The 25 Craziest Owners in Sports History

Team(s): Kansas City A's (now Oakland)
Years of ownership: 1960-1980
Craziest incident: Giving A's glass rings for second World Series because not enough players thanked him.

Charlie Finley certainly put his stamp on the Athletics' franchise, moving them from Kansas City to Oakland and overseeing three World Series titles in the 1970s. He was also the man behind a bunch of weird promos such as having a mechanical rabbit hand umpires new baseballs and trying to use orange baseballs during games. He also, at various points, employed the future Mrs. Fields and MC Hammer in various roles. Some of his players held a permanent grudge, though, when Finley gave them championship rings adorned only with green glass; he did it, apparently, because he only received three thank-you notes for  their first World Series rings, and was put off by the players' ingratitude.

Team(s): Wimbledon F.C., Cardiff City F.C.
Years of ownership: 1987-1997 (Wimbledon), 2000-Present (Cardiff City)
Craziest incident: Allegedly started burning players' clothes. 

Sam Hammam is current owner of the Cardiff City Football Club. Yet at one point, he was the majority owner of the Wimbledon Football Club. All Hammam wanted was his squad to be the hottest team on the field.

Literally.

Hammam has the reputation of being a practical joker. On his first day as a Wimbledon player, John Hartson walked into the locker room to find his Armani suit on fire. He told the Guardian:

I was thinking, "Jesus Christ, the dressing room is on fire!" But there was no fire alarm going off and everyone seemed to be laughing their heads off. As I got closer to the dressing room I saw that it was my suit that they were actually burning. I just couldn't believe it and, of course, it was all the clothes I had with me.

Now the incident was never traced directly back to the owner, but Hammam's reputation had preceded him. Anything like this would terrify a normal person. To Hartson, this was all a part of the "Wimbledon Way."

Team(s): Charlotte Bobcats
Years of ownership: 2009-Present
Craziest incident: Curating Possibly the Worst NBA Team Ever in 2011-2012.

We all know and can agree that Michael Jordan is the greatest basketball player of all-time. Six rings, six MVPs, etc. all prove that point. But when you start to talk about MJ's time as an owner, well...that's a tougher case to make. You immediately start hearing names like Kwame Brown, Adam Morrison, and numerous others. Jordan's ownership over the Bobcats has been rife with poor decisions, and he's now onto his fourth coach since acquiring the team in 2009. After bottoming out with the worst winning percentage in league history (.109) during the lockout-shortened 2011-12 season, things are looking up in Charlotte; the team is in the playoffs this year, and they'll soon become the Hornets again, replacing a mascot that the old owner reportedly named after himself.

Team(s): Chelsea Football Club
Years of ownership: 1982-2003
Craziest incident: Proposing that the Football Association implement electric fences.

Then-Chelsea Football Club owner, Ken Bates, was tired of the bullshit. The Chelsea football club was so rowdy, that in 1985 Bates proposed that the Football Association install electric fences to "deter hooligans." While we give him points for trying, we can understand why the Football Association promptly denied his request.

Team(s): Cincinnati Bengals
Years of ownership: 1991-Present
Craziest incident: Declaring Carson Palmer had retired after Palmer simply requested a trade.

The Cincinnati Bengals' owner has been known to ruffle a few feathers throughout his time in charge, despite the team spending most of that time completely sucking. The most downright childish of his exploits came from his handling of the Carson Palmer situation. In 2011, Palmer demanded that he be traded from Cincinnati. With four years left on Palmer's contract, Brown was obviously a little butt hurt. Instead of choosing to be a gentleman, Mike Brown instead told the media that Carson Palmer has retired and that the Bengals wish him well. Mike Brown, grow up.

Team(s): Fulham F.C.
Years of ownership: 1997-2013
Craziest incident: Installing a statue of Michael Jackson outside of Fulham's stadium.

Mohamed Al-Fayed does deserve some credit, as he is the one who helped guide Fulham from a lower level First Division side into a legitimate fixture in the Premier League. That isn't to say, though, that the Egyptian-born owner is not without his quirks. After Michael Jackson visited Craven Cottage for a game 12 years earlier, Al-Fayed had a statue of the famous singer installed right outside the stadium. When fans responded with equal parts confusion and consternation, Al-Fayed stated simply that "If some stupid fans don't understand and appreciate such a gift this guy gave to the world they can go to hell. I don't want them to be fans." Well OK then.

Team(s): Indianapolis Colts
Years of ownership: 1997-Present
Craziest incident: Criticizing Peyton for bringing in one ring. "We want more of these."

