Top 20 Craziest Owners in Professional Sports

Becoming the owner of a professional sports franchise comes with an almost immediate increase in reputation and stature. Regardless of how an owner acquired their massive wealth, once they purchase a team, their primary identifying quality is their status as a franchise owner. Along with this increase in statute comes increased scrutiny from the media and the general public. Under the watchful eyes of the public some of the eccentricities of these owners take the spotlight rather than the achievements of their respective teams.

Owners hold a unique position in sports. They wield more power than general managers, coaches, and players because they possess the ability to hire, fire, or trade almost any member of their organization. This power can sometimes become all-consuming and lead to their downfall, but often there are no real consequences for the outlandish actions of team owners. However, if an owner’s actions are patently offensive to the public or illegal, public opinion and fellow owners may turn against them.

Recently, owners are being increasingly forced to adhere to the rules and regulations that apply to players and other league personnel. Their outrageous actions are being dissected under the microscope of the media on a daily basis. Pundits make a living commenting on their lifestyles and the era of discretion among the media is over. In this new era, the personal lives of franchise owners is scrutinized with the same intensity that players receive. This new era has revealed that franchise owners can be downright crazy.

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20 Silvio Berlusconi – AC Milan

via theguardian.com

As the Prime Minister of Italy and the owner of AC Milan, Silvio Berlusconi is accustomed to being the subject of tabloid headlines. Despite being the owner of Italy’s three leading television channels, Berlusconi has been a frequent tax evader. He was sentenced to four years in prison for tax evasion, but had his sentence reduced to one year, which he spent on house arrest in a villa. He was also charged with soliciting an underage prostitute and hosting “bunga bunga” parties, which were essentially orgies with prostitutes. Berlusconi must pay his ex-wife Veronica Lario nearly $50 million each year as part of their divorce agreement.

19 Frank McCourt – Los Angeles Dodgers

via losangeles.cbslocal.com

In 2004, after a failed bid to acquire the Boston Red Sox, Frank McCourt successfully leveraged his ownership of a South Boston parking lot to acquire financing to purchase the Los Angeles Dodgers. McCourt eventually purchased the Dodgers from Rupert Murdoch for $430 million. He attempted to find success on the field by adopting Moneyball tactics and hiring Joe Torre, but both failed spectacularly. In 2009, Frank announced that he would be divorcing his wife of 30 years, Jamie. The divorce proceedings eventually caused the Dodgers to declare bankruptcy and the team was sold for a record $2 billion to a group led by Magic Johnson.

18 Dan Gilbert – Cleveland Cavaliers

David Richard-USA TODAY Sports

When LeBron James announced that he would be leaving the Cleveland Cavaliers for the Miami Heat, Dan Gilbert reacted in perhaps the most childish way possible. He wrote an open letter to his fans, using the font Comic Sans, that was a scathing criticism of how LeBron handled the situation. Four years later, Gilbert apologized for the letter and was able to secure LeBron James’ services via free agency. Time will tell if the move will bring Cleveland an NBA Championship.

17 James Dolan – New York Knicks, New York Rangers

William Perlman/THE STAR-LEDGER via USA TODAY Sports

As the President of both Cablevision and the Executive Director of the Madison Square Garden Company, James Dolan is accustomed to making business decisions. However, his tenure as the owner of the New York Knicks has been a downright disaster. It has seen scandal, such as the Isiah Thomas sexual harassment case, and many seasons of losing basketball for Knicks fans. Dolan spends his spare time singing in a blues band known as JD & the Straight Shot. He is also known for his temper and struggles with alcohol and substance abuse.

16 John Spano – New York Islanders

via whatnottodoc.com

John Spano nearly committed the greatest fraud in the hockey history when he purchased the New York Islanders from John Pickett. Spano misrepresented his wealth, claiming that he had inherited over $200 million from his grandfather. Spano was actually briefly the owner of the Islanders, thanks to forging documents from Lloyd’s of London to certify his wealth, but had difficulty making payments to various parties, including Pickett. These failures caused Spano’s scheme to fall apart, and he was eventually sentenced to serve 71 months in prison on charges such as bank and wire fraud.

