20 Most Embarrassing Cleveland Sports Stories of All Time - Page 2

Cleveland sports fans are among the most loyal in the nation. Decades of heartbreak have hardened them, yet their passion never wavers. Still, even the most faithful can admit their teams have delivered some of the most embarrassing moments in sports history.

Think about John Elway’s infamous Drive in 1987, when the Browns were one stop from the Super Bowl. Or Jose Mesa’s meltdown in Game 7 of the 1997 World Series, when the Indians were one out away from a title.

More recently, who can forget the Browns giving Deshaun Watson the largest guaranteed contract in NFL history, despite endless controversy?

From “The Fumble” to Johnny Manziel’s spectacular bust, to the Cavs losing their hometown hero on live television during The Decision, Cleveland has seen it all. Painful as they are, these moments tell the story of a fanbase that keeps coming back, no matter what.

20. Paul Silas Firing (2005)

The Cavs were finally relevant with LeBron, then fired his coach midseason. The move created chaos and fueled speculation about the instability that haunted the early LeBron years.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

19. Andre Rison Signing (1995)

The Browns signed flashy WR Andre Rison, only for Art Modell to announce the team’s relocation weeks later. Rison became the symbol of Cleveland’s heartbreak during that nightmare season.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

18. Odell Beckham Jr. Trade (2019)

The hype was off the charts when OBJ came to Cleveland. Instead of fireworks, fans got frustration, drama, and a midseason breakup.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

17. Josh Gordon Suspensions (2013–2018)

Gordon was electric when he played — keyword “when.” Suspensions repeatedly derailed his career, leaving Browns fans to wonder what could have been.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

16. Baker Mayfield Fallout (2022)

He gave Cleveland its first playoff win since 1994, then was quickly cast aside. His ugly exit underscored just how chaotic the Browns’ front office had become.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

15. Bottlegate (2001)

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

14. Johnny Manziel Era (2014–2015)

“Johnny Football” was supposed to be the savior. Instead, he was a distraction, a bust, and a cautionary tale of hype gone horribly wrong.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

13. Tim Couch Draft (1999)

The expansion Browns took Couch with the first overall pick. He never lived up to expectations, symbolizing two decades of failed QB experiments.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

12. The Browns QB Jersey (2000s)

That infamous fan jersey listing all the Browns’ failed quarterbacks became a viral symbol of dysfunction. Each added name was another national punchline.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

11. 0–16 Season (2017)

Only the second NFL team in history to go winless. Fans held a mock parade to “celebrate” the futility.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

10. Red Right 88 (1981)

Instead of attempting a field goal to beat the Raiders, the Browns called a pass play. Brian Sipe threw an interception, ending Cleveland’s playoff hopes.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

9. The Shot (1989)

Michael Jordan buried the Cavs with his iconic jumper over Craig Ehlo. For Cleveland fans, it was another cruel chapter in the city’s sports misery.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

8. The Drive (1987)

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

7. The Fumble (1988)

Earnest Byner fumbled at the 2-yard line with the game on the line. Another AFC Championship, another nightmare ending.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

6. 2016 World Series Collapse

The Indians led the Cubs 3–1, then watched history flip against them. Instead of ending Cleveland’s curse, they ended Chicago’s.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

5. Deshaun Watson Contract (2022)

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

4. The 1995 World Series Loss

The most loaded Indians roster in decades lost to the Braves in six games. With all that talent, it felt like a massive letdown.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

3. The Decision (2010)

LeBron broke Cleveland’s heart on live TV, announcing his move to Miami. Fans burned jerseys, and the city became a punchline overnight.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

2. Jose Mesa’s Blown Save (1997)

The Indians were one out away from a World Series championship. Mesa couldn’t close it out, and the Marlins stunned Cleveland in extra innings.

20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com

1. The Move (1995)

Nothing tops Art Modell moving the Browns to Baltimore. The betrayal devastated a loyal fanbase and still stands as the single most embarrassing, painful moment in Cleveland sports history.

Cleveland sports fans have endured heartbreaks that would break most cities. From blown saves to botched signings and even losing a franchise, the lowlights are unforgettable. Yet through it all, Cleveland’s loyalty has never wavered. The very same fans who lived through The Drive, The Decision, and The Move also celebrated the Cavs’ 2016 championship and countless unforgettable moments. For better or worse, these embarrassments are part of what makes Cleveland sports so uniquely resilient.

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20 Most Embarrassing Cleveland Sports Stories of All Time  was originally published on newstalkcleveland.com