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


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.

Disneyland News Today

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).