These Sports Owners Made Mistakes Even Their Billions Couldn’t Hide

Darren - December 15, 2022

These Sports Owners Made Mistakes Even Their Billions Couldn’t Hide

Darren - December 15, 2022

Sports fans love their teams more than anything else in the world. However, they can’t control who buys their famous franchise or club. Many of these billionaires made mistakes that their vast resources couldn’t hide. In the end, the fans suffer because they don’t enjoy the product they’re watching.

Sometimes the owner thinks they’re making the right decision but it goes badly wrong. Maybe they draft the wrong player or fire a good coach. Often, they have a messiah complex and override expert advice. Then the team plummets downhill because they didn’t know what they were doing.

Oregon Live

Dean Spanos

Spanos owns the Chargers and infamously moved them from San Diego to L.A. This made him a massively unpopular figure because the former city loved their team. But the city government refused to sanction a new stadium and Spanos snatched them away. He then made many more high-profile mistakes that hurt the franchise.

Wealth Management

He traded Drew Brees to the Saints and signed Philip Rivers instead. The latter had a decent career and was a loyal servant to the franchise, but he was not the same class of player. Furthermore, he fired Marty Schottenheimer after a 14-2 season. We’ve no idea what he was thinking there but it was a garbage decision (via

Miami Herald

Stephen Ross

The Dolphins owner became a massively controversial figure in 2022 after he fired Brian Flores. The former head coach filed a lawsuit against his former boss. He alleged that Miami tried to pay him to throw games and tank the season. Flores’s pride prevented him from doing this and he paid the price.


Also, an NFL investigation revealed that Ross and his minions attempted to tap up Tom Brady. They also approached Sean Payton illegally when he was working for the Saints. In the end, they lost their first-round draft pick and the key actors received fines for their shady antics (via Bloomberg).

New York Times

Steve Cohen

The New York Mets operate under the shadow of their city rivals but Cohen isn’t making their lives easier. The franchise owner promised World Series titles when he bought the team but this may be far away. Mets fans greeted him with excitement because they thought a massive change was around the corner (via New York Post).


When things went wrong, Cohen preached patience before he had a public temper tantrum. Furthermore, the team is dysfunctional behind the scenes with player petulance rising to the fore. It didn’t help that police arrested the assistant GM for sexual harassment. Maybe buying the Mets was Cohen’s biggest mistake.


Jerry Jones

Jones is one of the most polarizing sports franchise owners in the world today. He deserves some credit for maintaining the Cowboys as the most popular sports team in the U.S. This is despite the reality that they haven’t won a Super Bowl for decades. But there is no pretending that he hasn’t made mistakes despite his pouring billions into the team.


Many of these involved dubious coaching hires. One of the worst of these saw him dedicate too much time to Jason Garrett. This was a terrible error that held the franchise back for several years. Meanwhile, Jones makes many comments that land him in hot water. These included unfortunate racially-charged remarks that nobody wants to hear (via Bleacher Report).

Shark Tank

Mark Cuban

Cuban is one of the most visible owners in the NBA today but he polarizes fans. That’s because he made mistakes that people can’t understand. One of these saw him shake hands with DeAndre Jordan after apparently signing him for the franchise. But Jordan didn’t sign anything and rejoined the Clippers (via The Sports Rush).


Meanwhile, Cuban refused to pay Steve Nash and lost the star point guard to the Phoenix Suns. It was a terrible decision but Cuban didn’t want to break the bank. Furthermore, Cuban’s personality grates many basketball lovers because he wants everybody to like him. Inevitably this means that many of them don’t want to hear about him.


Mike Brown

It may seem strange to include Brown on this list. The team made a rare Super Bowl appearance and the future is bright with Joe Burrow at quarterback. But this doesn’t hide the reality that Brown made mistakes throughout his reign. He infamously lied about firing Sam Wyche and claimed that the coach resigned.

