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:

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20 Michael Jordan – NBA – Owner, Charlotte Hornets

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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.

As we saw with the coaching career of Wayne Gretzky, widely regarded as the greatest hockey player ever, greatness in your sport doesn’t always translate to success behind the bench or in the press box. Well, maybe he's not so bad. He did bring the Hornets name back.

19 Jason Licht – NFL – GM, Tampa Bay Buccaneers

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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.

Fast-forward 13 weeks into the season and the experiment is not going as planned for the Bucs. They sit at 2-10, although miraculously still alive in a historically bad NFC South, with their lowlight being a 56-14 dismantling to their rival Falcons. Mike Evans has proved to be a great draft pick however and will surely be great for years to come. However, their free agent pickups have not played well and seeing Revis having a great season in New England is surely not thrilling for Bucs fans. It turns out, the team on the field can't even count to 11!

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

via chatsports.com

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.

E-mails surfaced later proving that the plan to move the Sonics out of Seattle was in the works prior to purchasing the franchise. Can you say con artists?

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.

He was justifiably fired this past offseason. It's paid immediate dividends for the Canucks, who find themselves near the top of the standings.

16 Paul Holmgren – NHL – GM, Philadelphia Flyers

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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.

This hurts Flyers fans even more looking at the Kings success after the trade. Los Angeles has made the playoffs every year, reached the Western Conference Final (2013) and won two Stanley Cups (2012, 2014). The Flyers on the other hand, have not gotten past the second round of the playoffs during that time.

15 Jim Crane – MLB – Owner, Houston Astros

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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.

It’s nice and all to be saving money, but in 2013, when your highest paid player is playing on a one-year, $1.15 million contract, don’t ask why your team is finishing dead last in the standings. This past season, Crane increased payroll and won 19 more games than in 2013 but the team still ranked last in the league in payroll.

14 Peter Angelos – MLB – Owner, Baltimore Orioles

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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.

Nine managers have been hired during his tenure and even though Buck Showalter has changed the losing culture in the past couple of years with two playoff appearances in three years, Angelos is still Angelos.

13 Reggie McKenzie – NFL – GM, Oakland Raiders

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Although the late Al Davis gets the brunt of the blame for the Raiders’ struggles this past decade, Reggie McKenzie has not exactly done much to help the team. At the very top of questionable moves, firing Hue Jackson after his first season as head coach after leading the Raiders to an 8-8 record (only their second non-losing season since 2002) and replacing him with Dennis Allen. There are still major doubts concerning that move and following the firing of Allen earlier this season, it’s safe to say it did not exactly pay off. There is no stability in Oakland and the Raiders will be stuck at the bottom of the standings until that is fixed.

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

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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.

Phillies fans can only hope that the free fall has hit a plateau and that team is headed back to the top.However with Amaro Jr. at the helm, there’s not much reason for a sunny day in Philadelphia.

11 Charles Wang – NHL – Owner, New York Islanders

via newyork.cbslocal.com

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.

Wang was a rich man who acted prematurely in buying the team as he’s publicly stated that he regrets ever purchasing the franchise. At least he shares the same sentiment as the fan base. Thankfully for Islanders fans, Wang is on his way out as owner and the team has suddenly seemed to turn the corner.

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

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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.

In terms of value though, MLSE is doing well. The Maple Leafs remain the most valuable team in the NHL despite the lack of success on the ice and the Raptors value is now on the rise as well since the company named rapper Drake as its ambassador. Forbes now ranks the team as the 18th most valuable in the NBA.

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.

Although always having one of the highest-paid rosters in the league, it did not pay dividends as the Knicks are more often than not near the bottom of the standings. Though Thomas is now gone, his impact is still felt. The Eddy Curry trade only exemplifies everything that is wrong with the Knicks franchise.

8 Gary Bettman – NHL – Commissioner

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Every time he speaks, you realize that there is such a thing as a human bobblehead. But that is the least of Bettman’s worries. Under his watch, the NHL has endured THREE separate lockouts. The fact that he is still the commissioner today is a miracle in itself.

7 Jeff Loria – MLB – Owner, Miami Marlins

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Master of deceit, Jeffrey Loria took over the Montreal Expos only to later sell the team to the MLB after the city of Montreal refused to build him a new stadium. After abandoning the Expos and leaving Montreal without its team, Loria bought the Marlins. He then somehow managed to convince the city of Miami to build him a new billion-dollar stadium and then proceeded to trade all of his talent. Now, Loria is one of the 47 people who are in attendance at Marlins games. Mission accomplished Loria!

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

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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.

Even so, as other owners are quick to dismiss their head coaches, Brown is the complete opposite. The prime example of this is current head coach Marvin Lewis. This is his 12th season as head coach now, second longest tenure behind only Bill Belichick (who’s been to the Super Bowl five times and won three of them during that time). Lewis on the other hand, has five winning seasons and no playoff victories to show for it. After so many years of mediocrity, it seems as though Brown is content with just making it to the playoffs.

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

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Although he is no longer the owner of the Clippers, Donald Sterling still deserves a spot on this list. Prior to the emergence of Blake Griffin in 2011, Sterling had owned the team for 32 seasons and his team had made it to the playoffs four times. In April 2014, Sterling was banned from the NBA for life and fined $2.5 million by the league after private recordings of him telling then girlfriend V. Stiviano “not to bring (black people) to my games”.

4 Roger Goodell – NFL – Commissioner

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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.

This season has only added more stains to Goodell’s resume. The way he has dealt with two separate off the field incidents has been controversial to say the least. Claiming he had not seen the Ray Rice footage prior to its public release, he decided to suspend Rice for two games but then extended the suspension for no apparent reason other than the backlash there was concerning the light original suspension. Just when you thought it couldn’t get any worse for Goodell and the NFL, the Adrian Peterson situation arose. Goodell's seat is getting warmer.

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

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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.

His new stadium, often referred to as “Jerry World”, boasts the world’s largest 1080p HDTV hanging above the field and its capacity reaches 105,000 including standing room. For all of the flashiness Jones brings, the Cowboys have been mediocre for quite some time. After winning three Super Bowls in the early 90’s, the Cowboys have won exactly one playoff game since their Super Bowl XXX victory. Jones the owner is fine, but Jones the general manager is a big reason why the Cowboys have had such a lack of success for close to 20 years.

2 Daniel Snyder – NFL – Owner, Washington Redskins

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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”).

Making Albert Haynesworth a $100 million man turned out to be the worst signing in recent memory and perhaps of all time. But the lack of stability at the head coaching position has been especially troubling. With this year’s hiring of former Cincinnati Bengals offensive coordinator Jay Gruden, the Redskins are on to their eighth head coach in Snyder’s 14 years as owner. Yikes. Oh and there's this certain controversy surrounding his team's name that he continues to deflect.

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

via theguardian.co.uk

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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