17 Saddest Moments in Cleveland Sports History

Eddie PryceCorrespondent IAugust 29, 2011

17 Saddest Moments in Cleveland Sports History

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    I risk stating the obvious that it is rough being a Cleveland sports fan.  Torturous might be a better word to describe the experience, and over the course of time, excluding few breaks along the way in a sport or two, it has not gotten better.

    In the aftermath of the public embarrassment of the city of Cleveland and its fans during the “Decision”, and the juxtaposition of the 2010-11 Cleveland Cavalier team to both the 2010-11 Miami Heat AND the 2009-10 Cleveland Cavaliers simultaneously, many fans wondered to themselves (or out loud) “What is wrong with those Cleveland fans?”  “Why can’t they get over this guy?” “What a pity that city and its fans are…” 

    At face value, they have a point.  The simple decision of a grown young man that exercised his right to leave town through free agency left a town crying and on “suicide watch”, resulting in burned jerseys and the corporate cursing of their own native star.  Many young adults who have grown up in Northeast Ohio and migrated to other cities in the United States, why can’t LeBron?  After all, he blessed this city with it’s most exciting stretch of seasons in franchise history, took the team to it’s first Finals appearance and “gave it his all” while he played for the city of Cleveland.

    It is understandable to have that view, but I am immediately forced to wonder if the average fan really understands the history of Cleveland Sports and the unbearable number of painful setbacks and disappointments that this particular fan base has endured.  My guess is no. For if they did, they would not be so perplexed by the scorned behavior of Cleveland sports fan in the last year.

    Cleveland is not alone.  Many other franchises and cities have had their share of bad luck.  I live in a city (Chicago) where two baseball teams simultaneously experienced several decade-long World Series droughts dating back to early 20th century.  Philadelphia experienced an almost 30-year drought without a championship in any of their sports. Boston famously experienced futility dating back to Babe Ruth, and several franchises have either not seen glory in ages or never experienced it at all. 

    However, I challenge anyone to come up with a fan base that has had to endure more over the course of a long period of time with ALL of the teams in that city failing in freakish fashion, repeatedly. 

    Cleveland fans are as passionate as they come, and collectively NONE of the three major sports franchises have won since 1964.  Essentially, due to the Super Bowl starting 2 years after that championship, the Browns have NEVER won a Super Bowl (which defines modern glory). The Cavaliers have NEVER won a NBA Championship and the Indians have not won the World Series since 1948! 

    Combine the fashion in which Cleveland sports teams have managed to lose and I promise that after looking at this slide show you will never question the scorn and skepticism of a Cleveland sports fan ever again.

    These memories will live with Cleveland fans forever.

17. 2002 Playoffs vs. Steelers

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    Just three years into the Browns Part II the team got an opportunity to play their rival Steelers in a playoff game.  The Browns surprisingly got off to a great start and took control of the game early.  They looked poised to win a playoff game and possibly position themselves to make a run in the playoffs.  Instead, the Steelers made one of their biggest playoff comebacks in franchise history, coming back from a 24-7 lead in the third quarter to win 36-33. 

    This Steelers team was not quite as notable as the Steeler teams of the latter half of the decade, but the Steelers, still coached by Cowher at the time, had owned the rivalry since the Browns returned to Cleveland in 1999.  The painful thing about this victory is that this team brought back hope and a happy feeling in Cleveland of what it felt like to see a winning football team again.  That feeling was unfortunately interrupted by a game that drew comparisons to the John Elway led comebacks of the past. More on that later.


16. 2009 Eastern Conference Finals vs. Orlando Magic

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    The Cavs did not come into this year’s playoffs with quite the expectations that they had in 2010. However, after having had the top record in the Eastern Conference, there was great hope that the Cavs could get to the finals where they would meet the favorite L.A.  Lakers—whom they had success against during the regular season. 

    The much-anticipated match up of the league's two most premier players—Kobe vs. LeBron—seemed all but a formality when the Celtics lost Kevin Garnett to injury.  Instead, the Cavaliers were met by a buzzsaw when matched up against Dwight Howard and his Orlando Magic. 

    Night after night Dwight dominated the Cavs, while Hedo Turkoglu and Rashard Lewis caused match-up problems, creating easy baskets all series.  For the most part, LeBron had a very impressive series stat wise, and with the exception of a poor performance in Game 6, he held up to his end of the bargain.  But what became painfully clear was the lack of a supporting cast around him. 

    This seemed to open up the discussion of whether or not LeBron had enough around him to win in Cleveland, and how much this would effect his decision to leave the following year.  It can be argued that this was one of the first major wake up calls to LeBron that he may need to leave to obtain his championship goals.  This series alone sent the Cavs into panic mode trying to address their various needs in order to please LeBron. The Cavs would sign Shaquille O'Neal to be a low post presence to neutralize Dwight Howard and they would add more wing span and athleticism with Anthony Parker and Jamario Moon.  Looking back, this was the Cavaliers best opportunity to win it all, and they failed unexpectedly. 