15 Dan Snyder – Washington Professional Football Team

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Despite the Washington Professional Football Team using a racial slur as a team nickname, Dan Snyder remains fervently committed to upholding the term as an homage to Native American culture. Last Sunday, Snyder hosted the President of the Navajo Nation in his owner’s suite for Washington’s game against the Arizona Cardinals. He has recently been lampooned by South Park and denied a patent by the United States Patent and Trademark Office.

14 Donald Sterling – Los Angeles Clippers

Kirby Lee-USA TODAY Sports

Donald Sterling rocked the American social landscape when an audio tape emerged of him making racist comments to his girlfriend and employee V. Stiviano. He was eventually forced by Commissioner Adam Silver to sell the team to Steve Ballmer. Prior to this scandal, Sterling engaged in discriminatory housing practices and was fined $2.7 million by the Justice Department. Sterling has been the defendant in several sexual harassment cases. In 2010, Sterling even heckled his own players while sitting courtside with Baron Davis receiving the bulk of the abuse.

13 Marge Schott – Cincinnati Reds

via foxsports.com

From 1984 to 1999, Marge Schott served as the owner of the Cincinnati Reds. During this time she developed a reputation for refusing to spend money to improve the Reds and complaining about paying for players on the disabled list. In the 1990s, Schott developed a reputation for making racist and anti-Semitic remarks, sometimes towards her own players. Eventually she was removed from having a role in team management after making comments supporting Adolph Hitler and the Nazi party.

12 Mike Brown – Cincinnati Bengals

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Mike Brown is the son of football legend Paul Brown, but few of his father’s skills and acumen have trickled down to him. Brown currently serves as the owner, president, and general manager of the Cincinnati Bengals. Brown has threatened to move the franchise if they were not given a new stadium. He has continuously employed unsuccessful and misbehaving players throughout his tenure, to the detriment of his team. He remains one of the most frugal owners in a league with skyrocketing, tax exempt profits.

11 Peter Pocklington – Edmonton Oilers

via sportsnet.ca

During his tenure as the owner of the Edmonton Oilers, Peter Pocklington made the mistake of trading the greatest player in NHL history. Pocklington has repeatedly defended the Wayne Gretzky trade, and said on numerous occasions that he would do it again. A series of poor investments and running the team on credit caused him to eventually sell it. Pocklington was eventually forced to declare bankruptcy and currently faces prison time on perjury charges. His case is currently still in the appeals process.

10 Jim Irsay – Indianapolis Colts

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In March, Jim Irsay was stopped by police who determined he had been driving while under the influence of alcohol. Irsay was also found to be in possession on prescription pain medication and has been described as having an ongoing substance abuse problem. These offenses caused the NFL to suspend him for the first six games of this NFL season and fine him $250,000. Irsay also lost his driver’s license and must submit to drug testing.

9 Wayne Huizenga – Miami Dolphins, Florida Marlins, Florida Panthers

Steve Mitchell-USA TODAY Sports

After the Florida Marlins won the 1997 World Series, owner Wayne Huizenga immediately began dismantling the team in one of the biggest “fire sales” in sports history. The Marlins mounted one of the worst title defenses in sports history, and Huizenga sold the team the following season. Huizenga has since sold off most of his stake in the franchises and currently only owns 5% of the Dolphins and 5% of the Sun Life Stadium. Huizenga did manage to turn nearly a $1 billion profit on his sale of the Dolphins in 2009.

8 Harold Ballard – Toronto Maple Leafs

via thestar.com

Harold Ballard is one of the most notorious owners in NHL history. Ballard acquired the Maple Leafs as part of a group involving Stafford Smythe, whose father Conn Smythe was the previous owner. Ballard focused almost exclusively on the business side of the team, and once used a fire axe to negotiate a broadcasting agreement with the Canadian Broadcast Corporation. Shortly after taking control of the team, Ballard faced 49 charges of tax evasion, fraud, and theft and eventually served one year in federal prison.

