Worst Owners in Sports History

Owning a pro sports franchise doesn’t make you a good person.

Worst Owners in Sports History

New York Knicks owner James Dolan is not a fan of criticism.

The most powerful men and women in sports aren’t the ones you see on the field of play.

Look up in the owner’s box — that’s where the true power resides.

And that hasn’t always been a good thing.

Bad owners show us as much, and they’ve run the gamut when it comes to their transgressions. From convicted criminals to vile racists to unbelievable cheapskates, they’ve all called themselves owners of a pro sports franchise.

These are the worst.

30. The Tribune Company

Wrigley Field — There was little joy in Wrigleyville when the Tribune Company owned the Chicago Cubs.

Teams owned: Chicago Cubs (1981-2009)

Purchase price: $21 million

Sale price: $845 million

Current value: $3.8 billion

Championships won as owner: None

* Note: All stats and data are current through February 2024

Bottom Line: The Tribune Company

The Tribune Company turned a tidy profit on the Cubs, buying the team for $21.5 million in 1981 and selling for $845 million in 2009 — after the Tribune filed for bankruptcy. As owners, it ran the team with complete apathy, as reflected in the record.

Since selling the team, the Chicago Cubs have not only won their first World Series title in over 100 years in 2016 and have tripled in value and are now worth almost $4 billion.

29. Jed York

Teams owned: San Francisco 49ers (1977-present)

Purchase price: $13 million (purchased by grandfather, Ed DeBartolo Sr.)

Current value: $5.2 billion

Championships won as owner: None

Bottom Line: Jed York

Jed York is the definition of being born on second and acting like you hit a double. His grandfather, Edward DeBartolo Sr., purchased the San Francisco 49ers in 1977 and gave the team to his children, Denise and Ed Jr., and Jed is the third generation of DeBartolos/Yorks to own the team.

Jed York was President of the 49ers before stepping down and becoming CEO but his genius move out of the gate was to fire head coach Jim Harbaugh in favor of defensive line coach Jim Tomsula following the 2014 season, which kicked off a 17-47 stretch for the franchise over the next three seasons.

While Jed York's competence as a football executive is in question, his team's financial acumen is not. While his grandfather paid $13 million for the team in 1977, they are now worth an estimated $5.2 billion.

28. Jerry Reinsdorf

Teams owned: Chicago White Sox (1981-present), Chicago Bulls (1985-present)

Purchase price (White Sox): $19 million

Current value (White Sox): $1.65 billion

Purchase price (Bulls): $9.2 million

Current value (Bulls): $4.1 billion

Championships won as owner: 7 (6 with Chicago Bulls; 1991, 1992, 1993, 1996, 1997, 1998 and 1 with Chicago White Sox, 2005)

Bottom Line: Jerry Reinsdorf

Toni Kukoc, Michael Jordan and Jerry Reinsdorf

When it boils down to it, Jerry Reinsdorf's purchases of the Chicago White sox and Chicago Bulls will go down as two of the greatest investments in sports history in regards to purchasing teams.

Reinsdorf purchased the White sox for $19 million in 1981 and four years later purchased the Bulls for a pittance of $9.2 million. By the end of 2022 the White Sox were valued at $1.65 billion and the Bulls at $4.1 billion. So why is he on the list? Reinsdorf and general manager Jerry Krause's treatment of superstar Michael Jordan at the end of his career scares off free agents to this day.

27. Charles Wang

Teams owned: New York Islanders (2001-16)

Purchase price: $190 million

Sale price: $485 million

Current value: $1.02 billion

Championships won as owner: None

Bottom Line: Charles Wang

Charles Wang was in over his head the moment he bought team.

His heart was in the right place, but he was out of touch with the game, as evidenced by his belief that sumo wrestlers would be better goalies than ones that were available.

"I wish I’d never bought the team," he told ESPN in 2009. Wang died in 2018, at 74 years old.

26. Charles Comiskey

Teams owned: Chicago White Sox (1900-31)

Purchase price: $750,000 (to build Comiskey Park)

Sale price: Unknown

Current value: $1.65 billion

Championships won as owner: 2 (1906, 1917)

Bottom Line: Charles Comiskey

When you treat your players like Comiskey did — grossly underpay them, make them wash their own jerseys, send them a case of flat champagne after winning a pennant — you end up with problems.

