Rose in this city." You are so present-focused that you can't see Derrick in perspective. This Bulls team has yet to draw a million people downtown the way the Jordan teams did 6 times. THAT is the way to the heart of a city - WINNING. And do you really want to throw down on Chicago, IL cred? Friend, I can read your bio. You grew up downstate. I grew up in Chicago, Illinois. I lived through the whole Jordan time and I've lived through the Derrick time (in fact I lived through the Jerry Sloan-Norm Van Lier-Bobby Love-Chet Walker time), and the response to a winning team here is magnitudes bigger than anything we have seen with Derrick. Who is a nice guy and a local, I'll grant you. But he's never going to draw that million people downtown until he wins...and the odds are, the career aftermath of this injury is going to look a lot more like Kerry Wood or Mark Prior than Tommy John. Much less Michael Jordan.

    Nice try, Decatur! ;)

  • In reply to KetchupHotDog:

    I agree about Piccolo, but Payton's meant alot more to the city. I hate to compare those types of things. I also think that Esposito's instance was a rare lapse, but that made it all the more worse.

  • '71 Black hawks definitely, I would also go with 2003 Cubs or '69 Cubs, how about the '75 Bulls when Detroit and Dave Bing just squeezed past a great Dick Motta team? Someone mentioned the '79 Depaul team, though I always thought the loss they suffered in 1981 to St. Joes was more heartbreaking, because they shouldve made the final four that year. The Olympic thing? Thats not really a sports moment.

  • In reply to mikechi59:

    Thanks for reading! The 03' Cubs pretty much barely missed the short list. As far as the Olympics, tell Chicago native Olympic gold medal speed skater Shaunie Davis it wasn't a sports loss. I really enjoyed making the big board for this list and may do another one with my honorable mention, although some of the mentions could have easily made the list.

  • (How could I have left off the '69 Cubs, THE seminal heart-crushing event of my youth?)

  • We could do a Cubs heartbreak for about every year after 1908

  • In reply to Curtis Shaw Flagg:

    Your heart can't break after the 40th time or so...too much scar tissue!

    No hard feelings! Keep up the good work. You have to have known that a list like this was going to get a strong reaction from us old farts!

  • In reply to KetchupHotDog:

    Decatur was the place I was born. Just so you know. Like I said before you are looking at championships, that is it. I am talking about personal impacts on the city. Not just for a day of celebration. I understand that some of this is new. However it doesn't discount it's significance. I think that is where we differ. Doesn't matter if it happend 40 years ago or yesterday, it's impact was heavy and still hasn't settled.

    I do thank you for reading and engaging, I don't write for everyone to agree!

Leave a comment