Most Infamous Owners in Sports History

When it comes to owning a sports franchise, there is no universal template for success, or even style. For both historically successful teams and those mired in mediocrity, there are examples of owners of every conceivable approach. 

Some owners have conducted business largely out of the spotlight, with quietly working with their leadership to assemble a winning team, while others leave no obvious footprint on a period of failure. Either way, the prevailing consensus seems to be that the best owner is a quiet owner—only speaking publicly when a serious situation arises. 

Then there are owners who make it their business to alert everyone and anyone as to their importance within the franchise—be it going down with the ship, guiding it into the port with a hero’s welcome, and everything in between. Often micromanagers lacking in everything but wealth, winning often comes second for these owners, who value doing it “my way,” as opposed to the “right way.” 

There’s a fine line between famous and infamous, which is quite often, although not always, defined by wins and losses. Fickle fans are willing to overlook almost anything if a franchise is winning, but they’re far less forgiving during prolonged stretches of futility. Combine losing with any other bad behavior and you’ve got the perfect recipe ownership infamy. 

These are some of the most infamous owners in sports history.  

Jimmy Haslam

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Team: Cleveland Browns 

Tenure: 2012-Present 

Considering he’s only owned the Browns for just over two years, the fact that Jimmy Haslam even made this list is a testament to his character and business acumen, or lack thereof. The relationship between owner and fans in Cleveland got off to a very rocky start when it was revealed upon his acquisition that Haslam is “1,000 percent” a Steelers fan and had been a minority owner in Pittsburgh since 2008. 

Although he sold his shares in 2013, Haslam hasn’t done much else to inspire confidence among Browns fans. The company Pilot Flying J, of which Haslam is CEO, has been the recent target of federal investigations by the FBI, IRS and U.S. Department of Justice. In 2014 Haslam and his brother Bill, the governor of Tennessee, “agreed to pay a $92 million penalty for cheating customers out of promised rebates and discounts.” 

Despite being outed as a very shady businessman, Haslam hasn’t shied away from the spotlight—in fact, he’s done just the opposite, having drafted Johnny Manziel in the first round on the advice of a homeless man in 2014. Not only has Haslam become one of the most outspoken owners in the NFL, he’s also got the itchiest trigger finger—the Browns are on their third coach and third general manager since being acquired by Haslam in 2012. 

Clayton Bennett & Aubrey McClendon

Sue Ogrocki/Associated Press

Team: Seattle SuperSonics/Oklahoma City Thunder

Tenure: 2006-Present 

In 2006 Aubrey McClendon and Clayton Bennett bought the SuperSonics from Starbucks founder Howard Schultz for $350 million. At the time of the deal they stressed that it was not their intention to move the team, provided they were able successfully come to terms with local and state officials on funds for a new arena. That was their official story anyway. 

According to Forbes, McClendon and Bennett “seemed to be sincere,” having negotiated in earnest with the town of Renton before the Washington legislature shut it down, refusing to allocate taxpayer money to the project. It worked out perfectly for the team’s new owners, who it was later revealed never had any intention of keeping the Sonics in Seattle—in 2007 that’s exactly what McClendon said in an interview with the Oklahoma Journal-Record. 

Incensed at McClendon’s deceptive actions and public comments, (then) NBA commissioner David Stern fined him a (then) record $250,000. Also fuming about the deception, Schultz filed suit against the new ownership group, hoping to get the sale voided. Months later he dropped the suit, conceding deception alone wasn't legal grounds to nullify the sale.T

That being said, things have worked out well in Oklahoma City, which makes McClendon and Bennett even more infamous to Seattle sports fans. 

Phillip Wrigley

Associated Press

Team: Chicago Cubs 

Tenure: 1932-1977

Heir to the chewing gum empire, Philip Wrigley inherited a vast fortune, which included the Cubs, when his father died in 1932. Two years later team president Bill Veeck, Sr. departed, at which point Wrigley took over club operations in Chicago, ushering in an era of abject futility that spanned more than four decades. Emphasizing business over baseball, Wrigley’s dedication to the bottom line shaped every decision he made—some with worse consequences than others.