Like eight players fixing the 1919 World Series in the infamous "Black Sox" scandal.

25. Dean Spanos

Teams owned: San Diego/Los Angeles Chargers (1984-present)

Purchase price: $98 million

Current value: $3.88 billion

Championships won as owner: None

Bottom Line: Dean Spanos

Moving the Chargers from San Diego to Los Angeles will always come up first, but it’s not the worst thing Dean Spanos has done as owner — hee once fired head coach Marty Schottenheimer after a 14-2 season.

He also let Hall of Fame quarterback Drew Brees walk out the door in the prime of his career. This is the franchise that 2004 No. 1 overall pick Eli Manning refused to play for as well. They seem cursed.

24. Mike Brown

Teams owned: Cincinnati Bengals (1968-present)

Purchase price: $7.5 million (father's original ownership stake)

Current value: $3 billion

Championships won as owner: None

Bottom Line: Mike Brown

Mike Brown's first move as owner was lying about firing popular coach Sam Wyche, whom Mike Brown said "resigned." The Bengals didn't win a playoff game from 1989 until 2022, with 21 seasons below .500.

But they've seen their value shoot up significantly in the last three years with the addition of quarterback Joe Burrow, who the team will likely have to make the highest-paid player in professional sports in the near future.

23. James Dolan

Teams owned: New York Knicks (1999-present), New York Rangers (1999-present)

Purchase price (Knicks): $600 million (for both teams)

Current value (Knicks): $6.58 billion

Purchase price (Rangers): $600 million (for both teams)

Current value (Rangers): $2.05 billion

Championships won as owner: None

Bottom Line: James Dolan

Former NBA commissioner David Stern told The New York Times in 2007 that the Knicks were not an example of "intelligent management," which was putting it lightly.

Dolan’s financial mistakes will make your head spin, and he spreads it between the Knicks and Rangers evenly.

22. Jeffrey Loria

Teams owned: Miami Marlins (2002-17)

Purchase price: $158.5 million

Sale price: $1.2 billion

Current value: $990 million

Championships won as owner: 1 (2003)

Bottom Line: Jeffrey Loria

How's this for shady? Jeffrey Loria convinced taxpayers in South Florida to pay for a new stadium, then gutted the Marlins' roster to keep payroll around $20 million when the median was $80 million.

He paid $158 million for the team in 2002 and sold it to an investment group that included Derek Jeter and Michael Jordan for $1.2 billion in 2017, although Jeter sold his interest in the team in February 2022.

21. Bill Wirtz

Teams owned: Chicago Blackhawks (1966-2007)

Purchase price: $5-10 million (estimate)

Current value: $1.5 billion

Championships won as owner: None

Bottom Line: Bill Wirtz

All you need to know is that Bill Wirtz was booed at a Blackhawks game honoring him after his death in 2007.

ESPN named the the team the worst franchise in pro sports in 2004, and he would not allow home games to be televised because it was "unfair to people who bought tickets."

The stingy owner died with a net worth of $1.3 billion and his son, Rocky Wirtz, turned the Blackhawks into a winner, taking home three Stanley Cup championships since his father's death.

20. Tom Hicks

Tom Hicks and Ron Washington — Texas Rangers owner Tom Hicks, right, with new Rangers manager Ron Washington in 2006.

Teams owned: Dallas Stars (1995-2011), Texas Rangers (1998-2010)

Purchase price (Rangers): $250 million

Sale price (Rangers): $240 million

Current value (Rangers): $2.05 billion

Purchase price (Stars): $82 million

Sale price (Stars): $240 million

Current value (Stars): $925 million

Championships won as owner: 1 (Dallas Stars, 1999)

Bottom Line: Tom Hicks

The worst contract in baseball history (for owners, at least) was all Tom Hicks, who inked Alex Rodriguez to a 10-year, $250 million deal in 2000.

When the Hicks Sports Group went bankrupt in 2010 and was forced to sell the Dallas Stars and Texas Rangers, Rodriguez was listed as its largest creditor at $25 million owed.