Sporting News

If this didn’t endear him to the fanbase nor did the lack of investment in the team. Brown’s tight-fisted nature became the source of many Bengals fans’ frustration. They wanted to compete in the AFC but it felt like they were making up the numbers. Finally, they became so bad that they drafted good young players. Maybe Brown was a genius after all (via NPR).

The Telegraph

Evangelos Marinakis

Many Nottingham Forest fans love Marinakis because the team returned to the Premier League under his guidance. This came after two decades in the wilderness so it’s not a surprise that they love him. But he made mistakes that money failed to hide when they went up to the next division.

In Time Sports

Forest went on a ludicrous spending spree that saw them sign almost 30 players as they rebuilt the team. However, manager Steve Cooper struggled to identify his best starting team. They struggled on the field before Marinakis fired his recruitment team. It was an embarrassing sequence of events for the Greek owner (via Nottingham Post).

Boston Globe

James Dolan

It’s not easy to be a Knicks fan because Dolan is one of the most toxic owners in sports. His relationship with the media is notorious because he treats them like dirt. The Knicks had the worst record in the league this century because of his inept leadership. Top players didn’t want to perform for them because of his dysfunctional nature (via Bloomberg).

New York Times

Arguably the worst thing he ever did was make Isiah Thomas Director of Basketball Operations. Thomas turned the team into an atrocious mess and they descended into chaos. Meanwhile, Dolan handed out terrible contracts and made bad trades like the one for Eddy Curry. In sum, the man is a complete disaster and his money can’t hide that.


Roman Abramovich

Abramovich signaled a new dawn for the Premier League when he bought Chelsea in 2003. The controversial Russian oligarch transformed the club and made them a global force. They won many titles with the money that he earned from the energy industry and signed world-class players.

Vanity Fair

But his reign came to a crashing end after Russia invaded Ukraine. Abramovich’s mistake was his close relationship with Vladimir Putin. His failure to separate politics from business cost him his team because he became a global pariah. Now he’s a persona non grata in Europe (via Jersey Evening Post).

Front Office Sports

John Fisher

Fisher is one of the most controversial owners in MLB today. The hotel chain owner’s fortune is worth billions of dollars but the Oakland A’s don’t see it. He notoriously doesn’t spend a lot of money on the franchise. Now there’s a risk that they will become the second Oakland franchise to move to Las Vegas.

San Francisco Chronicle

One of the biggest mistakes that Fisher made was refusing to connect with the fanbase. He operates in the shadows and most of his top employees didn’t meet him until 2019. Some people like that he doesn’t make everything about him. But others wish that he had more of a hand in the franchise’s operations (via Sports Illustrated).

Sky Sports

Joseph Tsai

Tsai is a big proponent of equality and civil rights in the U.S. He regularly donates vast sums of money to causes across the nation. However, he also made mistakes that his money can’t hide. That’s because his philanthropy doesn’t apply to China. Many people think that he’s a hypocrite because of his association with the Chinese state.

New York Times

The entrepreneur collaborates with blacklisted companies in China despite global condemnation. They engage in mass surveillance and have no regard for human rights. It’s bizarre that Tsai’s humanitarian spirit only applies to the U.S. but the Nets owner thinks he has the moral high ground (via Deadspin).

New York Times

Vincent Viola

Viola owns the Florida Panthers with moderate success. He also enjoyed a relatively decent profile off the field because the team improved inclusivity off the ice. But he made mistakes away from hockey that damaged his reputation. Donald Trump picked Viola as his nominee for Army Secretary.

Miami Herald

But he didn’t land the gig because of his blatant corruption. Viola manipulated stock to buy government contracts before he took his job. Lawsuits emerged and made it impossible for Trump to install Viola in the role. It’s safe to say that this wasn’t the smartest move that the Panthers owner ever made (via Bloomberg).

Sky Sports

Stan Kroenke

Many people think that Kroenke represents the worst of the NFL because he transplanted the franchise from one city to another. He moved the Rams from his native state of Missouri to Los Angeles. Many people think this was a mistake because Californians have an ambivalent relationship with the team.


