Top 20 Horrible Bosses in Sports

Horrible Bosses saw Nick (Jason Bateman), Dale (Charlie Day) and Kurt (Jason Sudeikis) set out to kill their bosses. They plotted for days about how they’d murder each other’s bosses. What ensued instead was comedy at its finest, Jamie Foxx playing the best possible murder consultant, Colin Farrell as an absolute moron and getting murdered by a sociopath Kevin Spacey, oh and Jennifer Aniston as an absolute bombshell of a kinky nymphomaniac…in lingerie. Yeah, it was a great movie. The good news is that the three musketeers are back at it again in a much-anticipated sequel released this past weekend. With more and more people dealing with an unpleasant work environment, the first movie offered the all too relatable concept of a horrible boss. Let’s face it; everyone has had that boss who they simply cannot stand or that just isn’t good at what they do.

In sports, these bosses are critical to a franchise’s success. Someone who makes bad roster moves, coaching hires, or simply put, has set the team back with the choices they have made would qualify as a horrible boss. There are definitely different kinds of horrible bosses too. From the obnoxious overbearing ones to the silent killers, the one thing they have in common is that they are poison to the franchise or league.

So to celebrate Aniston looking as great as ever (watch the trailer) and to coincide with the release of Horrible Bosses 2, here is a list of the top 20 horrible bosses in sports today:

20 Michael Jordan – NBA – Owner, Charlotte Hornets

Sam Sharpe-USA TODAY Sports

Michael Jordan the basketball player is widely regarded as the best who’s ever played the game. Michael Jordan the owner has not been as successful. The team has struggled mightily during Jordan’s tenure, reaching a low point in the shortened 2011-12 season posting a 7-59 record, which was good enough (or bad enough) for the worst regular season winning percentage (.106) in NBA history.

19 Jason Licht – NFL – GM, Tampa Bay Buccaneers

Brian Spurlock-USA TODAY Sports

Yes, it’s his first year at the helm so how is it fair to put him on here? Well, Licht has carved himself up a spot on this list because of his public predictions of the Bucs going from “worst to first”. He brought in former Chicago Bears head coach Lovie Smith to run the team. In the offseason the team added 35-year-old quarterback Josh McCown to be their starter, safety Dashon Goldson, defensive end Michael Johnson and cornerback Alterraun Verner to replace departed Darrelle Revis. In the draft, the team added receiver Mike Evans and tight end Austin Seferian-Jenkins.

18 Clayton Bennett and Aubrey McClendon – NBA - Owners, Oklahoma City Thunder


Bennett and McClendon bought the Seattle SuperSonics in 2006 with every intention of moving the team elsewhere. However, this is not what they showed the city of Seattle and its fans as they claimed that they really wanted to keep the team in the Emerald City.

17 Mike Gillis – NHL – GM, Vancouver Canucks


After losing game 7 of the Stanley Cup Final to the Boston Bruins, the Vancouver Canucks have not won a playoff series since. The way he handled the goaltending situation has to be one of the most publicized failures an NHL general manager has gone through. Going back and forth with his goalies, he alienated Roberto Luongo only to then trade away Cory Schneider to New Jersey. Nine months later, Luongo was traded to Florida ending the long-running soap opera. To make matters worse, Gillis did not get much in return for either goalie.

16 Paul Holmgren – NHL – GM, Philadelphia Flyers

Eric Hartline-USA TODAY Sports

Paul Holmgren has flat out made bad decisions as Flyers’ GM. After reaching the Stanley Cup Final in 2010, the team has not been remotely close to getting back and Homlgren’s decision to trade Jeff Carter and Mike Richards to Los Angeles certainly hasn’t helped. At the time, it was a head-scratching move and has proved to be a terrible trade. The prospects Philadelphia received in the trade have not materialized and as much as Wayne Simmonds and Jakub Voracek are good players, they do not belong in the same conversation as Carter and Richards. With the cap space that was freed up with the trade, Holmgren went out to get goaltender Ilya Bryzgalov…enough said.

15 Jim Crane – MLB – Owner, Houston Astros

Brad Barr-USA TODAY Sports

This guy has the Mike Brown disease. He does not spend his money and therefore his output on the field reflects that. Acquiring valued players, signing star players and retaining your own talent are the main things you must do as a team owner when it comes to your players. You must also hire capable coaches and intelligent people in the front office to make smart moves. These are all vital to a team’s success. This is Owning a Sports Franchise 101, a class Crane clearly did not attend.

14 Peter Angelos – MLB – Owner, Baltimore Orioles


The Orioles made the playoffs only twice between 1993, the year Angelos purchased the team, and 2011. The lack of success turned off baseball fans in Maryland so much that average attendance dropped from over 45,000 in 1993 to just over 20,000 in 2011, an absolute drastic drop.