19. Frank McCourt

Teams owned: Los Angeles Dodgers (2004-12)

Purchase price: $430 million

Sale price: $2 billion

Current value: $3.75 billion

Championships won as owner: None

Bottom Line: Frank McCourt

Frank McCourt bought the Dodgers for $430 million in 2004 despite concerns about his finances.Those concerns came into sharper focus when he paid his wife $130 million in a 2011 divorce, the Dodgers filed for bankruptcy and had day-to-day control of the team yanked away by Major League Baseball.

He sold the team for a then-record $2 billion.

18. Donald Trump

Teams owned: New Jersey Generals (1983-85)

Purchase price: $9 million

Sale price: $3.76

Current value: N/A

Championships won as owner: None

Bottom Line: Donald Trump

Donald Trump’s decision to go head-to-head with the NFL by moving USFL games from spring to fall almost single-handedly sank the USFL. As did his testimony in an antitrust lawsuit against the league. Trump's plan all along was to leverage USFL ownership into NFL ownership. Didn’t work.

While he won the lawsuit he was awarded just under $4 in damages.

17. Michael Jordan

Teams owned: Charlotte Bobcats/Hornets (2010-present)

Purchase price: $200 million

Current value: $1.77 billion

Championships won as owner: None

Bottom Line: Michael Jordan

Michael Jordan took charge of basketball operations for the Charlotte Hornets in 2006 and bought a controlling interest of team in 2010. But the greatest talent in basketball history has fallen short of being able to spot talent himself. In 17 years of overseeing selections in the NBA Draft the Hornets have had just two All-Stars, Kemba Walker and LaMelo Ball.

While Jordan hasn't been successful on the court, his business acumen is as sharp as ever. Jordan purchased a 97 percent stake in the Hornets for an estimated $175 million and as of December 2022 the franchise was valued at $1.77 billion.

16. Jim Buss

Teams owned: Los Angeles Lakers (2013-present)

Purchase price: $67.5 million (total price Dr. Jerry Buss paid for Lakers, L.A. Kings and Great Western Forum in 1979)

Current value: $6.4 billion

Championships won as owner: 2020

Bottom Line: Jim Buss

It took 30 years for the Buss family to build the Lakers into one of the most profitable, valuable and well-run franchises in pro sports. It took Jim Buss, one of famed owner Jerry Buss’ children, just a few years to run the team into the ground after he took over day-to-day operations in 2011.

His sister, Jeanie, fired her brother in 2014 although he has retained his ownership stake. The team is worth an estimated $6.4 billion as of January 2023. Dr. Jerry Buss, purchased the Lakers along with the Los Angels Kings and the Great Western Forum for $67.5 million in 1977.

15. Bob Irsay

Teams owned: Baltimore/Indianapolis Colts (1972-97)

Purchase price: $14.5 million

Current value: $3.8 billion

Championships won as owner: None

Bottom Line: Bob Irsay

With the city of Baltimore about to seize control of the team under the pretext of "eminent domain" laws, Bob Irsay packed off to Indy in the middle of the night and blamed media scrutiny.

Colts fans, some of the proudest in the league, woke up one morning, and the team was gone. Was this the first ghosting? His son, Jim Irsay, has owned the team since 1997, and his father's initial investment of $13.5 million in 1972 has ballooned to an estimated $3.8 billion valuation of the Colts in 2023.

14. The Maloofs

Joe and Gavin Maloof — Sacramento Kings owners Joe Maloof, left, and brother Gavin Maloof, in 2011, never found a way to leave California's capital.

Teams owned: Sacramento Kings (1998-2013)

Purchase price: $156 million

Sale price: $534 million

Current value: $2.03 billion

Championships won as owner: None

Bottom Line: The Maloofs

How bad did brothers Gavin and Joe Maloof want to move the Sacramento Kings out of California? They sandbagged every deal put before them to stay and even tried to move the team to Virginia Beach, of all places.

The Kings averaged just over 20 wins in the last five seasons of their ownership, before essentially being forced to sell the team in 2013 when their casino business went belly up.