In 1960 Wrigley established the “college of coaches,” essentially a bullpen of guys who would coach by committee, eliminating he need for a manager, a position he believed was “expendable.” The experiment was a chaotic disaster on which the plug was pulled in 1965. The Cubs were also among the last teams in MLB to establish a minor league system to develop players, with Wrigley opting instead to sign pro ready players and avoid the expense associated with owning minor league clubs. Eventually the number of available players dwindled enough to force his hand. 

In fairness to Wrigley, his tenure wasn’t all bad. He was meticulous with regard to the care and upkeep of Wrigley Field, always trying to improve the fan experience—probably to make up for how wretched the team was. When other owners were resisting broadcasting, fearful that it could negatively impact attendance, in 1948 Wrigley struck a deal with WGN-TV in Chicago to broadcast the home games of both the Cubs and White Sox. It happened just eight months after the first ever televised World Series. 

Perhaps Wrigley’s most noteworthy contribution to baseball was the All-American Girls Baseball Professional League, which he conceived of and financed. The AAGBPL filled the void when WWII forced the shutdown of MLB in 1943 and continued to operate until 1954. 

Art Modell

RON HEFLIN/Associated Press

Team: Cleveland Browns/Baltimore Ravens 

Tenure: 1961-2004

In November 1995 the late Art Modell made a decision that would come to define his entire legacy, if not his entire life. Supposedly feeling jilted by the city of Cleveland, which at the time had recently committed to building new venues for both the Cavaliers and the Indians, Modell stopped all negotiations with the city and held a late-season press conference at Camden Yards in Baltimore to announce his intention to relocate the team ahead of the 1996 season.  

In that moment he instantly became one of the most beloved sports figures in one city's history and the most reviled of another. The decision reportedly haunted him, but Modell always maintained his hand was forced, an assertion that was directly refuted by the Cleveland Plain Dealer in 2012. Obviously that didn’t do much to dissuade anger among still simmering Browns fans—not that they would've expected anything better. 

When Modell died in 2012 at the age of 87, the man celebrated in Baltimore bore no resemblance to the man skewered in Cleveland. Proving that time doesn’t heal all wounds, in 2014 an Ohio man was charged after a video he posted of himself urinating on Modell’s grave when viral. 

Jim & Robert Irsay

Michael Conroy/Associated Press

Team: Baltimore Colts/Indianapolis Colts 

Tenure: 1972-Present 

What Art Modell is to the city of Cleveland, Robert Irsay, and to a lesser extent his son Jim, are to the city of Baltimore. The name Irsay has been denounced in Baltimore since March 1984, when Robert Irsay moved the Colts out of town, quite literally, in the middle of the night. Lured to Indianapolis with the promise of a decade's worth of guaranteed attendance and a domed stadium, Irsay thought nothing of leaving in a lurch the fans that had supported the team for 31 years. 

Following his death in 1997, the Baltimore Sun described Irsay as “a meddlesome, impetuous team owner given to drunken fits of rage,” noting that in the city he would be “remembered best for drunken public appearances and unstable management … that drove away fans from a franchise that had been among the post popular in sports.” Though the family name has been somewhat rehabilitated in Indianapolis, Jim Irsay has earned a colorful reputation of his own. 

With the wardrobe of a mob boss and a big mouth to match, the younger Irsay has developed a love of the spotlight that rivals that of Cowboys owner Jerry Jones. Overactive on Twitter with a penchant for on camera rambling, it was only after he was arrested for DUI last March that Irsay finally took a step back. Initially it was self-imposed, but in September the NFL made it mandatory, slapping Irsay with a six-game ban and a $500,000 fine following his pleading guilty to misdemeanor charges stemming from his arrest. 

