Happy National Boss’s Day: Three Worst Bosses in Sports

Wednesday, October 16 is National Boss’s Day. Whether you love your boss or hate them doesn’t matter to us. We’re here to rank the three worst bosses in sports right now.

And it’s hard to believe that Bill Belichick is ineligible to make the list this year. There’s always next year.

3. Shad Khan, Owner, Jacksonville Jaguars

Khan bought the Jaguars in 2012. Since then, they’ve had the worst record in the NFL at 61-140. Even the New York Jets have won 71 games since 2012. Ironically, the Cleveland Browns have also won just 71 games since 2012, the same year Jimmy Haslam purchased the team.

Funny that the Browns, Jets and Jaguars all have bosses that seem inept. But Khan’s Jaguars have 10 fewer victories than the next two worst teams. That’s pretty bad.

After Gus Bradley went 14-28 as the head coach of the Jaguars, Khan replaced him with Doug Merrone, and things started to look up for the organization. In Merrone’s first season as the head coach, he brought the Jaguars to the AFC Championship. But Blake Bortles couldn’t defeat Tom Brady’s New England Patriots.

Over his next three seasons, Merrone finished in last place of the AFC South and did not return to the playoffs. In 2020, the Jaguars only won a single game, awarding them the No. 1 overall pick, which would become Clemson’s Trevor Lawrence.

Too bad Khan hired Urban Meyer to coach him. What a disaster, as the once-famed college coach was a comedy of errors that included inappropriate dancing in college bars and assaulting his kicker, Josh Lambo.

Perhaps Belichick will become eligible to crack this list in 2025 if Khan taps him as the new coach of the Jaguars. Surely that won’t backfire. 

2. Trent Dilfer, Head Coach, UAB

Dilfer is arguably a worse coach than he was quarterback. Ah, come on. That’s probably not being fair to the guy that threw 129 interceptions to 113 touchdowns throughout his NFL career.

After spending 13 years in the NFL, Dilfer dabbled in broadcasting before going on to coach high school football. In 2022, he was hired as the head coach of the University of Alabama at Birmingham (UAB). He’ll be the first to remind you, it’s not Alabama.

He seriously called his children up to the podium with him after a 41-18 blowout because “it’s not like this is freaking Alabama.”

Dilfer inherited a good UAB team and has sunk the ship in just two seasons. He’s 5-13 as their head coach, and he constantly seems to have more questions than solutions on how to turn the program around. 

It seems like it’s only a matter of time before UAB decides to go in a different direction.

1. John Fisher, Owner, Oakland Athletic’s

The first two bosses on this list were just flat out bad at their jobs. Not only does Fisher own one of the most irrelevant entities in professional sports, but he also made a gigantic ass out of himself in 2024.

Unless you live under a rock, you already know that the A’s are moving to Las Vegas. That’s about the biggest story surrounding the team in quite some time.

The A’s won the World Series in 1989. Since then, the furthest they’ve ever made it was the National League Championship Series in 2006, which was Fisher’s first season owning the team. Ever since? They haven’t made it out of the division series.

But let’s leave their failures alone. Fisher decided to move the team out of Oakland because the city was unable to reach an agreement with him on a new stadium. 

What’s better? He really didn’t have much of a backup plan. The A’s won’t play games in Las Vegas until the 2028 MLB season. In the meantime, Oakland will play their next three seasons at Sutter Health Park in Sacramento, home of the River Cats, the AAA affiliates of the San Francisco Giants.