13. George Shinn

Teams owned: Charlotte/New Orleans Hornets (1987-2010)

Purchase price: $32.5 million

Sale price: $300 milliion

Current value: $1.77 billion

Championships won as owner: None

Bottom Line: George Shinn

George Shinn, a religious zealot, saw his reputation come undone during a sexual assault trial in 1999. Acquitted of the charges but forced to admit to numerous extramarital affairs, Shinn went into hiding until he couldn’t afford to run the team.

He sold it to the NBA for $300 million in 2010, who sold it to a group of investors led by North Carolina native Michael Jordan.

12. Harry Frazee

Harry Frazee and Frank Chance — Boston Red Sox owner Harry Frazee, left, and manager Frank Chance huddle at New York's Yankee Stadium in 1923. Frazee made the deal that sent Babe Ruth from the Red Sox to the Yankees after the 1919 season.

Teams owned: Boston Red Sox (1916-23)

Purchase price: $600,000

Sale price: $1.2 million

Current value: $3.9 billion

Championships won as owner: 1918

Bottom Line: Harry Frazee

Harry Frazee achieved baseball infamy after selling Babe Ruth to the New York Yankees in 1919, starting the "Curse of the Bambino" that saw the Red Sox go from 1918 to 2004 without a World Series title.

He ran the Red Sox into bankruptcy, then sold them for $1.2 million — double what Frazee paid for the team.

11. Jimmy Haslam

Teams owned: Cleveland Browns (2012-present)

Purchase price (Browns): $1 billion

Current value: $3.85 billion

Championships won as owner: None

Bottom Line: Jimmy Haslam

The Browns have been as bad as any team in the history of the NFL since Jimmy Haslam bought them for $1 billion in 2012. They've had one winning season in the decade since and went winless in 2017.

In his other business ventures, Haslam has been just as bad. His company, Pilot Flying J, was found to have ripped off customers to the tune of $56 million in "gas purchase rebates" and paid a $92 million settlement to avoid federal prosecution.

The Haslam family is about to expand its reach in pro sports — a report in February 2023 indicated they were trying to buy a 25 percent stake in the Milwaukee Bucks.

10. Fred Wilpon

New York Mets owner Fred Wilpon leaves federal court in New York in 2012 after settling for $162 million with a trustee representing Bernard Madoff fraud victims.

Teams owned: New York Mets (2002-20)

Purchase price: $471 million

Sale price: $2.4 billion

Current value: $2.65 billion

Championships won as owner: None

Bottom Line: Fred Wilpon

Fred Wilpon was business partners with Ponzi schemer Bernard Madoff, who ripped off investors for an estimated $65 billion and was sentenced to 150 years in prison in 2009. Madoff’s scheming helped Wilpon turn a profit with the Mets for years.

He settled with a Madoff trustee for the fraud victims for $162 million and sold the team to billionaire financier Steve Cohen for $2.4 billion in 2020.

9. George Reynolds

Teams owned: Darlington FC (1999-2004)

Purchase price: $24.1 million (new stadium)

Sale price: Unknown

Current value: Unknown

Championships won as owner: None

Bottom Line: George Reynolds

George Reynolds was a lifelong criminal with convictions for burglary, safecracking and theft dating back to the 1960s.

He built a fortune with a kitchen surfacing company but ran the Darlington Football Club into the ground by paying for a stadium that was too big by half.

He was convicted of tax evasion and a received three-year prison sentence in 2004.

8. Ted Stepien

Teams owned: Cleveland Cavaliers (1980-83)

Purchase price: $6 million

Sale price: $20 million

Current value: $2 billion

Championships won as owner: None

Bottom Line: Ted Stepien

Cleveland Cavaliers owner Ted J. Stepian

You have to pretty awful for the NBA to name a rule after you. After Ted Stepien traded away five consecutive first-round draft picks, the league instituted the "Stepien Rule," stating that teams cannot trade first-rounders in consecutive years.

His other claims to infamy? The NBA froze his trade rights, and he fired three head coaches during the 1981-82 season.

He ended the charade in 1983 and sold the Cavaliers for $20 million.