Fred Wilpon

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Team: New York Mets

Tenure: 1980-Present 

It’s hard to believe Mets owner Fred Wilpon is worth upwards of $500 million, considering he’s bad at business and even worse with money. In 2011 it was revealed that the Wilpon family had been in bed with infamous financier Bernie Madoff for over a decade. So reliant on the annual dividends from the notorious ponzi scheme were the Wilpons, as court documents show, that in 2002 they were the only thing keeping the Mets in the black annually. 

In 2013 Wilpon proudly declared the franchise’s money problems “over,” having settled a lawsuit by Madoff’s victims for $86 million, just a smidgen less than the billion they were seeking. But so far nothing has really changed for the reliably abysmal Mets, who have made the playoffs just once since 2001 and have a payroll that puts them in the bottom third of MLB for 2015. 

Wilpon’s poor people skills aren’t doing him any favors either. In 2011 he publicly insulted Jose Reyes and Carlos Beltran, calling them both overpaid in an interview with the New Yorker. He also said that All-Star third baseman David Wright, their franchise who's been with the team since 2004, is a nice guy, but not a superstar. Wilpon was probably just smarting at the time because that July marked the first of 25 $1.2 million checks that will be issued to Bobby Bonilla annually, the result of a deal he negotiated in 1999 which ultimately turned a $5.9 million buyout in a $29.8 million buyout. 

The Wilpons reputation took yet another hit in September 2014, when a lawsuit filed by a former employee alleges she was terminated for having a baby out of wedlock. The picture painted of the Mets in the complaint is, as one would imagine, less than flattering. 

James Dolan

The Star-Ledger-USA TODAY Sports

Team: New York Knicks/New York Rangers 

Tenure: 1999-Present 

An owner may sit atop the chain of command, but that doesn't mean the role comes without enormous pressure—the pressure to build a winning franchise while simultaneously running a profitable business is not unlike walking a high wire and it’s something very few franchises do well. However, achieving this harmonization between two oft-contradictory goals in New York City is a different beast; attempting to do it with two teams just masochistic. 

As Executive Chairman of the Madison Square Garden Company, James Dolan has been running operations for the Knicks and the Rangers since 1999. He is also CEO of Cablevision, a post he inherited from his father Charles, a cable visionary whose vision was behind game-changers like HBO and video-on-demand, in 1995. And just to irritate fans a little more, he also plays guitar in his very own blues band.

The problem with Dolan is that, like most middling offspring of legendary billionaires, he’s got the name but not the know-how. He certainly operates at a dynamo pace and engages in dynamo-style micro-management, but he is a rudderless dynamo. Dolan's level of personal engagement in the day-to-day affairs of the Knicks and Rangers is inversely proportional to their success—for the most part. A classic generational downgrade, overly confident and underly appreciative, Dolan waged war on his elderly father in 2005, seeking to further marginalize him. 

Dolan is a hands-on owner, in this case meaning everything he gets his hands on fails. Like when his strangely passionate campaign to stop a small group of Cablevision technicians in Brooklyn from unionizing resulted in him being busted for breaking federal labor laws. Under Dolan the Knicks have wasted untold millions on bad contracts and have been the poster-child for a once-proud franchise rendered dysfunctional in the era of NBA parity. The Rangers have fared somewhat better, contending in the Eastern Conference despite incidents like former John Tortorella declaring, "We just have to go about our business. I had my owner up here talking about a Stanley Cup, and that's a bunch of bull----." 

Mike Brown

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Team: Cincinnati Bengals 

Tenure: 1991-Present 

Speaking of classic generational downgrades, Bengals owner Mike Brown took over the franchise after his father, Paul Brown, died in 1991. With Brown acting as both owner and general manager, it’s probably no coincidence that Cincinnati hasn’t won a single playoff game since—their last postseason victory was in 1990. 

