Sell, Sell, Sell! The 9 Most Embarrassing Owners in Professional Sports

Owning a sports team requires a lot of things:a commitment to winning and a big ego. Unfortunately, these two things tend to foul each other up. The best owners in pro sports are the men behind the curtain who surround themselves with talented management and leave it to the team to take the glory rather than themselves. The best owners are willing to wave goodbye to easy money for the sake of the team and the city. The following 9 owners are not like that at all.

9. Dan Gilbert
Dan-Gilbert-150Dan Gilbert was doing a fine job with his team, managing one of the few points of pride for Clevelanders. Of course, that job was made a lot easier by LeBron James, whose acquisition by the Cavs turned out to be the best thing to happen to Cleveland since…well, ever.

With all his eggs in that one basket, it’s easy to understand his anger and frustration when LeBron took his talents to South Beach and threw up two middle fingers to his former fan base with the debacle that was “The Decision.”However, what’s not understandable was the vitriol that spewed forth from Gilbert following James’ departure. Using a public forum, he went apeshit on James, calling him every name in the phone book while accusing him of checking out during last spring’s playoffs.

While the behavior of Gilbert was childish and petty, it was also short-sighted. When players see an owner like that, it doesn’t exactly cause them to want to start lining up at the Q to throw on a Cavs Jersey.

Oh, and Dan – promising to win rings in Cleveland before LeBron does with arguably the strongest basketball squad ever assembled? You may have overextended yourself there, chief.

8. Jerry Jones
Jones_Jerry_150Owner/GM. Is there a more terrifying combination of roles in the world? The combination of these titles allows unchecked spending (and ego) to reign supreme. While Jerry had tremendous results in the mid-90’s, since then it’s been a bumpy ride. His ego has caused numerous fallouts with his coaching staff, resulting in a steady stream of mediocrity following Switzer’s departure.

I mentioned ego before, and I’ll mention it again. The Egyptian’s have nothing on Mr. Jones when it comes to building shrines to themselves. The new Cowboys Stadium is a testament to unchecked ego and hubris. The fact that it’s really, really cool doesn’t mitigate that. People were willing to overlook Jones’ faults when the Boys were winning rings, but it’s been a while, so he’s back under the microscope, and many wish he’d spend a little less time on the field mingling and a little more time restoring the dynasty.

7. Mark Cuban
spart-d22cuban2-150x150There are certain things to love about Mark Cuban. During his reign, he has turned the Mavs around from perennial laughing stock to one of the NBA’s elite teams and a constant playoff presence. He’s created one of the best arena experiences in the NBA with American Airlines Center. And no one seems to be more personally invested in his team’s success than Cubes.

It’s that last one that gets a little tricky. Cuban is so close to his players and staff that when it comes time to make an unpleasant decision, no one’s sure if he can pull the trigger. The last time he had to wave goodbye to a player and friend, it was Steve Nash, who ended up getting two consecutive MVP’s with the Suns.

Pair his buddy-buddy relationship with the players with reality TV show appearances on both Dancing with the Stars and The Benefactor, and while you may have an owner that’s good for the team and the league at the end of the day, he’s not without a cringe factor.

6. Madison Square Garden Inc./James Dolan
james-dolan.lFor all intents and purposes, Chairman and CEO of MSG Inc James Dolan “runs the show” in NYC. I used quotes when saying “runs the show” cause that’s actually not what he does at all. 3rd grade lemonade stands have been run better than the iconic franchise. Despite cavalier spending over the past 15 years, the Knicks have yet to turn out one player that matches the caliber of a Patrick Ewing (or maybe even a John Starks). Instead, Dolan tosses the keys of the franchise to walking punch-line Isiah Thomas, who should have taken a cue from George Costanza and followed the opposite of what his instincts told him on every managerial decision.