Colt's owner Jim Irsay's eccentricity resonates throughout the sports world. Whether it be from the mouth of his nearly unintelligible Twitter, or from the drug and alcohol exploits that landed him in rehab, Irsay's always got something for us. But my dude, Peyton Manning was the most beloved Colt of all time. He got you a Championship and gave his heart to the franchise. Crazy Jim, how you gunna do Mayor Manning like that with these comments?

"You make the playoffs 11 times, and you're out in the first round seven out of 11 times. You love to have the Star Wars numbers from Peyton and Marvin (Harrison) and Reggie (Wayne). Mostly, you love this." Irsay flicks up his right hand.

On that right hand? The ring that Peyton got him. There's ungrateful, and then there's Jim Irsay.

Team(s): Queens Park Rangers
Years of ownership: 2007-2010
Craziest incident: Asking for the names of fans who were booing him.

Starting out selling insurance and managing restaurants, Flavio Briatore worked his way and in 2007 took over Queens Park Rangers of England's Championship division (one rung below the Premier League). His time there was not a particularly happy one; he would regularly sit and "help" coach the team during games and fired numerous managers. All of these shenanigans and much, much more were shown in the film "A Comedy of Errors," a documentary released in 2012 that showed the world just how insane Briatore's brief tenure was.

Team(s): Boston Red Sox
Years of ownership: 1916-1923
Craziest incident: Selling Babe Ruth to the Yankees so he could put on No No Nanette.

The man who sold Babe Ruth from the Red Sox to the Yankees for $500,000, Mr. Frazee is inadvertently New York's greatest hero. And, really, the Ruth sale overshadows just how much he actually did for the Yankees. Strapped for cash pretty much throughout his time owning the Sox, Frazee sold player after player to New York for marginal returns, turning the team from a perennial winner into a laughingstock in just a couple of years.

Team(s): A.C. Milan
Years of ownership: 1986-Present
Craziest incident: Getting arrested for involvement in underage prostitution ring.

When Silvio Berlusconi bought AC Milan in 1986, he was just a wealthy entrepreneur with a healthy love of soccer. In the years since, he has acquired numerous other titles, some good (e.g., former Prime Minister of Italy, one of the richest men in the world) and some bad (convicted tax evader, frequenter of underage prostitutes). Yes, it's been a mixed bag under Berlusconi for the Rossoneri, but it has not been a run devoid of success; since he took over in 1986, Milan have won the Serie A league title eight times and the UEFA Champions League five times (easily the most of any European club over that stretch).

Team(s): Chicago White Sox
Years of ownership: 1900-1931
Craziest incident: Benching his star pitcher so he wouldn't make his bonus.

Charles Comiskey is notorious for being one of the most hated men in sports. The then-owner of the Chicago White Sox, Comiskey was a tyrant. The White Sox were known as having some of the filthiest uniforms in the league because Comiskey refused to fund laundry for the players, in order to cut costs. The dude benched his star pitcher, Eddie Cicotte, for the final five games of the season not because Cicotte was performing poorly, but because Comiskey refused to pay Eddie the bonus owed him by the White Sox. All this treachery planted the seeds of mistrust between the players and Comiskey that later led to the Black Sox Scandal in which eight players allegedly threw the 1919 World Series in order to get paid by the mob.

Team(s): Los Angeles Dodgers
Years of ownership: 2004-2012
Craziest incident: Hiring a psychic to send Dodgers good vibrations.

In 2010, the Los Angeles Times reported something ridiculous. Apparently, Los Angeles Dodgers owner Frank McCourt, summoned the ancient Rasputan-like magic of an old, former Russian scientist turned healer, named Vladimir Sphunt. McCourt paid this man for five years to send good vibes towards the Dodgers. Thank God, the "real" Magic came through in 2012. Thanks to Mr. Johnson and the front office, the Dodgers are heavy World Series Contenders this year. Vlad, take a seat man.

Team(s): Toronto Maple Leafs
Years of ownership: 1971-1988
Craziest incident: Using team money to pay for home renovations, motorcycles for his sons, and his daughter's wedding.

There's a special place in Canadian hell for a man named Harold Ballard. The former owner of the Toronto Maple Leafs had no regard for the team, its affairs, or the fans. He just cared about that green stuff, and what he could do with it. When the Beatles came to town, it was blazing inside Maple Leaf Gardens on the day of their concert. Instead of doing everything to cool the crowd down, Ballard ordered the thermostat to be jacked up. According to his New York Times obituary, he simultaneously delayed the show and told his concession stands only to sell large drinks, maximizing his profits. Later in his tenure, Ballard was accused of using the Maple Leaf's money to buy his sons motorcycles, renovate his home, and fund his daughter's wedding. All of this illegality eventually caught up with him. On the day of his court sentencing, the court room was packed. Ballard's one response: "We should have sold tickets."