15. Steve Olin Tim Crews Bob Ojeda Accident Spring ‘93

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    Some may not remember this tragedy, but this really shook the Cleveland community, as well as the rest of the nation. Three good players, still in their prime, that were expected to be a big part of the Tribe’s plans in ‘93 were involved in a tragic boat accident during spring training. 

    Beyond the sad tragedy of it all (if you take away the Tribe’s success to come later in the 90s), the team was coming off of years of futility and were finally expected to make a run at the division title. The Tribe had made several signings, including Tim Crews and Bob Ojeda, that seem to compliment their highly-touted young talented stars Albert Belle, Manny Ramirez, Carlos Baerga, Jim Thome, Sandy Alomar and Charles Nagy.  This crash effectively dashed away their hopes and, more importantly, left a hole in the hearts of many.



14. Jim Brown Retires

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    He was 29 years old and had just been named MVP of the league. Arguably the best RB of all time, Jim Brown decided to retire in the middle of his prime leaving the Browns without the heart and soul of their team and a Hall of Fame void in their lineup.  

    It is fitting that the Browns have not won a championship since Jim Brown retired prematurely.  If he had continued to play, it is very possible that the Browns could have been one of the first Super Bowl winners instead of the famous Lombardi led Packers. Instead, the Browns are still one of the few teams to have never won a super bowl.

13. 2007 ALCS Collapse

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    The upstart Tribe, after several false alarms during the 2000's in which experts made the sexy pick by saying the young Tribe were ready to finally contend, fulfilled the promise of their highly-touted talent.

    In retrospect, it is amazing to think that the Indians featured a pitching staff of elite studs like CC Sabathia and Cliff Lee at the top of their rotation followed by upstart Fausto Carmona, who was unhittable at times in 07.  

    The upstart Indians, up 3-1 on Red Sox in the league championship series, seemed poised to advance to the World Series.  They were playing dominant baseball for the majority of the season, especially down the stretch.  The Tribe seemed poise to return to the World Series ten years after their last disappointing visit in 1997. Then they were led by two future Cy Young Winners and several all-stars, only to get outscored 30-5 in the last 3 games to become victim to the generally unlikely 3-1 comeback. 

    Instead of showing you grainy video of Game 7 falling apart for the Indians, I’ll show you Jonathan Papelbon showing his elation about the improbable comeback and the JD Drew Grand Slam that broke Game 6 open.  You think the Sox and their fans weren’t excited?? 



12. The Afterparty

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    Well, assuming everyone knows that the Heat did not win the championship this year, it’s safe to say that this next moment was premature.  This “event” takes place just one day after LeBron gauged the hearts of Cleveland fans, in classless fashion. “Not 1, not 2, not 3…”

    Yeah, you get the point. 

    The Heat had quite a party and were greeted by a very hyped-up crowd, but if you had the fresh dislike for the Heat like most NBA fans did, especially those scorned in Cleveland, this moment hurt or even angered you as much as any other moment in Cleveland sports history.

11. The Shot #2—The Opportunity

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    In 1992, the Cavs had a very strong team (2nd best record in NBA) and this time had reached the East Finals for the first time since the 70s only to be dismissed again by their nemesis and regular player-hater Michael Jordan.  The following year, icing was put on the cake in yet another Cavs/Bulls series when Michael Jordan hit “The Shot II” over Gerald Wilkins.   Poor Craig Ehlo has got to have nightmares to this day about Mike.

    Also watch:


10. Red Right 88

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    The beloved “Cardiac Kids”, arguably the most likeable Cleveland Browns team ever to take the field on the lake front, time after time surpassed expectations during the 1980 season and won close game after close game in improbable fashion. Then in typical Cleveland fashion, against a team from California, the Browns had a chance on their last drive to defeat the mighty Oakland Raiders in a game that is well known nationally as one of the coldest games ever.  Wind chills reached –35 degrees during the game, and on the last play of the game, affectionately known as Red Right 88, wonder boy QB Brian Sipe threw an interception that just missed being the touchdown to send the Browns to their first Super Bowl ever.  Instead the Raiders went on to win the Super Bowl, and the Browns were left with a memorable season punctuated with a painful ending.

     It is said that Sipe made a bad read on the play and should have thrown it short to an open player on the 6, or thrown the ball away giving the Browns another crack, but hindsight is 20/20.  Again, Cleveland was so close with nothing to show for it.  Watch both for the rundown and context.