While hope springs in MSG, the track record suggests that it will take a lot more than wild spending on overpaid free agents, crappy draft picks, and unwavering fan loyalty to turn this thing around. Which may never happen if the MSG board can’t find someone with more capable hands than Mr. Dolan.

5. Peter Angelos
Angelos EditedThe headlines in Baltimore are ubiquitous: “The Birds Have Flown South This Fall.” When your team is perennially described with such hackneyed phrases about underachieving, the best place to look for change is at the top. SI dubbed him one of the five worst owners in the MLB, and said that he took the least scientific approach to team leadership of any owner in the league today. Hardly high praise.

They kicked off the season 2-16, and while they were able to turn the ship around once Buck Showalter stepped in late in the season, I wouldn’t start the presses on those “Baltimore Orioles Division Champs” shirts just yet.

4. William Clay Ford
small_fordsr_mugFire Matt Millen! Fire Matt Millen! Guess what the one thing the Detroit Lions owner refused to do for years and years and years? Bingo.

Millen was single-handedly destroying this team through both inaction and ridiculous draft picks and acquisitions, and the one person who could stop it, Ford, sat on his hands as one of the NFL’s most historic franchises turned into the football’s answer to the Clippers.

As an NFL owner, your biggest job is this – keep the stadium full so that the fans can watch their team on TV. Well, as recently as 2008, the Lions had to black out 5 of their last 6 games, with the exception being the gimme Lions home game on Thanksgiving. With the popularity of the NFL, especially in a Midwestern city like Detroit, the inability to perform that simple task means it’s time to hand over the keys to someone who can. It’s a shame city hall can’t step in (then again, look at Detroit’s City Hall). Things are looking better for the Lions these days, but certainly not good.

3. David Glass
David Glass 150Upon his arrival as interim CEO of the Royals in ’93, Glass cut the payroll by more than 50%. Then he urged owners to refuse to negotiate with the players in the days leading up to the strike. Then he advocated the use of scrub players when the players did strike.

He’s become a successful owner in the sense that he makes a lot of money for himself by cutting costs at every opportunity for a personal gain, but of course, that’s not exactly what a city looks for in an owner. Lots of guys can get rich owning a sports team, but only a few can win while they do it. If that’s the guy you’re looking for, you best look past Mr. Glass.

2. Donald Sterling
donald-sterling-150x150How excited can you be about a guy that takes a symbol of your town (a sports team) and runs it just like an insurance brokerage firm, with no regard for the sanctity of the sport or the city?

Well, Mr. Sterling, since buying the Clips 30 years ago, has done just that. He has made no bones about making sure everyone knows his concern is the bottom line and nothing else. Win, lose? Doesn’t matter to Sterling, who has figured out that people love sports so much that they’ll pony up to see a bad team, so why spend money on making a team good.

In more recent years, he’s loosened the purse string a little, but it hasn’t made much of a difference. Baron Davis was a poor fit for their offense and hasn’t been the spark that everyone hoped he would be.

Oh yeah. Allegations of sexual harassment and discriminatory hiring practices have been floating around almost as long as Sterling has been there. You run a tight ship, Donald.

1. Al Davis
Picture-9-150x150Where, oh where do we start with the crypt keeper? There was a time when he was a model owner. His teams won, he had incredibly progressive hiring practices, having hired the first Hispanic coach, the second black coach, and a female team president. But that was…a long time ago.

Despite some successes in the early 2000’s which you may or may not admit included a blowout loss in the Super Bowl to Tampa Bay, Davis’ reign since moving the team back to Oakland has been a comedy of errors. Their draft picks have been monumental disasters, their coach’s office has had a revolving door of characters, all of dubious moral fiber (look no further than Tom Cable to see what I’m talking about).

But the good news is that Al Davis will never die and has promised to keep the team until they win two more Super Bowls, which should happen sometime around 2712.

Tags: Al Davis, David Glass, Donald Sterling, James Dolan, Jerry Jones, Mark Cuban, Peter Angelos, William Clay Ford,