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)

Record as owner of team: 2,179-2,113 (.507 winning percentage)

Championships won as owner: None

Bottom line: 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.

#29: Jerry Reinsdorf

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

Record as owner of teams: Chicago White Sox (2,978-2,946, ,502 winning percentage), Chicago Bulls (1,483-1,210, .550)

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

Bottom line: Jerry Reinsdorf bought the White Sox and Bulls for a combined $35 million. Today, the value of two franchises is estimated at $4.4 billion, according to Forbes Magazine. This is very good.

To this day, his treatment of Michael Jordan prevents Bulls from signing high-profile free agents. This is very bad.

#28: Charles Wang

Teams owned: New York Islanders (2001-16)

Record as owner of team: 500-468-30 (.501 winning percentage)

Championships won as owner: None

Bottom line: 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.

#27: Charles Comiskey

Teams owned: Chicago White Sox (1900-31)

Record as owner of teams: 2,300-2,262 (.504 winning percentage)

Championships won as owner: 2 (1906, 1917)

Bottom line: 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.

#26: Dean Spanos

Teams owned: San Diego/Los Angeles Chargers (1994-present)

Record as owner of teams: 202-187 (.519 winning percentage)

Championships won as owner: None

Bottom line: Moving 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.

He 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.

#25: Robert Sarver

Teams owned: Phoenix Suns (2004-present)

Record as owner of team: 585-547 (.516 winning percentage)

Championships won as owner: None

Bottom line: 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 has run off competent coaches and personnel, like Steve Kerr.

As a result, the once-proud franchise hasn’t made the playoffs since 2010 or made an impactful draft pick in 14 years.

#24: Mike Brown

Teams owned: Cincinnati Bengals (1991-present)

Record as owner of team: 186-259-3 (.415 winning percentage)

Championships won as owner: None

Bottom line: His first move was lying about firing popular coach Sam Wyche, whom Mike Brown said "resigned."

The Bengals haven’t won a playoff game since 1989, before Brown took over, and have 21 seasons of finishing .500 or below during his tenure.

#23: Daniel Snyder

Teams owned: Washington Redskins (1999-present)

Record as owner of team: 139-180-1 (.435 winning percentage)

Championships won as owner: None

Bottom line: 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.

#22: James Dolan

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

Record as owner of teams: New York Knicks (599-887, .403 winning percentage), New York Rangers (713-682-49, .493)

Championships won as owner: None

Bottom line: 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.

#21: Jeffrey Loria

Teams owned: Miami Marlins (2002-17)

Record as owner of team: 1,166-1,268 (.489 winning percentage)

Championships won as owner: 1 (2003)

Bottom line: 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.

#20: Bill Wirtz

Teams owned: Chicago Blackhawks (1966-2007)

Record as owner of team: 1,515-1,272-746 (.354 winning percentage)

Championships won as owner: None

Bottom line: 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.

#19: 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), Liverpool FC (2007-10)

Record as owner of teams: Dallas Stars (703-400, .637 winning percentage), Texas Rangers (1,337-1,123, .543), Liverpool FC (64-33-17, .561)

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

Bottom line: 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 Stars and Rangers, Rodriguez was listed as its largest creditor at $25 million owed.

#18: Frank McCourt

Teams owned: Los Angeles Dodgers (2004-12)

Record as owner of team: 761-696 (.561 winning percentage)

Championships won as owner: None

Bottom line: He 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 record $2 billion.

#17: Donald Trump

Teams owned: New Jersey Generals (1983-85)

Record as owner of team: 25-11 (.694 winning percentage)

Championships won as owner: None

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

#16: Michael Jordan

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

Record as owner of team: 248-382 (.393 winning percentage)

Championships won as owner: None

Bottom line: 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 is unable to spot talent. The NBA draft has been a minefield for MJ with just one All-Star appearance (Kemba Walker) in 13 years of picks.

#15: Jim Buss

Teams owned: Los Angeles Lakers (2013-present)

Record as owner of team: 126-345 (.267 winning percentage)

Championships won as owner: None

Bottom line: 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 him in 2014, and she now runs the team.

#14: Bob Irsay

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

Record as owner of teams: 156-240 (.396 winning percentage)

Championships won as owner: None

Bottom line: 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. The first ghosting?

#13: 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)

Record as owner of team: 582-600 (.492)

Championships won as owner: None

Bottom line: How bad did the Maloofs want to leave Sacramento? 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 taking a bath in the team’s sale in 2013 after their casino business hit the skids.

#12: George Shinn

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

Record as owner of teams: 964-883 (.521 winning percentage)

Championships won as owner: None

Bottom line: George Shinn, a religious zealot, saw his reputation come undone during a sexual assault trial in 1999. Acquitted of 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.

#11: 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)

Record as owner of team: 500-534 (.483 winning percentage)

Championships won as owner: 1918

Bottom line: 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.

#10: Jimmy Haslam

Teams owned: Cleveland Browns (2012-present), Columbus Crew FC (2019-present)

Record as owner of teams: 27-84-1 (.121 winning percentage)

Championships won as owner: None

Bottom line: 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.

Haslam’s company, Pilot Flying J, ripped the working man off by withholding $56 million in gas purchase rebates. He paid a $92 million fine to avoid federal prosecution.

#9: 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-present)

Record as owner of team: 1,346-1,406 (.492 winning percentage)

Championships won as owner: None

Bottom line: 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.

#8: Jed York

Teams owned: San Francisco 49ers (2008-present)

Record as owner of team: 82-93 (.468 winning percentage)

Championships won as owner: None

Bottom line: Jed York is the definition of being born on second and acting like you hit a double.

He forced out head coach Jim Harbaugh in favor of defensive line coach Jim Tomsula. The Niners are 17-47 since that move.

The San Jose Mercury News called York "clueless" after Harbaugh’s firing. That's kind compared to what some fans call him.

#7: George Reynolds

Teams owned: Darlington FC (1999-2004)

Record as owner of team: 74-69-87 (.321 winning percentage)

Championships won as owner: None

Bottom line: 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.

#6: Ted Stepien

Teams owned: Cleveland Cavaliers (1980-83)

Record as owner of teams: 66-180 (.268 winning percentage)

Championships won as owner: None

Bottom line: 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.

#5: Jerry Richardson

Teams owned: Carolina Panthers (1995-2018)

Record as owner of team: 183-193 (.486 winning percentage)

Championships won as owner: None

Bottom line: 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.

#4: John Spano

Teams owned: New York Islanders (1997)

Record as owner of teams: 29-41-12 (.353 winning percentage)

Championships won as owner: None

Bottom line: 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.

#3: Harold Ballard

Teams owned: Toronto Maple Leafs (1971-1990)

Record as owner of team: 549-713-207 (.373 winning percentage)

Championships won as owner: None

Bottom line: 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."

#2: Marge Schott

Teams owned: Cincinnati Reds (1984-1999)

Record as owner of team: 1,300-1,225 (.514 winning percentage)

Championships won as owner: 1990

Bottom line: 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)

Record as owner of teams: 987-1,645 (.375 winning percentage)

Championships won as owner: None

Bottom line: Donald Sterling was 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 Steve Ballmer for $2 billion.