In 2021, the Rams won the Super Bowl with a victory over the Cincinnati Bengals. But this short-term victory came at a cost after they spent a fortune on assembling an all-star roster. The Rams immediately suffered a massive decline in 2022 and will soon struggle to cope with the damage to their cap space (via The Nation).

Sports Illustrated

Arturo Moreno

Angels fans thought it was good news when Moreno bought the franchise in 2003. He became the first Latino MLB owner in history and appeared to be a baseball fan too. But it all went downhill from there because he ran the team into the ground. Moreno ignored scouts and paid massive contracts for underperforming athletes.


Then the team found itself with two of the most exciting players in MLB. We’re talking about Shohei Ohtani and Mike Trout but Moreno refused to surround them with talent. Trout only made a single postseason foray in his career and this is scandalous. He’s one of the worst owners ever (via L.A. Times).

Jerry Richardson

Richardson was an NFL legend before he single-handled destroyed his reputation. The former Panthers owner sexually harrassed many of his female employees and this made his position with the franchise untenable. First, it’s not true to say that it was a mistake because he intended to commit these disgusting acts.


But it was a terrible error of judgment to bring this vile behavior to the workplace. Nobody knows what he was thinking because he was in a position of power. It was likely that somebody would file charges against him eventually. In the end, he paid the price for his disgraceful antics and abuse of authority (via Forbes).


Bob Nutting

Some billionaires want their franchises to win and be the best in the league. Others treat their team as an ornament and enjoy the prestige of owning it. They don’t care if it’s not successful as long as it belongs to them. That’s precisely the situation with Nutting and the Pittsburgh Pirates.

Pittsburgh Post-Gazette

He infamously took a picture with a fan in 2021. But he didn’t realize that the supporter wore a t-shirt that said ‘Sell the Team.’ This humiliated the billionaire but he earned this because he is a garbage owner. Nutting doesn’t invest in the team and made the Pirates one of the most pointless in the nation (via


Mark Davis

Money motivates Davis more than anything else in this world. It’s safe to say that he doesn’t make mistakes as regularly as his late father, Al. But he occasionally produces a dramatic gaffe and we’re not just talking about that dubious haircut. Some fans think moving the Raiders to Las Vegas was an error but that’s a polarizing opinion.

Bleacher Report

The biggest issue that people have with Davis is the way he handled the Jon Gruden situation. Gruden was at the center of a disgraceful email scandal that saw him lose his job. But Davis acted as though he had no idea that Gruden was a horrible person. Winning mattered more than character but the Raiders didn’t even do that (via Yardbreaker).


Dan Snyder

It’s difficult to know where to start with Snyder because he is one of the worst owners in sports history. He made mistakes with his business and in his social dealings. Let’s start with the former because he tried to pour millions into the team. However, he made misplaced trades and signings that didn’t help Washington (via The Athletic).


Remember when he gave Albert Haynesworth $100 million? This was one of the worst errors of his tenure because Haynesworth immediately stopped trying. He cruised through the remainder of his NFL career because he didn’t care anymore. Meanwhile, the recent decision to sign Carson Wentz was also terrible. Recently, his workplace harassment scandal, financial dealings controversies, and Congressional Oversight Committee investigation have Snyder on the edge of selling the team.

New York Times

Silvio Berlusconi

Berlusconi is one of the sleaziest politicians in Europe but he doesn’t care what people think about him. He loves soccer and transformed A.C. Milan into one of the continent’s most dominant teams. But it fell apart after his legal problems arose. He became embroiled in a corruption case and received a criminal conviction.


Then there was the notorious Rubygate and the Bunga Bunga parties. He allegedly propositioned minors for sexual acts at these exclusive social events. In the end, it became untenable for him to lead Milan despite his millions. The former Italian Primer Minister shamelessly reentered politics after his legal woes ended (via France 24).

