As long as sports have been played in organized leagues, there have been team owners who have disgraced their respective games. Scoundrels, cheapskates and spoiled brats have always found a way to rip defeat from the jaws of victory — none worse than these 10 worst owners in sports history.
1. Harry Frazee, Boston Red Sox (1916-1923)
The infamous Harry Frazee is the man who sold Babe Ruth to the New York Yankees for $125,000 and started the 86-year “Curse of the Bambino.” Legend has it that Frazee used the ill-gotten gains to finance his Broadway play “No, No, Nanette.” After selling the “Sultan of the Swat” in 1919, the Red Sox did not have another winning season until 1935 and didn’t win another World Series title until 2004. Frazee bought one of baseball’s best teams — a club that won the World Series in 1912, 1915, 1916 and 1918 — then promptly sold its best player and ran the franchise into the ground.
2. Donald T. Sterling, Los Angeles Clippers (1981-present)
Notoriously racist slumlord Donald Sterling has an 874–1620 record (.350 winning percentage), with 28 non-winning seasons in his 31 years (prior to 2012-13) owning the Clippers. Despite just three winning campaigns (1992, 2006 and 2012), L.A.’s “other” NBA team has made the playoffs five times by default under Sterling. His many off-the-court indiscretions include paying the largest housing discrimination settlement involving apartment rentals in Justice Department history, being sued by Hall of Famer and longtime Clippers GM Elgin Baylor for age and racial discrimination, being sued for sexual harassment, and giving casual yet graphic testimony under oath regarding his preference for prostitutes.
3. Dan Snyder, Washington Redskins (1999-present)
Dave McKenna’s piece on Dan Snyder for the Washington City Paper is a comprehensive breakdown, albeit two years old, of the Redskins owner and his greedy, manipulative, petty ways. Snyder’s list of terrible free-agent signings includes washed up overpaid former All-Pros like Jeff George, Deion Sanders, Bruce Smith and Albert Hayneworth. He’s also not afraid to hire a has-been or never-was to run the show, with Norv Turner (1999-2000), Terry Robiskie (2000), Marty Schottenheimer (2001), Steve Spurrier (2002-03), Joe Gibbs (2004-07), Jim Zorn (2008-09) and Mike Shanahan (2010-present) all coaching during Snyder’s reign.
4. Marge Schott, Cincinnati Reds (1984-1999)
Chain-smoking, slur-spewing Marge Schott was banned from MLB from 1996 until 1998 for her outspoken hate-speech against pretty much all races and orientations — except for Adolf Hitler; Schott made it known that she was a big fan of Hitler and the Nazi Party. The Reds did win the 1990 World Series, in one of the two playoff appearances Cincy made under Schott.
5. Charles Comiskey, Chicago White Sox (1901-1931)
Another historic swindler, Charles Comiskey planted the dishonest seeds for arguably the worst sports scandal in history. The 1919 World Series “Black Sox Scandal” has its roots in Comiskey scamming ace pitcher Eddie Cicotte out of a $10,000 bonus he was set to receive for winning 30 games. With Cicotte — who earned a $6,000 salary that season — sitting at 29 wins, Comiskey ordered manager Kid Gleason to bench Cicotte for his final five starts in order to avoid paying the bonus. According to the book Eight Men Out by Eliot Asinof, Cicotte resisted taking mob money to throw the World Series until being denied a chance to earn his bonus by Comiskey.
6. James Dolan, New York Knicks (1999-present)
The son of Cablevision founder Charles Dolan, little Jimmy was a wannabe rock star with a few drug, alcohol and anger issues before inheriting his way to being one of the worst owners in sports history — mismanaging both the NBA’s New York Knicks and NHL’s New York Rangers as the top dog at Madison Square Garden. Dolan stood by the equally incompetent Isiah Thomas for most of the 2000s, despite an ugly sexual harassment lawsuit involving Thomas and an extensive history of bad free-agent signings, terrible trades and the squandering of numerous high draft picks — usually as part of one of the aforementioned terrible trades. In 2005-06, the Knicks had the NBA’s second-worst record despite having the Association’s highest payroll. But at least Dolan has provided plenty of material for comedy-sportswriters.
7. Every NBA Owner in Charlotte History
The NBA in North Carolina makes sense in theory. The Tobacco Road hoops traditions of UNC, Duke, NC State and Wake Forest are strong. But the transition from college to the pros has never worked in the state that was first in flight. All three owners in Charlotte’s NBA history — with the expansion Hornets and Bobcats — have failed.
George Shinn, Charlotte Hornets (1987-2002)
Shinn was a Court TV fixture during his 1999 kidnapping and sexual assault trial before ripping the Hornets out of Charlotte and relocating the team to New Orleans in 2002.
Robert Johnson, Charlotte Bobcats (2004-2010)
The founder of BET and first black billionaire, “Bob” named an NBA team after himself — as in “Bob-cats” — before selling the club to “His Airness” in 2010.
Michael Jordan, Charlotte Bobcats (2010-present)
As painful as it is for longtime MJ fans to admit, the greatest basketball player of all-time has been one of the sport’s worst owners, as last season’s 7–59 record and record-low 10.6 winning percentage proved.
8. CBS, New York Yankees (1964-1972)
The Columbia Broadcasting System had a big eyeball on the Bronx Bombers’ worst stretch in franchise history. After winning 20 World Series titles before CBS bought the pinstripes in 1964 — including championships as recently as 1961 and 1962 — the Yanks only made the playoffs once (1964) under the watchful eye. The immediate failure included finishing second in the division for the first time in 40 years in 1965 and a last-place finish in the AL for the first time since 1912 in 1966. Luckily, CBS canceled their own show and sold the club to the “Boss,” George Steinbrenner, whose extended legacy includes seven World Series titles.
9. William Clay Ford Sr., Detroit Lions (1963-present)
The last living grandchild of automotive pioneer Henry Ford is possibly the least innovative owner ever. Ford’s lowlights include the only 0–16 season in NFL history in 2008, keeping Matt Millen as the club’s primary decision-maker for eight years despite a 31–97 record (.242 winning percentage) and absolutely no signs of improvement, and the national injustice of wasting the sheer genius of Barry Sanders, who may or may not have retired in his prime due to the leadership behind the wheel in Detroit.
10. Jeffrey Loria, Miami Marlins (2002-present)
Loria sold the Montreal Expos to MLB’s other 29 teams before turning around to buy the then-Florida Marlins in 2002. The Marlins won the World Series in 2003, then sold off the team — just like the Fish did after winning the World Series in 1997. Fair enough. But Loria’s latest budget cuts are shameful and inexcusable. After spending over $500 million in public money from taxpayers and the city of Miami in order to build Marlins Park, the Marlins pulled the bait and switch — trading away nearly every player of note on the roster. Shortstop Jose Reyes, starting pitchers Josh Johnson and Mark Buehrle, catcher John Buck and utility speedster Emilio Bonifacio were shipped to the Toronto Blue Jays in a pennies-on-the-dollar salary-dump trade.