When it comes to Brown, there’s lots to loathe. First of all, he’s a well known cheapskate who, according to former Bengal Johnathan Joseph in 2012, puts strict rations on basic necessities for players like Gatorade and toiletries, making road trips particularly challenging. That’s probably why he won’t hire a qualified GM, the useless boob he has now is a lot cheaper. He’s also proven himself vindictive—just ask Carson Palmer about that charge. 

Speaking of vindictive, in 1996 Brown threatened to move the team (maybe even to Cleveland!) if Hamilton County wouldn’t pony up an estimated $250 million for a new stadium. The final cost to the struggling taxpayers is now estimated to be more than double that, with Cincinnati receiving more public funding than any NFL stadium ever. Nothing like the threat of relocation to burn bridges between owner and fans. 

In 2010 16 percent of the county’s annual budget was being put toward the debt. All that for a stadium that is usually half empty, unless the Steelers are in town. 

Glazer Family

JON SUPER/Associated Press

Team: Tampa Bay Buccaneers/Manchester United 

Tenure: 1995-Present, 2005-Present 

With the possible exception of Tampa Bay metro area, in the U.S. the Glazer family’s ownership of the Buccaneers isn’t a widely recognized or discussed as a major bone of contention. Probably because they haven’t been relevant for the last 11 years and have taken sucking to impressive new heights since 2011. The same cannot be said about the Glazer’s ownership of the English football club Manchester United, which has been the infected festering boil on the collective butt of one very passionate fan base since the late Malcolm Glazer acquired the team in 2005. 

Things got off to a very bad start between owner and fans, with one of Glazer’s first acts being to saddle the club with nearly $800 million in debt, which has reportedly cost the team upwards of $1.5 billion in finance charges since. The move sparked a flurry of protests in the UK which have continued in earnest to this day. Real outrage was kept at bay early on because Man Utd was still winning—they were Premier League champions three straight seasons from 2007-09. But having lost to hated rival Manchester City two of the last three seasons hasn’t done much to dull fan fury. Neither has the lasting bitterness over the sale of Cristiano Ronaldo to Real Madrid in 2009. 

The Glazer family’s role as a financially gluttonous and maniacal American super villain is continually driven home by the sports media, not just in England, but around the world. Articles such as “Why the Glazers’ ownership of Manchester United is to blame for their transformation into mere mortals,” published by the Mirror in January 2014, and “Manchester United Is Losing, but Glazers Aren’t,” published by the Wall Street Journal last August, often stoke the fire of an already seething fan base. 

That level of anger easily explains, though it doesn’t excuse, the less than remorseful reaction of certain Man Utd fans on Twitter following the death of Malcolm Glazer last May. Five months later it was revealed via a 120-page report that the FBI had been investigating threats made against Glazer dating back to his acquisition of the team, proving the public’s hostilities extend well beyond cold comments on social media. 

Jeffery Loria

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Team: Montreal Expos/Miami Marlins 

Tenure: 1999-Present 

In a world with many contenders, Marlins owner Jeffery Loria has as good a claim as anyone else in the running as the most hated owner in sports. An art dealer by trade, Loria’s involvement in MLB began in 1999, when he purchased a 24 percent minority stake in the Expos for just $12 million. He had been attempting to buy his way into baseball for 16 years, having failed five times before finally being approved by the league. 

Loria spent the next two years running the team into the ground and pushing out other owners. By 2002 he had gained 94 percent control of the Expos, which he promptly sold to MLB for $120 million. Commissioner Bud Selig fast-tracked the $158 million sale of the Marlins to Loria, sweetening the deal with a $38 million no interest loan to make up the difference. One year later the Marlins won the World Series, after which Loria moved promptly to dismantle the team. 

Between 2004 and 2009, Marlins teams ranged anywhere from below average to comically terrible—they bottomed out in 2006, finishing 19 games back in the NL East and a payroll under $15 million, which was $20 million less than the next lowest spenders. All those years of crying poor and lying through his teeth paid off for Loria, when Miami-Dade County finally cried uncle and approved funding for a new stadium in 2009. Marlin’s Park opened in April 2012 boasting a team stacked with costly free agents with backloaded contracts. In November Loria orchestrated a 12-player trade with the Blue Jays, a fire sale that saved the team $146.5 million. 