Vanity Fair

Michael Jordan

Many people think that Jordan is the greatest NBA player in history. He became a serial winner with the Chicago Bulls as well as the world’s most popular athlete. Furthermore, he became the first former NBA player to buy a league franchise. Jordan obtained the Chicago Hornets in 2010 (via Sporting News).


Unfortunately, this story doesn’t have a happy ending because Jordan is a terrible owner. Charlotte is arguably the most pointless franchise in the NBA and never competes. They rarely produce All-Star talent and show no ambition. It’s not surprising that Jordan wanted to remain in the sport but he hasn’t helped the Hornets.


Woody Johnson

The Jets finally had a decent season in 2022 after they punished their fans for a decade. This came after their owner made mistakes like a factory produces cell phones. It’s difficult to know where to begin because there were so many terrible decisions. He learned that nobody should listen to Peyton Manning’s advice about coaches.

New York Post

Manning described Adam Gase as a ‘quarterbacks guru’ and advised Johnson to appoint him as head coach. Johnson took this on board and hired Gase. But the team immediately descended into chaos and Gase destroyed top draft pick QB Sam Darnold. Remember this is a snapshot of Johnson’s reign because he made many terrible calls (via The Guardian).


Stan Kroenke

Kroenke appeared on this list previously and also owns Arsenal F.C. in the English Premier League. However, he has a mixed relationship with fans because he made mistakes that damaged the club’s prospects. In 2006, he finished building a new stadium for the club. But this meant that they didn’t have the money to compete with their rivals.


It was 2022 before they became a genuine contender again. Also, Kroenke failed to plan for the departure of long-serving manager Arsene Wenger. This was a terrible miscalculation because nothing lasts forever. It had a shocking impact on their fortunes because of the transition (via The Mirror).


Dan Gilbert

According to Forbes, Gilbert is one of the 25 richest people on the planet. However, this means there’s no excuse for the way that he treated LeBron James. He had the best player in the world on his roster but refused to support him. This was a terrible mistake because James lost patience with the franchise.

Bleacher Report

He loves Cleveland and his native Akron more than anywhere else. But he also wanted to win rings and that’s why he made the infamous decision to join Miami. Then Gilbert launched a venomous rant about the player. This was ridiculous because he created the circumstances that forced James to leave (via ESPN).

Liverpool Echo

John Henry

Henry is one of the most successful Massachusetts businessmen ever. He owns the Boston Red Sox and Liverpool F.C. Both of these teams experienced glory under his charge but he also made mistakes. Many Liverpool fans have mixed feelings about Henry because they don’t trust his intentions (via The Mirror).

Sky Sports

One of his mistakes saw him attempt to trademark the name ‘Liverpool.’ In the end, a court ruled against this but it damaged his image in the U.K. He also supported the creation of a new European Super League. This brought immense criticism from fans who accused him of ripping the club’s history apart.

Florida Times-Union

Shad Khan

The Jacksonville Jaguars is a strange franchise for several reasons. They don’t enjoy much success on the field but they also have a small fanbase. Their owner Khan made mistakes that hurt them too. 2021 began in a promising way after drafting a generational talent in Trevor Lawrence (via Sports Illustrated).


But then Khan appointed Urban Meyer as the team’s head coach. This saw them experience one disaster after another as Meyer burnt the house down. He made a series of insane decisions and brought the negative press to the franchise. Meyer danced with younger women, appointed a racist fitness coach, and infuriated his players, kicking one of them before finally getting handed his papers.


Ricketts Family

Chelsea fans heard that the Ricketts family wanted to buy their club. They immediately protested because they saw how the Ricketts ruined the Chicago Cubs. Somehow they turned the best team in MLB into one of the worst in the league. This was almost an amazing achievement in itself.

Chicago Tribune

This also forced Rob Manfred to deny that baseball teams engage in tanking. Most people think that the Ricketts family is stupid and inept. They suffer from the billionaire syndrome that prevents them from listening to experts. Instead, they make dumb decisions that hurt their fanbase (via NBC Sports).