7. Jerry Richardson

Teams owned: Carolina Panthers (1995-2018)

Purchase price: $200 million

Sale price: $2.2 billion

Current value: $3.6 billion

Championships won as owner: None

Bottom Line: Jerry Richardson

Carolina Panthers owner Jerry Richardson

Jerry Richardson’s legacy, built over 60 years as an NFL player and owner, came undone in 2017 following a Sports Illustrated article that revealed long-term sexual harassment by Richardson against Panthers employees.

He was fined $2.75 million for workplace misconduct and sold the team for $2.2 billion in 2018.

6. John Spano

Teams owned: New York Islanders (1997)

Purchase price: $165 million (never completed)

Sale price: N/A

Current value: $1.02 billion

Championships won as owner: None

Bottom Line: John Spano

John Spano lied about his net worth when buying the Islanders. He said it was $230 million, but in reality, it was $5 million. His checks to buy the team bounced.

He was sentenced to six years in prison for fraud in 2000, four years in 2006, then 10 years for fraud in 2015.

5. Harold Ballard

Teams owned: Toronto Maple Leafs (1971-1990)

Purchase price: $2.3 million (estimate)

Sale price: $75 million

Current value: $2 billion

Championships won as owner: None

Bottom Line: Harold Ballard

Harold Ballard was convicted on 47 counts of fraud, tax evasion and theft shortly after taking control of the Maple Leafs. He served less than three years of his nine-year sentence. Other controversies involved racist and sexist comments.

Famed goaltender Ken Dryden described him best in "The Game," his seminal book: "He was a villain." Ballard died in 1990 and his family sold his stake in the Maple Leafs four years later.

4. Daniel Snyder

Teams owned: Washington Redskins/Washington Football Team/Washington Commanders (1999-present)

Purchase price: $750 million

Current value: $5.9 billion

Championships won as owner: None

Bottom Line: Daniel Snyder

Daniel Snyder’s time as owner of the Redskins has been defined by how awful the team has been and his disastrous free-agent signings. Eight coaches in 17 seasons, two playoff wins (with the last coming in 2005), and he still makes money hand over fist.

What's worse than that? Snyder's involvement in a wide-ranging tale of toxic workplace culture that involved harassment of female employees, ripping off fellow NFL owners on ticket sales and Snyder himself being accused of sexual harassment. It was bad enough it led to Congressional hearings.

3. Robert Sarver

Teams owned: Phoenix Suns (2004-23)

Purchase price: $401 million

Sale price: $4 billion

Current value: $3 billion (estimated)

Championships won as owner: None

Bottom Line: Robert Sarver

Robert Sarver, an Arizona banking magnate, bought the Suns for a then-record $401 million in 2004.Meddling with the team is Sarver's specialty, and he ran off competent coaches and personnel, like Steve Kerr.

None of what Sarver did could compare to the incident that was his final undoing — a wide-ranging workplace harassment case that forced him to sell the team to United Wholesale Mortgage CEO and former Michigan State basketball player Mat Ishbia and his brother Justin Ishbia for a record $4 billion in 2023.

2. Marge Schott

Teams owned: Cincinnati Reds (1984-1999)

Purchase price: $11 million

Sale price: $67 million

Current value: $1.19 billion

Championships won as owner: 1990

Bottom Line: Marge Schott

Marge Schott bought controlling interest of the Reds for $11 million in 1984. She was banned from baseball in 1993, then again from 1996 to 1998 for comments supporting Adolf Hitler.

A noted anti-Semite, she also expressed hate toward Japanese and African-Americans in her time as owner.

She sold the team for $67 million in 1999 and died in 2004.

1. Donald Sterling

Teams owned: San Diego/Los Angeles Clippers (1981-2014)

Purchase price: $13.5 million

Sale price: $2 billion

Current value: $3.9 billion

Championships won as owner: None

Bottom Line: Donald Sterling

Donald Sterling heckled his own players at Clippers games and didn’t have a winning season until his 11th year owning the team. NBA commissioner Adam Silver banned Sterling from the league for life and forced him to sell the team in 2014 after racist comments recorded by his mistress were leaked to the public.

Sterling sold the team to Microsoft co-founder Steve Ballmer for $2 billion.