The Marlins have averaged 92 losses over the last three seasons, the futility of which has been reflected in their attendance. And as for that stadium the county financed with a $409 million loan? By the time it’s paid back in 2045, it will have cost taxpayers upwards of $2 billion. Loria has since been outed as a shady conman, not that it matters now.

Daniel Snyder

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Team: Washington Redskins

Tenure: 1999-Present

"Hail to the Redskins"—four words that are virtually obsolete and completely disconnected from the reality that is the Washington Redskins of the 21st Century. More than a few NFL franchises have seen the success of past decades transform into persistent failure, it's the cyclical nature of a parity-driven league, but Washington's fall has been particularly precipitous and devastating bereft of hope.

Though the once-storied franchise (three Super Bowl wins and five appearances in the modern era) troubles have no clear solution, it's no mystery that the dysfunction, mismanagement and instability of the team correlates with the decision-making of one Daniel Snyder.

The billionaire business "mogul's" most successful feat as owner has been finding new and inventive ways to tick off anyone and everyone; especially Washington's steadfastly loyal, tortured fan base and the local sports media. And he's been equally effective at achieving this as a citizen and businessman as well as Washington's owner.

Snyder has raised prices on things that fans struggled to comprehend as chargeable in the first place. He cut down protected trees. He created a team news network to employ local sports reporters as a firewall for criticism. He sued a local paper for publishing well established, but unflattering, facts about his tenure as owner. Oh, and there's that little matter regarding the team's name and it's meaning to Native Americans. The list is far too long for one slide, or even slideshow.

But, as owner, Snyder's legacy thus far is ultimately judged by the team's performance on and off the field. He's churned through eight NFL head coaches, fired a proven GM in favor of the inexplicable Vinny Cerrato, paid an absurd amount of money to a surly fat man who earned most of it somewhere other than on the football field, turned an electrifying Heisman-winning, nice guy quarterback and reason for hope into a key part of a power triangulation between Snyder, former coach Mike Shanahan, and now, Jay Gruden. And though the problems are many and the space limited, the bottom line is the team is 105-140 with four playoff appearances and two postseason wins.

Marge Schott

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Team: Cincinnati Reds

Tenure: 1984-1999

It’s hard to believe, but the late Marge Schott was once a very popular figure in the sports world. A chain-smoking alcoholic with a big mouth and a bigger ego—her St. Bernard was named Schottzie—Schott made a habit of saying and doing terrible things. In 1992 she was unsuccessfully sued by several Reds players who alleged she used the n-word and had “a policy of refusing to hire African-Americans.” 

The following year Schott was suspended for the season by MLB and again in 1996. Throughout that period she continued to use ugly slurs in reference to, among others, blacks, Jews, and homosexuals. Schott, it seemed, hated everyone but Adolph Hitler, whose only flaw, she argued, was going too far. She was eventually forced out in 1999, but an article in The Cincinnati Enquirer in 2004 still sung Schott’s praises, calling her “a woman of the people.”

Former Reds pitcher David Wells was left with a much different impression. In November 2014 he referred to Schott as a “psycho” and a cheapskate who made players pay for their own equipment, fly commercial, and handed out meal allowances that included pennies, nickels and dimes. Wells added, “I hated her. She was terrible. She was a bad person.”

Al Davis

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Team: Oakland Raiders

Tenure: 1966-2010

People who are iconic, but polarizing typically leave behind a steady legacy—regardless of whether they were loved or hated, the general sentiment stayed about the same over the course of their life. The late Al Davis was a unique case. Exuding that signature Brooklyn brash attitude that some people simply can't handle, he was eccentric, but no one doubts his place as one of the architects and true innovators of the modern NFL.