9. LeQuit

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    This was bad. The Cavs were the arguably the best team in the NBA. With the best record, they were favorites to win it all and were well positioned to take control of the series in a pivotal Game 5. Instead, during this huge game the 2 time-MVP, Lebron James, laid a complete egg.  The game, up to this point, is easily one of the worst performances of LeBron James’s seven year career and there was an eerie feeling about what was unfolding in front of Cavs fans.

    LeBron was the best player on the team and it was widely known that a big decision was ahead for him.  Anyone who has seen any significant amount of LeBron’s games knows that this just was not right.  Before all the conspiracy theories came out, (he later made it clear he did not think this team had a legitimate chance of winning against Boston after ultimately changing teams) this game left everyone baffled at his play.  How could this be?  Such a ferocious and limitless player, so talented, so competitive, and he seemed anything but interested in winning this game.  His dismissive answers at the end did not help the situation.

    This was as disappointing a moment for Cleveland sports fans as any in recent memory.  To many Cleveland fans, including myself, the writing appeared to be on the wall.  For the first time I became highly skeptical about whether he would be returning to Cleveland the following year. 

8. The Catch

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    This series is remembered, by most baseball fans, for the amazing catch made by all-time great Willie Mays. However, it was bigger than that. This 430-foot blast to center by Vic Wertz was a play that may have given the Indians the lead in the eighth inning, and hope in this series going home.  Cleveland will remember this as their best team ever getting swept in the World Series. 

    Again, only the Indians could pull this off, even in 1954.To add insult to injury, the Tribe did not make another world series for 41 years…

7. Benedict Arnold Part 1

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    Fast fwd to 1:20 on this video—if this does not do it for you, just keep in mind that Cleveland is, without question, one of the most passionate fan bases in the NFL. Cleveland has been known for years as a “Browns’ Town,” regardless of the recent love affairs with the Indians and Cavaliers over the course of the last 20+ years.  The football Hall of Fame is just a few dozen miles away, and the town whole area, including Canton, will always revolve around the Browns, win or lose. 

    To think that someone, for whatever reason, stripped this city of it’s football franchise for FOUR years is simply unfathomable.  Art Model, the same person that fired legendary coach Paul Brown, for suspect reasons, was the culprit here.  To add insult to injury (as is the theme here) Model won a NFL title with the Ravens in 2000. 

6. Dec 2, 2010

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    There may not have been a game more highly anticipated than LeBron James’s return to Cleveland after “The Decision”.  This was seen as a cathartic opportunity for Cleveland fans to show their “appreciation” for the treatment that he blessed the city with over the summer, and in the months leading up. This was a chance to show him, and the world, just exactly how the fans felt about his controversial performance in the playoffs against Boston, and the antics that led up to the nightmare ending of this fan/player relationship. 

    Unfortunately, although the fans were up to the moment, the Cleveland Cavaliers did not seem to grasp their role in this super sized drama that was unfolding around them.  Not only did the Cavs not come ready to play a competitive 48 minutes, but they proceeded to fraternize and show appreciation for their former teammate while the crowd was going ballistic and losing their minds in frustration towards their former golden-child.

    I feel this moment is as an all-time embarrassing moment in Cleveland history. After all LeBron put the city through, and all the hype and buildup to the game, the Cavs proceeded to let LeBron get the last laugh—and then some.  LeBron ended up being so comfortable and uninhibited on the court that he might as hell have worn a Cavs jersey again. The attention shifted from LeBron to the embarrassing behavior of the current Cavs.  From that point forward, the season tailspinned. The Cavs had several all-time lows and record-setting performances on their way to producing one of the worst year-to-year turnarounds in NBA history.

    LeBron got the last laugh.  Cleveland fans lose again.

5. The Shot

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    It was not cemented at the time, but looking back, the Cavs witnessed the making of a legacy that will remain unmatched by any other human being in NBA history.  Pre-LeBron, the Cavs teams of the late '80s and early '90s, led by Mark Price, Brad Daugherty and Larry Nance, were arguably the best in franchise history and had experienced great success. 

    In fact, in 1989 the Cavs were 57-25 and had the second best record in the East.  They swept the Bulls 6-0 during the regular season and finished 10 games ahead of them in the standings.  However, Michael Jordan and the Bulls were unphased by the circumstances. 

    After stealing Game 1 in Cleveland, the Bulls pushed the Cavs to a decisive Game 5.  The Cavs took the lead late 101-100 on a lay-up by Craig Ehlo, only to be beaten by one of the great game winning shots of all time.  As you watch this video, take a look at how many people he beat to get this shot off.  It is truly an impressive display  of uncommon will.

    The pain continues for Cleveland sports fans. This one felt different than the Browns travails, but it still hurt because there was a feeling of helplessness.

