The Dirtiest Dozen: The 12 Worst Owners in Sports

Jeff PencekCorrespondent IIAugust 1, 2009

There are plenty of candidates for a list of the worst owners in sports, and often bad luck or bad timing play a part in ruining a franchise. Sometimes the owner does put a lot of effort into the success of a team, ultimately failing because of the incompetence of a GM or a coach.

Then again, someone has to hire the GM or coach. I originally had the list started at 10 but a dozen stood out and had to be honored.


Honorable Mention

NBA – Clay Bennett (Definitely No. 1 in Seattle), Michael Heisley (the Memphis experience is awful), Robert Johnson (along with Michael Jordan showing mild interest in creating a winner) and the Maloofs (very personable yet have created a situation where Sacramento will probably move soon)

NHL – Jerry Moyes (would easily be a top 10 pick if he still owned the team), Maple Leaf Sports (Toronto is a mess of a team, amazing) and David Freeman (no offense to him, he just inherited a mess in Nashville).

NFL – Bill Bidwell (historically stingy and had a team make a fantastic Super Bowl run to keep him off the list), Jerry Jones (as an owner he’s great, his main problem is that he won’t look in the mirror and fire his GM),

MLB – Tom Hicks (Ran the Rangers as a mid market team for many years, spent so much on Liverpool he depleted his Rangers investment), Ted Lerner (he owns the Nationals, enough said), John Moores (the Padres have built themselves into a third-world team), Jeffrey Loria (he destroyed one team and gets to keep a second one mediocre).

12. Robert Sarver – Phoenix Suns – The luxury tax in the NBA is a dirty tool, making it very difficult for owners to keep talent together. However, the goal of the franchise should be to at least make NBA Finals, not to be under the luxury tax. Phoenix makes draft day trades solely for cap purposes, and yet they’re almost always still over the cap.

They actually traded a first-round pick and a player for a second-round pick. Sarver is obsessed with the tax, and then he makes short sighted moves that hurt the cap, like the Shawn Marion trade. 

11. Charles Wang – New York Islanders – Anytime the owner states that he regrets he bought the team, that’s not a good sign for a franchise. Signing middle of the road players to 10 year contracts like Alexei Yashin and 15-year contract for goalies is at least planning for the long term, although really strange planning since few goalies play 18 years in the league.

He also wants to move the Islanders if they don’t remodel the Nassau Coliseum and build a five-star hotel around it. I don’t know if anyone reading this has been around that area, but the only way there will be a 5 star hotel in that area is if Wang connects three hotels.

10. Ralph Wilson – Buffalo Bills – He’s headed to the Hall of Fame this year, good for him. Bills fans will pay him respect for everything he did for the community of Buffalo, up until this century.

Then something happened, where Ralph went senile I guess, and made every decision imaginable to harm the team and eventually pave the way for the team to leave Buffalo.

He won’t sell the team, and he won’t pass the team on to his family because of inheritance tax (yes the inheritance tax would stink, but they would also have a fantastic asset).

The longer he lives, the more likely it is that the team will move away from Buffalo and kill a community in the process. When the fans and the city need an owner to die, that’s the sign of a bad owner.

9. Peter Angelos – Baltimore Orioles – His situation may be more of a case of bad luck, where he is in a division with the crazy spenders in the Red Sox and Yankees. However, Baltimore has Camden Yards, and a very strong history, and zero success over the last decade.

My placement of Angelos on the list comes more from talking to friends and family in Baltimore, who have seen the absolute destruction of a once proud franchise. If Tampa can compete, Baltimore surely should be able to.

Angelos, like Wilson, has gained kudos from some for not selling the naming rights to the stadium even know it is additional revenue which would help their product. I don’t think Ravens fans were disgusted that the team plays in M&T Stadium considering they made the AFC title game last year.

8. Herb Kohl – Milwaukee Bucks – Milwaukee had a few good runs, but for the most part have been a strong lottery player for the last decade. The Bucks have recently been a part of some really bad decisions, including trading Mo Williams to Cleveland.

Being an owner should be a high priority, yet it’s a secondary job for Kohl, the democrat senator from Wisconsin.

Then again, maybe his senate job is his second job. Yikes. Kohl is a big believer in a balance budget, and also voted for the bailout. Most owners screw it up for their fan base. Herb’s screwing things up for all of us. Thanks Herb.

7. Larry Dolan – Cleveland Indians – Amazing how the Dolan name is synonymous with incredibly bad owner decisions. The recent achievement of Dolan was to trade Cliff Lee, which means he traded the Cy Young winner in back to back seasons.