New York Times

David Glass

It was amazing when the Kansas City Royals won the World Series in 2015. Nobody expected this because their owner failed to invest in the franchise. He stuck to a tight salary cap because he didn’t want to compete with the big spenders. Meanwhile, he advocated this approach across the league.


This made their 2015 victory an anomaly that he tried to use to validate his approach. Some people argue that it’s not wrong to want to maintain a sustainable approach. But there’s a difference between this and being tight-fisted. This is also why Bengals fans resent Mike Brown (via The Athletic).


DeVos Family

The DeVos family owns the Orlando Magic NBA franchise but many fans hate them. That’s because they infamously treat homosexual people with contempt. It’s not a good idea to alienate a significant chunk of a fanbase but it doesn’t bother them. Perhaps they don’t care about the revenue that they’re losing.

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But they don’t advertise the franchise well either. It’s not easy for the Magic to compete with the Miami Heat but they don’t even try. There are no promotions outside of the city so the franchise can’t grow. This means that it’s a weird enterprise and nobody understands their thinking (via Fansided).


Robert Kraft

The Patriots are the most successful NFL team of the 21st century. Kraft is one of the winningest owners on this list but that doesn’t mean he hasn’t made mistakes. Some people think allowing Tom Brady to leave the franchise was an error. But this isn’t the biggest issue that Kraft created.


No, we’re talking about his ridiculous massage parlor incident. Allegedly, Kraft received a happy ending at an Asian massage parlor in Texas. Investigators uncovered the incident but Kraft’s lawyers blocked the video evidence in court. However, he couldn’t stop the damage to his reputation (via Vanity Fair).

The Business Journals

Peter Angelos

It feels like the Orioles don’t want to win games. That’s because Angelos created a losing culture that is continuing. They have a brilliant ballpark but they don’t play well enough to justify it. Angelos made mistakes that nobody understands because they’re so dumb (via Bleacher Report).


Carl Ripken Jr. is an Orioles legend and one of the most experienced baseball men alive. He offered his services as a mentor to the team but Angelos infamously refused. He didn’t want Ripken to receive any credit if the team became successful. It was a shortsighted view because the team didn’t win anything whatsoever.

New York Times

Fred Wilpon

The Wilpons ran the New York Mets into the ground with a bunch of garbage decisions. They made terrible draft picks that failed to help the team and turn them into a contender. Meanwhile, they couldn’t appoint a decent manager or coach if it meant saving their lives. It takes an education to become this inept but they turned it into an art form.


Then there was Wilpon’s business partner Bernie Madoff. The Ponzi scheme leader received a 150-year prison sentence after he defrauded many people. It’s safe to say that Wilpon is a shady individual in sports as well as his regular business life. Mets fans can’t even say that he’s a winner because it’s not true (via NPR).

The Independent

Tom Hicks

Hicks is one of the worst sports owners in history because he made mistakes with every franchise he owned. One of his most infamous decisions saw him commit hundreds of millions to Alex Rodriguez. However, this meant that the Texas Rangers didn’t have enough money to spend on the rest of their roster.

Meanwhile, Liverpool fans loath him because he almost ran the Premier League side into the ground. Hicks and his partner, George Gillette, left the club in debt and in a terrible league position. Then they tried to sue the team after they lost control. It was a disastrous episode and one that sums up Hicks as an owner (via Liverpool Echo).


Charles Wang

Technically, we’re cheating by including the late Wang on this list. But the former Islanders owner was one of the worst in sports history. He made mistakes that money couldn’t hide. However, ironically, his biggest mistake was trying to hide money because he misreported the franchise’s cable earnings (via ESPN).


Some people give Wang credit because he kept the team on Long Island. However, the team remained in rebuilding mode throughout his reign and made no progress on the ice. They made terrible recruitment decisions and he failed to fire GM Mike Milbury. He made mistakes that stalled the franchise’s development.