What makes Davis standout is how the man who was the Oakland Raiders, who transformed the franchise into one of the most successful—and feared—teams in the league, essentially drove them into the ground before he passed away in 2010. From 1967 until 1990, the Raiders were one of the most dominant AFC teams—winning three Super Bowls (and losing one), reaching the playoffs 16 times, and giving us historic moments like The Immaculate Reception. Davis innovated the passing offense, wasn't afraid to extend career opportunities to minorities, and helped create the Jack Tatums and Ken Stablers of the football universe.

He also filed costly lawsuits, picked fights with the NFL commissioner, and ruthlessly ditched/traded stars who fell out of favor. But, he was Al Davis; it came with territory, which was fine because the Silver and Black was the badass the NFL hated, but needed.

Then, with the exception of the blowout loss against Tampa Bay in Super Bowl XXXVII and a smattering of playoff appearances, the bottom dropped out of the franchise. Davis never ceded his hand in personnel and team operations, players like Bo Jackson and Charles Woodson gave way to busts and extreme-reaches like Robert Gallery, Darrius Heyward-Bey and...*gulp*...JaMarcus Russell. In the end, his legacy as a pioneer wasn't overshadowed by moments like the Lane Kiffin fiasco, or the fact the Raiders posted just six winning seasons from 1991 to 2010, but they became an important part of the story.

Harry Frazee

Associated Press

Team: Boston Red Sox 

Tenure: 1916-1923

When Harry Frazee, a theater owner from New York City, acquired the Red Sox in 1916, the team had won three World Series championships in the previous five seasons, in addition to their first in 1903. Boston’s roster was stacked with superstar players at the time, most famous among them being, of course, Babe Ruth. 

Under Frazee the Red Sox won the World Series again in 1918, but at that time things were already going downhill for him financially. It wasn’t long before he started selling off the team’s best players, including the fire sale that sent Babe Ruth and a number of other players to the Yankees, for which he was paid $470,000. 

The longstanding legend that Frazee sold Ruth specifically to finance the broadway show No, No Nanette makes for a fun story, that, however, is just a myth. Years later he was involved with the production of the show, but the timeline in between both events show no possibility of overlap. 

The reality is that Frazee overextended himself in purchasing the team and was drowning in debt. By 1923 the Red Sox were a hollow shell of what they had been just years earlier. With no players left to sell, Frazee sold the team to Bob Quinn for $1.15 million. 

Jerry Jones

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Team: Dallas Cowboys 

Tenure: 1989-Present 

What’s interesting about Jerry Jones is that he’s just as likely to end up on a list of the best owners in sports as a list of the worst. For all his faults, there’s no denying Jones’ success as a businessman. He bought the Cowboys for $140 million in 1989 and today the franchise is worth $2.3 billion, $500 million more than the Patriots, which is the second most valuable franchise in the NFL. 

There’s also no denying Jones’ passion for the game, which is only superseded by two things: his passion for the spotlight and his own ego. Jones doesn’t play well with others, having run through eight head coaches since acquiring the team in 1989. His relationship with former head coach Jimmy Johnson, who won two Super Bowls in Dallas, was particularly acrimonious. In 1994 Jones fired Johnson, later stating that “any of 500 coaches” could’ve won with that team. 

The success Jones has enjoyed as an owner has been largely overshadowed in recent years by the failure he’s experienced as the team’s general manager. Since 1997 the Cowboys have averaged 8.2 wins per season, having won just two playoff games over that stretch. With few exceptions, Jones has proven terrible at drafting—he was planning to draft Johnny Manziel in 2014, but was physically stopped by his son Stephen. Last September Jones said he was still “damn mad” about missing out on Manziel. 

Despite two decades of anecdotal evidence to the contrary, Jones believes he’s a top notch general manager and insists he’s done some of his best work in recent years. Not only does he have absolutely no plans to step down, the 72-year-old Jones expects to keep running the show in Dallas for the next 15-20 years. 