Team(s): Cleveland Cavaliers
Years of ownership: 2005-Present
Craziest incident: Authoring the "Comic Sans letter" regarding The Decision.

In an open letter filled with elegant Comic Sans typography, Cleveland Cavaliers owner Dan Gilbert penned his reaction to LeBron's "Decision". Amidst other promises, Gilbert made the following statement:

I PERSONALLY GUARANTEE THAT THE CLEVELAND CAVALIERS WILL WIN AN NBA CHAMPIONSHIP BEFORE THE SELF-TITLED FORMER 'KING' WINS ONE

We're sure Cavs fans closed their laptops as slowly as we did. In 2010, a fired up Dan Gilbert wrote that letter with enough salt to season a steak. Since "The Decision," LeBron has garnered three MVP Trophies and two championship rings. Since "The Response," Dan Gilbert has racked up back-to-back-to back lottery seasons, and is eyeing a fourth. Sigh.

Team(s): Cleveland Indians, St. Louis Browns, and Chicago White Sox
Years of  ownership: 1946-1949 (Indians), 1951-1953 (Browns), 1959-1981 (White Sox)
Craziest incident: Signing little person Eddie Gaedel and sending him up to bat.

Ever the showman, Bill Veeck was all about the spectacle during his ownership tenure in baseball. As one of the last owners to enter the sport without independent wealth from other ventures, Veeck had to resort to other ways of bringing attention (and thus cash) to his teams. This included, but was not limited to: signing little person Eddie Gaedel, "Grandstand Manager's Day," and of course the infamous "Disco Demolition Night." While Veeck did many other, more important things for baseball such as integrating the American League and finally bringing Satchel Paige to Major League Baseball, his outside-the-box thinking and promotional ideas left an indelible mark on the history of the game.

Team(s): Dallas Cowboys
Years of ownership: 1989-Present
Craziest incident: Forcing Jimmy Johnson to resign.

We can say this about Jerry Jones: he absolutely, unequivocally loves the Dallas Cowboys and always will. He's one of those types, though, who will hold onto them so tightly that there's a good chance he ends up suffocating them. Upon purchasing the team, Jones made immediate waves by firing Hall of Fame coach Tom Landry (the only coach in franchise history) and installing himself as General Manager. His meddling has never really stopped, and while it initially worked well when Jimmy Johnson was at the helm, since then the Cowboys have failed to replicate that level of success; they've won exactly one playoff game since 1998, and have gone a mediocre 8-8 each of the last three seasons.

Team(s): Dallas Mavericks
Years of ownership: 2000-Present
Craziest incident: Working at a Dairy Queen for a day.

Mark Cuban has, most of the time, been a breath of fresh air for sports ownership. He genuinely cares about his team, supporting them like a fan would, and rips on referees just like the rest of us too. His bluster in the media made him a favorite target of former commissioner David Stern, who fined Cuban a total of 1.9 million over the course of Cuban’s 14-plus year ownership tenure. Perhaps his most memorable incident was when in 2002 he said that referee Ed T. Rush “wouldn’t be able to manage a Dairy Queen,” and then at DQ’s invitation Cuban himself went out and managed one for a day.

Team(s): New York Yankees
Years of ownership: 1973-2010
Craziest incident: Hiring a gambler to dig up dirt on Dave Winfield.

There's only one Boss, and George Steinbrenner set the gold standard for eccentric ownership. His acts of lunacy are almost too numerous to mention here, but we'll take a stab at it anyway. He went through 19 different managers between 1973 and 1990, hired/fired Billy Martin a total of five times, pleaded guilty to obstruction of justice and making illegal campaign contributions to Richard Nixon (which got him banned from baseball for 15 months), hired a goon to dig up dirt on Dave Winfield, who happened to be one of his own players (he earned a permanent ban from day-to-day management of the Yankees for that one), and throughout his time in charge was prone to ripping anyone and everyone publicly. It's safe to say he is a certified legend.

Team(s): New York Knicks
Years of ownership: 1999-Present
Craziest incident: Being named in the sexual harassment lawsuit against Isiah Thomas.

You'd be hard-pressed to find a group of fans who dislike their owner more than Knicks fans despise James Dolan. And honestly, we don't blame them. Dolan's judgment has proven to be awful time and again, and unfortunately there aren't really any reasons for optimism; after all, Dolan only ascended to this position because he inherited the company from his father. He kicked off his tenure by trading Patrick Ewing for Luc Longley in 2000, and really it has been one misstep after another since, from Isiah Thomas to Larry Brown to JD & The Straight Shot to (most recently) Ray Felton, J.R. Smith, and the entire 2013-14 season. After such a great run in the 1990s, it has been a rough go of it for Knicks fans.