Jerry Jones

Jones is one of the few owners on this list who earns a couple of entries. One of the main problems with Jones is that he thinks that he knows better than everybody else. Dallas had a phenomenal opportunity to draft Randy Moss and it made sense. Even his scouts wanted to select the player because they recognized his high ceiling (via Bleacher Report).


But Jones sometimes takes a hands-on approach that damages his team’s prospects. In the end, they drafted Greg Ellis whose main crime was that he wasn’t Moss. Ellis was a defensive end who won the NFL Comeback Player of the Year award. The 12-year veteran also made the Pro Bowl but he wasn’t on the same level as the all-time great.

NBC Sports

Clayton Bennett and Aubrey McLendon

It’s easy to see why Bennett and McLendon are two of the most unpopular men in Seattle. They bought one of the most iconic NBA franchises before transplanting it to another state. This evil pair snatched the SuperSonics and rebranded them as the Oklahoma City Thunder (via Forbes).

Sky Sports

They fought with the city of Seattle over a new stadium but the politicians refused to budge. Then McLendon made a mistake when he admitted that they didn’t buy the franchise to keep it in the city. Before this, they pretended that it was Seattle’s fault. After this, there was no mistaking their intentions.

The Business Journals

Bruce Sherman

Many people will wonder why Jeffrey Lloria isn’t on this list because he ran the Marlins into the ground. But we opted to include his replacement and the franchise’s current owner, Sherman. That’s because he continued where Lloria left off. After all, he doesn’t want to put money into the team.

San Diego Union-Tribune

The Marlins have one of the lowest attendances in the league and can’t fill their stadium. Meanwhile, their payroll is atrocious and they don’t attract good players. In the end, Sherman is responsible for this. It’s indeed his business but fans argue that he must invest as the franchise’s custodian (via Miami Herald).

Detroit News

The Ford Family

Let’s kick this off by saying that Fords aren’t the most evil owners in the NFL by any stretch of the imagination. But they are responsible for decades of inept management and this is why many fans hate them. Sheila Ford Hamp indeed appears to be taking the franchise in a more positive direction.

Canton Repository

But the team endured years of suffering because of terrible coaching hires and poor decisions. It’s remarkable how unsuccessful the Lions have been despite their prominence in the region. The Motor City deserves better but the Fords held them back. Hopefully, much more improvement is around the corner (via CBS News).

Bleacher Report

Dan Snyder

We’ve already discussed Snyder’s personnel mistakes but he also made many shocking ethical decisions. One of the worst saw him refuse to rename the team. He defied critics by retaining the old ‘Redskins’ nickname until advertisers threatened to withdraw. Then he finally gave in because he didn’t want to lose money from his sponsors.

Front Office Sports

Furthermore, a New York Times report revealed the franchise’s toxic workplace culture. Several cheerleaders complained about sexual harassment. They also blamed Snyder for encouraging this dubious workplace environment. This story took a very dark turn and this directly affected his ownership (via SBNation).


The Glazers

The Glazers won the Tampa Bay Buccaneers and their team won a Super Bowl in 2020. This was a phenomenal achievement for the franchise but fans don’t universally love them. They also own Manchester United but made mistakes that they can’t hide. United fans loathe the family because they’re running the team into the ground.


They try to throw millions of dollars at problems but they don’t have a clear plan about anything. This means that the club has many overpaid and unmotivated players. Furthermore, the stadium is deteriorating because they haven’t invested in it. This makes many fans hate them a lot (via The Athletic).

Sporting News

Jimmy Haslam

Haslam is the king of truck stops across the United States. He also owns the Cleveland Browns as well as the Columbus Crew. This makes him the most significant and influential sports franchise owner in Ohio. But he makes mistakes like they’re going out of fashion. Haslam believed that Johnny Manziel was the future star of the tortured franchise.

San Diego Union-Tribune

Then he alienated many fans when he handed a massive contract to DeShaun Watson. This was massively polarizing because of Watson’s ongoing legal case. Many fans didn’t want to follow a team whose star player sexually harassed women. Haslam thought that his billions would make them forget but he was wrong (via New York Post).