Donald Sterling

USA TODAY Sports

Team: Los Angeles Clippers  

Tenure: 1981-2014

Former Clippers owner Donald Sterling's transgressions are well known, indefensible, and the reason why he is now the former owner after a nearly 23-year tenure. The billionaire real-estate developer bought the then-San Diego Clippers in 1981 for $13 million and fielded a squad so mired in mediocrity (three playoff appearances and three .500 or better seasons before 2011-2012 is testing the boundaries of mediocrity) that stories about alleged racist comments and generally loathsome behavior toward players and coaches never seemed to gain significant national traction.

But, the stories persisted and Sterling's personal life and practices involving both the franchise and his real-estate business dealings offered plenty of corroborating evidence and rendered any benefit of the doubt, toothless. His troubles read like a power-ranking of wretched personal qualities: sued for sexual harassment in 1996, multiple lawsuits over unfair or discriminatory housing practices; including a Federal lawsuit filed in 2003. The allegations it contained underscored an obvious pattern—Sterling's words and actions toward minorities were racially biased at best, outright racist at worst.

Then 2009 NBA Draft pick Blake Griffin became one of the most exciting players to watch in the league, then the Clippers traded for point guard Chris Paul; all of the sudden the team had young, bonafide stars and were pretty good. The spotlight was on a thrilling, up-and-coming Clippers team and predictably, the glare proved disastrous for Sterling. Conversations recorded and then released in 2014 by his then "business associate" V. Stiviano showed the world Sterling's vindictive, racist attitude in disparaging statements about legendary Laker Magic Johnson.

Subsequent outrage and Sterling's absolute lack of contrition, or even self-aware response, expedited a lifetime ban and forced sale of the franchise by his estranged wife, Shelly, to former Microsoft COO Steve Balmer. 

George Steinbrenner

Ray Stubblebine/Associated Press

Team: New York Yankees

Tenure: 1973-2010 

The late George Steinbrenner ruled the Yankees with an iron fist for 37 years before succumbing to a heart attack in 2010 at the age of 80. Today he remains one of the most polarizing figures in American sports history. Steinbrenner wasn’t the type of person people have lukewarm feelings about. The mere mention of his name tends to elicit a very visceral reaction—people either love him or hate him. There’s very little middle ground. 

Early on it seemed no one hated Steinbrenner more than the people on his payroll. He changed managers 20 times in his first 23 seasons, among them was Billy Martin, who was hired and fired five different times. A notorious micromanager, Steinbrenner often butted heads with players, many of whom didn’t appreciate his overbearing policies regarding inconsequential things like hair length, something he was weirdly obsessed with. So over-involved was Steinbrenner that he was even known to occasionally direct traffic outside Yankee Stadium following games. 

For a guy with so many rules that demanded compliance from others, Steinbrenner proved more than willing to break the rules, and the law, on more than one occasion. In 1974 he was indicted on and later convicted of 14 counts stemming from illegal contributions to Richard Nixon’s re-election campaign, which resulted in a 15-month suspension from MLB. He was later pardoned by Ronald Reagan. In 1990 it was revealed that Steinbrenner had paid a shady gambler $40,000 to dig up dirt on Dave Winfield, who he’d signed to a 10-year deal worth $23 million in 1980 and wasn't performing up to expectation. Steinbrenner was suspended again and didn’t regain control of operations until 1993. 

All that aside, there is simply no denying Steinbrenner’s success. In 1973 he bought the struggling Yankees franchise, nine years removed from their last World Series win, from CBS for $10 million—today they’re worth over $3 billion. Under Steinbrenner the Yankees won more games than any other team, with a total of seven World Series titles and 11 AL pennants. His big spending ways forever altered the way business is done in baseball—Steinbrenner lamented the luxury tax enacted by the league in 2002, which may never have existed if it wasn’t for him.