4. The Drive

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    AS a Cleveland fan, I suspect John Elway’s middle name is Lucifer.  Michael Jordan certainly was hated, mostly because he made a living of gnashing at our souls and hearts, but I cannot think of an athlete that was hated more by Cleveland fans in the '80s and '90s than John Elway.  There was just something about him.  Or maybe it was the fact that he led the Broncos to three AFC championship wins against the Browns! 

    “The Drive” fits in well with the other sports tragedies in Cleveland history. The Browns, 12-4 during the regular season and a favorite to represent the conference in the Super Bowl, had just scored with 5:32 remaining to take a 20-13 lead.  Keeping in mind context, this still remains one of the best Browns teams of all time. This was also, arguably, their best shot of making a Super Bowl to this day.

    The Broncos start their drive at the 2 yard line and Elway is able to methodically drive the Broncos, all the way down the field to tie the game up with less than 40 seconds remaining.  

    In the first of many occurrences, John Elway ripped victory from the mouths of the hungry Cleveland faithful.  The Broncos won in overtime with a field goal to win 23-20.  The video is worth watching in its entirety but the last minute or two show the end result.

3. The Decision

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    Ok, ok, you knew this one would come up.  I imagine you would put this highly publicized, heartbreaking moment at the top of the list.

    And I could have but I do not want to give LeBron that type of satisfaction. 

    Instead, since it was decided off of the court, “The Decision” that was made on July 8, 2010 is #3.   LeBron James, the 2-time MVP, and without question the greatest Cavalier to ever put on the uniform, decided to publicly “take his talents” to South Beach to join one of his contemporary rivals Dwyane Wade. 

    This one really hurt because it instantly dashed the hopes of a Cavaliers championship and cost the city one of it’s greatest revenue drivers.  More importantly, LeBron, the greatest source of pride that Cleveland sports fans had ever had ever laid claims on, was suddenly taken away. 

    No matter where a Clevelander lived, they knew about LeBron in his SVSM days and sat back proudly as the nation fawned over him as a teenager. Cavs games were nationally broadcast in the Lebron era because the Cavs were must see basketball. For the first time we had something that EVERYONE else wanted.  LeBron was ours.  He was born and raised in Northeast Ohio and played for our team with loyalty up until that point. 

    The Cavs organization gave him everything, the fans worshiped him, only to be left out in the cold (in public) and led through a charade for self-serving purposes.  Many say "get over it," but the way this situation went down was awful, in every imaginable way. 

    LeBron had a right to leave, but Cleveland fans have every right, based on all you have read thus far and the investment that was made in him, to feel as hurt and embarrassed as they were last June. 

    Also watch:


2.Edgar Renteria

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    Tribe fans waited forever for this moment. It has been 49 years since the Indians won their last World Series championship. The Tribe had managed to push the series to a decisive Game 7 in Miami, against the mighty Florida Marlins, led by an All-Star cast of stars near the end of their prime. 

    The Tribe entered the ninth inning with a lead, and Bob Costas was breaking down the historical context of what was going down like only he can.  Jose Mesa, who had an up and down career in Cleveland, was on top of his game and one of the league’s best closers at the time.  He took the mound with a 2-1 lead only to squander it on a single. A costly error by Tony Fernandez followed, setting up the game-tying sacrifice fly by lightweight Craig Counsell. 

    After a scoreless tenth inning, the Marlins grinded out their first World Series on a single by Edgar Renteria.

    This four year old franchise, which had been supported marginally (at best) over the years and ended up disbanding almost completely the year after winning, walked off with a championship. Meanwhile, the Indians passionate fan base was left again without a winner.  

    It just never makes sense how things tend to play out for the inhabitants of the “mistake on the lake”. 

1. The Fumble

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    This particular play represents the last time I remember the result of a game making me cry. 

    I am convinced I am not alone. 

    In 1987, the Browns played the rival Denver Broncos, led by vilified Hall of Fame quarterback John Elway. Coming off of a 10-5 strike shortened season and a AFC Central Division crown, the Browns were down 5 points, and on the verge of scoring the go ahead touchdown to send them to their first Super Bowl. RB Ernest Byner broke free, looking poised to score, and then he fumbled on the one-yard line.  One year after defeating the Browns in dramatic fashion in the championship game, the Broncos found a way to end the dream again. 

    To make things worse, Byner went on to win a Super Bowl just four years later in Washington.  Go figure!

    Also watch:


Honorable Mentions

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    Here are a few other bad moments in Cleveland sports:

    The firing of Paul Brown

    Every Major League movie

    2005 choke vs. White Sox

    The constant exodus of Cleveland Indians stars in 2000s

    OSU/Florida (football and basketball in same year)


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