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Top 10 Chuckleheads Who Made a Sh!tload of Money in Sports

Updated: Feb 22, 2021

At the end of the day, sports is a business. Toss out win/loss records, these 10 made hundreds of millions of dollars in profit and were not considered the sharpest tools in the shed when it comes to sports.

10. Howard Schultz

In 2001, Starbucks CEO Howard Schultz bought the Seattle Supersonics for $200 million. Within 5 years, Schultz soured on actually running an NBA franchise because the city of Seattle wouldn't build him a shiny new billion-dollar basketball play toy. In 2006, Schultz sold the team to Professional Basketball Club, LLC, in Oklahoma City. (Why do guys in Oklahoma want to buy a team whose city won't build them a stadium? Hmmm?) In 5 short years, the sale price of the Supersonics shot up $150 million, while the city of Seattle was screwed out of their basketball team two short years after the sale. The city of Seattle was awarded $75 million in compensation from PBC LLC (over 2 payments), but it was Judas Schultz who made the most money on the deal. And don't forget, Schultz continues to rob you, the reader, every time you wait in line at Starbucks for a $5 cup of coffee.

9. Chris Webber

Believe it or not, Chris Webber made nearly $180 million in career salary in the NBA. He makes this list because he also made over $200,000 in his 2 years at Michigan as part of that school's legendary Fab Five. Losing the Championship at Michigan in 1993 due to his famous non-existent timeout was actually the highlight of his playoff career.

Don't get me wrong, the first part of his NBA career was borderline Hall-of-Fame worthy, but after microsurgery, he wasn't the same player. Seeing him on the TNT broadcasts doesn't help our opinion here at all. Seriously, playing word association, when I say Chris Webber, do you think Sacramento King great? Or do you think of the Timeout and almost causing Michigan to get the Death Penalty in college basketball.

8. Roger Goodell

Roger Goodell became NFL Commissioner in 2006 and his first order of business was to Protect the Shield. Does that mean player safety? No, he fought tooth and nail against early concussion studies. Does that mean player's rights? No, the NFL has the weakest players union of all of the major sports. When was the last time Goodell circumvented the collective bargaining agreement in FAVOR of a player? Does Protecting the Shield mean doing anything possible to protect the owner's profits? Yes it does.

As, arguably, the biggest punching bag in all of sports management, booed by fans at the draft, at games, and at trophy presentations, Goodell has earned over $200 million in just over 10 years protecting the interests of Billionaires. (Note: Graph above is updated to the 2014-15 Season.)

If you google Roger Goodell Memes, you'll be surprised how many really funny ones pop up.

7. Charles Wang

From 1980 to 1983, the New York Islanders were the best team in the NHL. In the mid-eighties, long-time owner John Pickett decided he wanted to be an absentee owner and moved to Florida and simply cash Islander checks. This went on for about 10 years before he decided to sell the team to convicted shyster John Spano in 1996. In under a year, Spano almost killed the Islanders and his deceit was so deep and far-reaching that he spent over 5 years in jail in relation to his ownership tenure. Out of the ashes of that debacle came a confusing series of ownership transitions until the Islanders landed in the lap of Charles Wang and Sanjay Kumar for $187 million.

Within 5 years Sanjay Kumar would be in jail and Wang was in sole possession of the Islanders. That left Wang to make curious decisions like firing his GM after a month and a half on the job, then giving Garth Snow a 10 year internship. Decisions were made as a collaborative effort with the hockey people, instead of trusting them to do their own jobs and Wang constantly moaned about his lease for the Nassau Veterans Memorial Coliseum. Not surprisingly, Wang explored moving the Islanders to Quebec City, Kansas City, different boroughs in New York City, and probably suburban Beijing. By the time the lease was up, the Islanders moved to the Barclays Center in Brooklyn (technically still on the Island), and the eccentric Wang cashed in for $485 million AND still got to keep minority ownership with the team.

6. Gund Brothers

George Gund was a minority owner of the California Golden Seals in the NHL when he convinced then owner Mel Swig to move the team to Cleveland in 1977. Re-naming the team the Cleveland Barons, George and Gordon Gund bought the team, then promptly merged the Barons with the Minnesota North Stars and stayed in Minnesota for a decade or so.

The globe-trotting Gunds then tried to move the North Stars back to the San Francisco area, but the NHL wanted a team in hockey-lovin' Minnesota, so the Gunds sold the North Stars to Norm Green in 1990 (who then moved the team to Dallas in 1993) and the Gunds were granted the San Jose Sharks as an expansion team. The restless Gunds then sold the Sharks for $147 million in 2002.

Meanwhile, back in Cleveland, the Gunds had also bought the Cleveland Cavaliers in the NBA in 1983, saving that franchise from the dumpster fire status it had gained under previous owner Ted Stepien. Stepien sold the Cavaliers to George and Gordon Gund for $20 million in 1983, but in yet another sweetheart deal from a league, N.B.A. owners awarded the Cavs bonus first-round picks for each year from 1983-86 to help compensate for the ones Stepien traded away.

The Gunds replacing Stepien as owners was like going from an F on your report card to a D+. In the mid 90's, the Cavs (and the Indians) threatened to move unless they got new stadium deals and in 1994 Gund Arena opened. Sadly, by 2002, the Cavs were the worst team in the NBA again. Luckily for Cleveland, even the Gunds couldn't mess up the first pick in the 2003 draft and the Cavs struck gold by drafting straight-outta-high schooler LeBron James. Then, the next year, Gordon Gund got Jedi mind tricked by Carlos Boozer and his agent Rob Pelinka and almost immediately put the team up for sale and it was quickly sold for $375 million to Dan Gilbert.