7 Mohamed Al-Fayed – Fulham FC

via tipsfotball.com

Mohamed Al-Fayed purchased Fulham Football Club for only £6.25 million in 1997. Two years later Michael Jackson attended a league game featuring Fulham taking on Wigan Athletic. Al-Fayed succeeded in making Fulham a Premier League mainstay during his tenure as owner. In 2011, a statue was unveiled outside Craven Cottage depicting the famous singer, which was a little bit insane...

In 2013, Al-Fayed sold the club to American businessman Shadid Khan, who promptly had the statue removed. Al-Fayed has blamed the team’s subsequent poor form and relegation on bad luck resulting from the removal of the statue. Even more insane...

6 Vincent Tan – Cardiff City

via theguardian.com

In May 2010, Vincent Tan led a Malaysian consortium that purchased Cardiff City football club. He almost immediately rebranded the club from blue to red and installed a dragon on the club badge. The club found success in the Championship and were promoted to the Premier League for the 2013-14 season. Tan stressed that the club should purchase players with 8’s in their birthdays, which was complied with when the club signed Magnus Wolf Eikrem, who was born on August 8, 1990.

5 Bill Veeck – Cleveland Indians, Chicago White Sox, St. Louis Browns

via sports.mearsonlineauctions.com

Bill Veeck is a maverick baseball owner that is credited with integrating the American League and being known as the last baseball owner to purchase a team without holding an independent fortune. He also engaged in a number of publicity stunts in order to promote his teams, including playing 3’7’’ Eddie Gaedel, holding “Grandstand Managers Day,” the league’s first exploding score board, and the dreaded “Disco Demolition Night.” Throughout his career, he maintained an open door policy with players and fans alike, who could reach him by calling the Comiskey Park switchboard and asking for Bill Veeck.

4 Jerry Jones – Dallas Cowboys

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Jerry Jones continues to operate the Dallas Cowboys as owner, president, and general manager despite ongoing criticism from the public. He has publicly feuded with former coaches including Super Bowl winner Jimmie Johnson, whom he hired after firing the iconic Tom Landry. He has been fined multiple times by the NFL for offenses such as criticizing officials and violating a league wide gag order regarding labor negotiations. Jones has a penchant for Johnnie Walker Blue, which may explain some racy pictures which made their way to the internet in recent weeks.

3 Mark Cuban – Dallas Mavericks

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Over the course of his ownership of the Dallas Mavericks, Mark Cuban has attracted an extraordinary amount of attention for violating league policies. He has publicly criticized officials, yelled at players from courtside seats, and even ran onto the court during a brawl. He was also involved in an April Fools prank, where he pretended to attack an NBA referee. Cuban has also expressed interest in becoming the owner of the Pittsburgh Penguins and Chicago Cubs, but both deals have fallen through.

2 George Steinbrenner - New York Yankees

via cleveland.com

George Steinbrenner has been such a hands on, domineering owner that he inspired the caricature of himself that was portrayed on Seinfeld. The Boss had a reputation for hiring and firing managers on a whim, demonstrated by his hiring and firing of manager Billy Martin five times. Steinbrenner also paid a gambler to find incriminating evidence against Yankee superstar Dave Winfield. He was permanently banned from day-to-day management of the club, but was reinstated in 1993. He is honored with a monument in Monument Park in Yankee Stadium.

1 Al Davis – Oakland Raiders

via newyork.cbslocal.com

Al Davis lived by the credo “Just Win, Baby.” Throughout his ownership of the Raiders his teams have fluctuated between winning and losing. He traded head coach Jon Gruden, benched Marcus Allen following a contract dispute, and drafted a kicker in the first round. He also hired and fired the first African-American coach in NFL history. Al Davis had a reputation for battling with the league in court and had a notorious rivalry with former NFL Commissioner Pete Rosell. The Raiders also would abstain from all league votes, as they continue to do with his son as owner, which is another way that Davis would rebel from the league he helped merge with the AFL, Late in his life, the Raiders suffered through many losing seasons, but Davis’ passion for the game and involvement remained.

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