13 Reggie McKenzie – NFL – GM, Oakland Raiders

Kirby Lee-USA TODAY Sports

12 Ruben Amaro Jr. – MLB – GM, Philadelphia Phillies

Howard Smith-USA TODAY Sports

The Phillies had just won the 2008 World Series. They were on top of the world. Then, Ruben Amaro Jr. happened. Steadily declining ever since Amaro Jr. took over as GM, the Phillies lost the World Series in 2009, lost the NLCS in 2010, lost in the first round in 2011, missed the playoffs in 2012, fell under .500 in 2013, and posted an identical 73-89 record in 2014. That's a remarkably steady drop.

11 Charles Wang – NHL – Owner, New York Islanders


Here's all you need to hear; 15 years, $67.5 million. That is the contract that was handed to goalie Rick DiPietro back in 2006. At the time, big contracts were not a norm and this turned out to be one of the worst if not the worst signing of the decade as the oft-injured DiPietro rarely saw the ice.

10 Maple Leaf Sports & Entertainment - Owner, Toronto sports teams

John E. Sokolowski-USA TODAY Sports

Maple Leaf Sports & Entertainment, or MLSE, owns the NHL’s Maple Leafs, the NBA’s Raptors, the MLS’s Toronto FC and the AHL’s Marlies. The group, despite being worth more than $2 billion, has not had success with their teams. The Maple Leafs constantly underachieve and have not won a Stanley Cup since 1967. The Raptors have gotten past the first round of the playoffs only once despite being in the league for 18 years now. Toronto FC has never made the playoffs and win once every four games they play, adding up to a record of 62-120-74 since its inauguration in 2007.

To top it off, they price gouge their fans, despite the teams' lack of success. The Leafs are the most expensive team to watch (because fans love to pay ridiculous prices for a mediocre team).  In fact, Raptors playoff tickets last year were the highest in the NBA - more than the Spurs, who won the title and the Heat, who were defending champions at the time. The price jumped 242% from regular season ticket prices. You would think Mr. Burns was running MLSE.

9 James Dolan & Isaiah Thomas – NBA – Owner & GM, New York Knicks


Dolan and Thomas are on this list together as they both, as a team, managed to turn New York’s basketball franchise into the laughingstock of the NBA. Guilty of spending a lot of money and seeing no results on the court, they have made brutal decisions in the front office.

8 Gary Bettman – NHL – Commissioner

Bill Streicher-USA TODAY Sports

7 Jeff Loria – MLB – Owner, Miami Marlins

Steve Mitchell-USA TODAY Sports

6 Mike Brown – NFL – Owner/GM, Cincinnati Bengals

Aaron Doster-USA TODAY Sports

The Bengals were the joke of the NFL in the 90’s and early 2000’s, which earned them the nickname “Bungles”. Brown is the subtle and uptight version of Jerry Jones. He refuses to hire a general manager and even though the Bengals have now built a solid roster and have made the playoffs three years running, they have not won a playoff game since 1990. At one point, they missed the playoffs 14 consecutive years.

5 Donald Sterling – NBA – Owner, Los Angeles Clippers (1981-2014)

Kirby Lee-USA TODAY Sports

4 Roger Goodell – NFL – Commissioner

Kirby Lee-USA TODAY Sports

Roger Goodell’s time as NFL commissioner has been rough for the league, at least from the fans' perspective. With the NFL being referred to as the “No Fun League” nowadays, Goodell fines harmless behaviour but can't seem to get it right when dealing with a serious off the field issue. On the field, he’s taken away the added entertainment of creative touchdown celebrations. Somewhere up north, Chad Ocho…no wait he changed it back to Johnson-- is still feeling the aftermath.

3 Jerry Jones – NFL – Owner/GM, Dallas Cowboys

Joe Nicholson-USA TODAY Sports

Where to start? Jones is the outspoken, overbearing owner and GM of America’s team, the Dallas Cowboys. He and Cincinnati’s Mike Brown are the only two who hold the distinction of being both the owner and GM of their respective teams. Jones serves as the face of the franchise and sports fans have grown tired of his antics.

2 Daniel Snyder – NFL – Owner, Washington Redskins

Matthew Emmons-USA TODAY Sports

Between the team’s jarring lack of success throughout his time as owner, the terrible roster moves, the coaching carousel, his willingness to charge Redskins’ fans to come watch them practice and even ticketholders, Snyder sure has built his reputation as an awful owner. This is a rich man who attempted to play fantasy football in real life (we all know what happened with the Eagles’ “dream team”).

1 Vincent Tan – Football League Championship – Owner, Cardiff City F.C.


Tan sticks out as by far the worst owner in sports—and that’s saying a lot. He’s changed the traditional blue team color to red—mainly because he likes the colour red. The Malaysian billionaire did not help his cause by canning fan favourite manager Malky Mackay. But the most head-scratching thing of all has got to be that Tan requested to change transfer policy to only sign players with the number eight in their birthdate as the number is linked with good fortune in Malaysian communities. WHAT?

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Top 20 Horrible Bosses in Sports