Let's do some quick math, shall we.


+ 147,000,000

Over a Half a Billion Dollars for the Gunds playing musical franchises!

5. Joe and Gavin Maloof

In 1999, Joe and Gavin Maloof were minority owners in the Sacramento Kings and ponied up some family money and inherited some debt and made the Kings a powerhouse on the court. Well, for about 3 years.

Then the Maloofs threatened to move to Virginia Beach, demanded a new arena, threatened to move to Anaheim, demanded a new arena, threatened to move to Seattle, stopped talking to the Sacramento City government, (some of this is out of order, but you get the idea), bitched that the highest bidder wouldn't be from Sacramento, then the league stepped in and stopped the Maloofs from moving to Seattle as they threatened to sue everyone and vowed to move the team again. Then, almost magically, the Maloofs sold the Kings for a then NBA record $535 million to software magnate Vivek Ranadive, who, with a commitment from mayor Kevin Johnson, are keeping the Kings in Sacramento.

4. Art Modell

Art bought the Cleveland Browns in 1961 for $4 million. Well, $250,000 of his own money, a loan and a handful of minority investors. Once in charge, Art Modell fired one of the greatest coaches in the history of the NFL, Paul Brown, Hall of Famer and winner of 4 AAFL Championships and 3 NFL Championships and promptly led the Cleveland Browns Super Bowls and 30-some years of mediocrity. With a love/hate relationship with the city souring by the day, in 1996 Art owned a team that was hemorrhaging money when others in the league were making money hand over fist. Modell announced he was moving the team to Baltimore and then fired probably the greatest coach in the modern-era, Bill Belichick in order to build a winner in his new city. In the year 2000, Steve Bisciotti paid Art $275 million to become the minority owner and then $325 Million more in 2004 to wrestle full control of the Ravens from Modell. Because Uncle Art stuck around the NFL for over 40 years, some want to put him in the Football Hall of Fame. I don't think so. Your reward was $600 million (+ all the perks that the city of Baltimore gave you that even today haven't been fully disclosed). I hope it was worth it to burn all those bridges in Cleveland so you could line your casket with $100 bills.

3. Randy Lerner

In 1999, the expansion Cleveland Browns were awarded to Al Lerner. The same Al Lerner who stood next to his friend Art Modell as he moved the team to Baltimore in 1996. Once gone, Al and Art had a falling out and 4 years and $530 million dollars later Al Lerner was the new sheriff in town. Sadly, Al died in 2002, leaving the Browns to his son Randy. Randy, who ran the expansion Browns straight into the ground and had numerous quirky habits, like not talking to the media if any recording devices were present, wasn't in it to win it. Randy, who inherited a football team in blue-collar Cleveland, then ran out and bought a Premier League team in England because soccer was his passion. Randy, who once delegated his ownership duties to Mike Holmgren, was tired of the perennial losing in the NFL and sold the Browns for $1.1 BILLION after 10 years of "custodianship."

(Karma did catch up to Randy. Historical powerhouse Aston Villa was relegated in 2016 and Lerner was forced to sell with an estimated half a billion dollar loss. Whereas the NFL is a collection of billionaires experimenting in socialism, the Premier League is sports capitalism in its truest form.)

2. Jeffrey Loria

Scumbag Jeffrey Loria didn't scam Major League baseball once, but twice. Once hailed as the savior of the Montreal Expos, he quickly tired of Canada after a short burst of spending and started to explore moving the franchise looking for a quick payday. After setting records for low attendance, Major League Baseball acted to contract 2 teams, the Montreal Expos and the Minnesota Twins. Only an American Court saved the Expos as Jeffrey Loria sold the team back to the League for $120 million, after purchasing them for $16 million, less than 5 years earlier.

Inexplicably, Major League Baseball gave Loria nearly a $40 million interest free loan to help buy the Florida Marlins as the Expos ended up moving to Washington D.C. The price for the Marlins was just over $150 million and for 15 years Loria ran that team into the ground, near the league bottom in payroll, attendance, and record nearly every year of his tenure. Loria jammed South Florida into buiding him a half a billion dollar ballpark that was mired in lawsuits and changed the name of the team to the Miami Marlins when the new ballpark was opened in 2012. This week there are rumors that Loria is selling the team for $1.6 billion to an anonymous New York investor.

1. Frank McCourt

In 2004, Frank McCourt used some creative use of debt and some fuzzy accounting to come up with the $430 million asking price for Major League Baseball's L.A. Dodgers. Almost immediately, he began to gouge his own fans to recoup some of his expenses. Over the next five years, the Dodgers experienced some decent on the field success, but then came 2009.

During the Dodgers' 2009 playoff run, Frank and Jamie McCourt announced their separation, then when the playoffs ended, Frank fired Jamie as the CEO of the Dodgers. Thus began a very public, and very nasty, divorce proceeding. As the court cases dragged on, Frank's already shaky financial holdings collapsed when, in 2011, MLB seized control of the operations of the team as McCourt was forced to declare bankruptcy. Court case after court case after court case ensued until, in the Spring of 2012, Frank McCourt, MLB, and Bankruptcy Court all agreed to allow the sale of the Dodgers to the Guggenheim Group for $2 billion.

After his big windfall, McCourt followed his passion and bought Olympique de Marseille in Ligue 1. (Don't worry Karma fans, around the year 2021, look for McCourt to share the same fate as R. Lerner.)

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