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The Grueling Truth - Where Legends Speak / The Grueling Truth's Top 10 Sports Lists / What’s Luck Got to Do with It? Top 10 Awful Cleveland Browns’ Decisions Since 1999 

What’s Luck Got to Do with It? Top 10 Awful Cleveland Browns’ Decisions Since 1999 

Publish Date: 03/14/2026
Fact checked by: Mark Lewis
Today we look at the top 10 awful Moments in Cleveland Browns history since 1999. There are a lot of bad moments for 26 years.

To be fair, hindsight is always 20/20. However, many of the Cleveland Browns’ horrific decisions came with warning signs plastered all over them.

For decades, a poor showing or bungled opportunities have plagued the team. Yes, sometimes bad things happen randomly for no apparent reason. These are usually attributed to bad luck. The following countdown shows that more often than not, the Browns are their own worst enemy.

Top 10 Worst Moments since 1999

10. General Manager John Dorsey– Whether you consider him a visionary with a nose for talent or a reckless nonconformist who took wild chances, John Dorsey seemed to help and harm the team in nearly equal measure. Bringing the likes of Baker Mayfield, Nick Chubb, and Jarvis Landry on board while also orchestrating the acquisition of Odell Beckham Jr. and hiring Freddie Kitchens to be the team’s Head Coach. Dorsey’s tenure as General Manager still causes occasional ripples in Lake Erie.

Video: 2017 Cleveland Browns Lowlights 0-16

2017 Cleveland Browns Lowlights 0-16

9. Julio Jones Goes to Atlanta—Let’s journey back to Draft Day 2011. At that time, the Browns held the 6th overall pick, and it appeared that the football gods were handing them an extremely talented Alabama standout, Julio Jones. Years later, Jones is known as one of the most dominant wide receivers to play the game and a future Hall of Famer. However, the Browns’ think tank traded their pick to the Atlanta Falcons, where Jones would make an excellent name for himself. Rather than a legendary talent, the Browns ended up with a bucketful of draft picks (27th, 59th, 124th in 2011, plus 2012 1st- and 4th-rounders), which they used poorly.

Video: Cleveland Browns 2011 Draft

Cleveland Browns 2011 Draft

8. The 2016 Draft Class– In 2016, the Browns drafted 14 players. Ten years later, none of these players is remembered for excelling in their position. To add insult to this gaping wound, the Browns also passed up chances to get quality players by trading down for more picks. Poor scouting? Probable lapses in judgment? Pure stupidity? You choose.

Video: 2016 NFL Draft Rd 1 Pk 15 | Cleveland Browns Select WR Corey Coleman

2016 NFL Draft Rd 1 Pk 15 | Cleveland Browns Select WR Corey Coleman

7. Hue Jackson– Because of his smarts as an offensive coordinator in Oakland and Cincinnati, as well as a respectable 8-8 record as the Raiders’ head coach, it seemed as if Hue Jackson would be a good hire in Cleveland. However, in his first season (2016), the team managed a single win, and in 2017, it was winless. There are numerous criticisms of Jackson, including poor game/clock management, underutilization of talented players, and a habit of blaming others for his shortcomings.

Video: The Most Miserable Coaching Tenure In NFL History

The Most Miserable Coaching Tenure In NFL History

6. The Trio from Harvard– Say what you will about analytics being the key to NFL success. On Draft Day, a room full of professionals with high football IQs is more helpful than a room filled with staff holding Harvard diplomas. In 2016, Jimmy Haslam brought Harvard alumni Paul DePodesta as Chief Strategy Officer, Sashi Brown as director of football operations, and Andrew Berry as head of player personnel. The hope was that NFL outsiders could help the Browns make meaningful changes. It begs the question: Will Haslam hire a plumber for his next colonoscopy?

Video: How Paul DePodesta Ruined the Browns

How Paul DePodesta Ruined the Browns

5. Odell Beckham Jr.- On paper, OBJ from NYC to CLE made sense. He was an elite talent, his best friend (Jarvis Landry) was a wide receiver on the team, and his energy seemed to match that of the other talented offensive players. However, things are not always what they seem. The reality was that Beckham was plagued by an injury from 2017, the Browns’ offense relied on the run, and Beckham brought unnecessary noise and drama to a team that was struggling. Add to that a lack of chemistry between Beckham and QB Baker Mayfield you have the recipe for failure.

Video: Odell Beckham Jr. arrives in Cleveland | Building The Browns

Odell Beckham Jr. arrives in Cleveland | Building The Browns

4. Almost Everything Surrounding Baker Mayfield– In and of himself Baker Mayfield was not a mistake. His behavior in Ohio Stadium was polarizing, and he was not the quarterback some Browns fans were hoping for in the 2018 draft. However, under the right circumstances, he could play well. Unfortunately, the Browns’ persistent chaos created some terrible circumstances.

During Mayfield’s four seasons in Cleveland, he had four different coaches: Hue Jackson, interim coach Greg Williams, Freddie Kitchens, and Kevin Stefanski. Not to mention various offensive coordinators.

Allowing Mayfield to play when obviously injured helped no one, especially Baker. Acquiring Deshaun Watson was the final chaotic move during Mayfield’s time in Cleveland. He was out the door soon after that trade.

Video: Baker Mayfield's Cleveland Browns Career Highlights

Baker Mayfield’s Cleveland Browns Career Highlights

3. Freddie Kitchens as the Head Coach– There was no doubt that Freddie Kitchens ran a solid offense, had a strong bond with Baker Mayfield, and was a catalyst for positive change under interim Greg Williams.  So, in their typical haphazard style, the Browns’ leadership made a pleasant man with no head-coaching experience, responsible for a role that requires strong leadership. For example, All- Pro Wide Receiver Odell Beckham Jr. joined the team in 2019, and Kitchens never had the fortitude to rein in the superstar. Everyone, players, fans, even parking attendants—knew Kitchens was in an impossible spot. Predictably, he was fired after one season.

Video: Cleveland Browns fire head coach Freddie Kitchens after one season | SportsCenter

Cleveland Browns fire head coach Freddie Kitchens after one season | SportsCenter

2. Johnny Manziel– Just hearing the former Browns QB’s name is enough to spawn facial tics. He highlights the many problems associated with an immature young athlete receiving massive fame and a hefty payday. His antics and lack of commitment to team policies led to Manziel’s release from the team.

Video: Hyped Up QB Debut is a DISASTER! (Bengals vs. Browns 2014, Week 15)

Hyped Up QB Debut is a DISASTER! (Bengals vs. Browns 2014, Week 15)

1. The Deshaun Watson Debacle– Everything about the Watson deal read like a cheap drugstore novel. The plot was so obviously bad, the screams of no, don’t do that were almost audible. Aside from awarding Watson a $230 million fully guaranteed contract, the Browns mortgaged their future. They gave up 2022 1st- and 4th-round picks, 2023 1st- and 3rd-round picks, and 2024 1st- and 4th-round picks. The sports world still considers this the worst trade in sports history.

Yet, in another example of 20/20 hindsight Browns’ owner Jimmy Haslam admitted, “We took a big swing-and-miss with Deshaun. We thought we had the quarterback; we didn’t”. Spend more time researching the potential effects of big deals, Mr. Haslam, and you won’t need to mix sports metaphors. Better yet, take a ride in the golf cart and let the professionals make the deals.

Video: The Worst QB Regression We've Ever Seen: Deshaun Watson

The Worst QB Regression We’ve Ever Seen: Deshaun Watson

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