Team(s): New York Islanders
Years of ownership: 1996-1997
Craziest incident: Buying the Islanders when he didn't actually have any money.

Detailed brilliantly in ESPN's 30 for 30: Big Shot, John Spano was a high roller who hung with the modern day American aristocracy. Spano cultivated a reputation so large and filled with charm, that he was able to lie his way into buying the New York Islanders...without any money. That's right, homeboy bought a whole NHL team with some sweet words and a smile. In an interview with WFAN's Joe Benigno and Evan Roberts, Spano said the following:

You just keep going down the road and people just assume that everything that's been told is accurate - and really people didn't check as much as maybe they should have. It was just as people have said - it kind of snow-balled; it was a perfect storm and everything. You know, when you have an owner that not only wants to sell but needs to sell, things are looked at a little differently.

Erm..if you can believe it, you can achieve it?

Team(s): Los Angeles/Oakland Raiders
Years of ownership: 1972-2011
Craziest incident: Filing an anti-trust suit against the NFL in 1982.

Before we start in on the more questionable moves of Al Davis' tenure, it's important to note how much good he did for the NFL, particularly on the civil rights front. He earned his spot in the Hall of Fame, no doubt. But still...damn. Davis was involved in almost too many lawsuits to count, suing the league on numerous occasions and basically becoming blood enemies with former commissioner Pete Rozelle. He continued to serve as the Raiders' General Manager until he died, and in his later years became so enamored of speed and flash that it led to disastrous draft picks like Darrius Heyward-Bey and equally bad free agent signings like Javon Walker. Davis also had zero patience for head coaches, going through five between 2004 and his death in 2011.

Team(s): Washington Redskins
Years of ownership: 1999-Present
Craziest incident: Refusing to consider changing the team's name.

It's pretty much the world vs. Dan Snyder at this stage, but we'll give the stubborn Redskins' owner this: he is refusing to give in. The people of Washington D.C. despise him, and the national pressure to consider changing his team's inherently racist name is mounting. You think Snyder cares? No chance. He said last May that the team will “never” change the name, and he hasn’t done anything to indicate otherwise in the almost one year since. For a list of his other misdeeds, this 2010 article from the Washington City paper is so exquisite, so scathing, that Snyder sued the paper for libel; the only problem was that it was also 100 percent accurate, and Snyder ultimately dropped the suit.

Team(s): Cleveland Cavaliers
Years of ownership: 1980-1983
Craziest incident: Trading every Cleveland first round pick in the mid-1980s.

You know you've done something really special when the league names a rule after you due to your own incompetence. In the case of Ted Stepien, he is the reason that NBA teams can no longer trade first-round draft picks in consecutive seasons. Why, you ask? Well, Stepien decided that the best way to turn his Cleveland Cavaliers into a contender was to mortgage the future by trading their first round pick literally every single year in the mid-1980s. Among the players they missed out on? Detlef Schrempf, Dennis Rodman, and James Worthy. It was so bad that when Stepien sold the team in 1983, the NBA gave the Cavaliers their first round picks back from 1983 through 1986 purely out of pity.

Team(s): Los Angeles Clippers
Years of ownership: 1981-Present
Craziest incident: Being sued by Elgin Baylor for racial discrimination practices in running Clippers.

The last couple years have been a remarkable reversal for Donald Sterling, who has spent the majority of his tenure as Clippers owner being subjected to scorn from all around the league. And while the success of Lob City has done much to paint over Sterling's ugly past, it's our job to bring it back to light. As recently as 2009, Sterling was in hot water with the Justice Department for refusing to rent apartments to African-Americans in Beverly Hills and to non-Koreans in the Koreatown neighborhood, as well as allegedly making numerous brutally racist comments to justify those practices. It's just the most recent in a long line of incidents that make Sterling one of the worst people to own a team, and that isn’t even touching the time he made fun of Baron Davis for being fat.

Team(s): Cincinnati Reds
Years of ownership: 1984-1999
Craziest incident: Calling Eric Davis and Dave Parker "million dollar n******."

You'd think someone who cared this much about her dogs would also care about the people who worked for her. In the case of Marge Schott, though, you would be dead wrong. Schott was one of the most notoriously racist, anti-semitic owners in the history of modern sports, a woman who had absolutely zero filter and treated pretty much everybody like shit. Among her more infamous quotes were saying that Hitler “was OK at the beginning” and calling Eric Davis and Dave Parker “million dollar niggers.” A lesser-but still gross-offense was her penchant for having her St. Bernards roam all over Riverfront Stadium and letting them go to the bathroom right on the field.