That’s the way to build a winner. Dolan is from the mold of cutting payroll, and in 2007 the strategy looked like it worked since the Indians made the ALCS.

Now they’re back to laughing stocks, mostly because the Indians are always sellers. I’m not sure if a Wikipedia editor was an angry Indians fan, but I’ll post the next sentence as written.

“In June, 2009, Dolan suffered a mild heart-attack after picking up a roll of quarters that he intended to offer Cliff Lee as part of a new contract proposal.” Indian Fever, it’s catching fire with everyone.

6. William Clay Ford – Detroit Lions – It takes a lot of talent for an owner to create an 0-16 team, and very scary that five owners are worse. Ford’s biggest mistake is loyalty. Staying loyal to Matt Millen was one of the worst decisions in sports history.

The Lions are rarely competitive, and under Ford’s ownership, have made the NFC Championship game once. He doesn’t score so high because I believe he’s not as malicious as the others below him who actively seek failure.

5. Robert Nutting – Pittsburgh Pirates – He’s moving up the list with a bullet. Pittsburgh has titles in hockey and football, and the Pirates probably have the best ballpark in baseball. The Pirates also have a storied history filled with legends and great moments.

They should be able to compete. They should not resemble a yearly dispersal draft. Nutting works hard to create the worst team in baseball, and when the Pirates appear to be close or improving, more players get traded. Nutting has done some positives for the team creating the environmental initiative “Let’s go Bucs, Lets go Green”.

If he wants to go green, he should paint the seats at PNC park green, since he’ll see plenty of those every night with the minor league team the Pirates now have. Then again, that would cost money.

Breaking news, the Pirate Parrot and Captain Jolly Roger have been traded to the Buccaneers for Pegleg the Scurvy Riddled Pirate and three lower minor league mascots.

4. James Dolan – New York Knicks - I do have to give him credit, he is willing to spend money for talent, or his warped perception of talent. Anytime an owner runs a failure of a franchise and gets hit with a sexual harassment settlement that is a guy with motivation to stink.

New York should be the Mecca of basketball, yet have not been in the playoffs since 2001, and Dolan hired Isiah Thomas. Where Roger Federer and Tiger Woods compete in other sports, Thomas was in competition with Matt Millen.

The team has had zero chemistry, and have seemingly put all of their eggs into getting either Dwayne Wade or LeBron James in free agency next year. Good luck with that.


3. Mike Brown – Cincinnati Bengals – Anytime the season ticket holders initiate walk-outs and lawsuits against the owner, you can guess he ranks high on a list like this. During one time a few years back, I thought that Snake would shop up and Kurt Russell would have to Escape from the Cincinnati locker room.

He’s another owner who is relatively cheap with expenses (mostly his lack of a full scouting staff), yet refuses to sell the naming rights to the stadium which was supposed to make them more competitive.

He’s also the GM, and if a business genius like Jerry Jones struggles with that role, imagine how well Brown does it. You don’t have to imagine, the Bengals have won 35 percent of their games since he took over.

2. Al Davis – Oakland Raiders – Al Davis a few years back stated that he will not retire until he wins two more Super Bowls or dies of natural causes. Raiders fans have been put in the position of rooting for death.

Once again, Davis is another example that the owner/general manager model is an absolute failure when it comes to the modern NFL. Lane Kiffin was on a weekly firing watch and was screwing with Davis by wearing the wrong jerseys and attempting 76-yard field goals.

When the Raiders draft, it’s almost like every other team knows it will be a bad pick. Depending on his 40 time, Al would probably draft Captain Jolly Roger not realizing he was a recently traded baseball mascot. It might involve a strange marriage and swallowing some pride, but Al Davis should do what he can to rehire Jon Gruden.

He’s the only one who has had success under him, and it would probably speed up the natural causes.


1. Donald Sterling – LA Clippers – Before we get to the Clippers woes, let’s explore the extracurricular fun. During a trial, Sterling admitted to paying a Beverly Hills woman for sexual favors in buildings, offices and limos. Really if I had his money, I would do the same thing. Sterling met the woman at an Al Davis birthday party.

I wonder if Sterling, Davis, Brown and the Dolans hang out and throw crazy parties and hold Legion of Doom discussions on how they can destroy their teams. Blake Griffin should just fake a three-year injury and try to get to free agency in one piece.

Sterling has been spending a lot more recently on the Clippers, most of it horribly of course. He’s almost proving his theory of not spending to be correct, since he can lose just as much by being cheap. The Clippers failures are worthy of a book.

Let’s just say the Clippers have won one playoff series since Sterling bought the team, and they play in the second largest city in the United States.