10 Worst Owners In Sports History

October 30, 2015  —  By

10. David Glass, Kansas City Royals

David Glass
Ed Zurga/Getty

Don’t let recent success blind you to an ample history deserving of scorn. After running arguably the worst non-arms-manufacturing company in the world, Walmart, Glass became sole owner of the Royals in 2000 and immediately treated baseball the way Walmart treats people.

Amid a jackal pack of ownership that included a (future) commissioner guilty of collusion to fix player salaries, Glass – then the team’s president and CEO – stood out as an anti-labor hardliner during the 1994 strike, wanting to bring in scab players for a monstrously un-telegenic spectacle summarizing the kind of fuck-you tactics Glass learned at the Bentonville, Arkansas smile-time sociopathy juggernaut. He simultaneously advocated a hard salary cap in baseball, not to create an even playing field with large-market teams but to have a paper excuse to wave in doubters’ faces explaining why he didn’t spend anything on his team. Glass went ahead without one, with team payrolls routinely languishing in the bottom half of the league during his tenure, with notable years like 2000 (28th), 2003 (29th), 2005 (29th) and 2011 (30th). That’s out of 30. The last two years, Royals payroll has leapt to 19th in the league, but don’t let the 2014 World Series run fool you. Fans have every reason to expect them to regress, and every expectation that Glass won’t spend to correct that (Goodbye, Billy Butler.) After all, four seasons of 100 losses and an average of 92 losses per season under his tenure is a much bigger sample size.

Last, in 2006, Glass was all about that entrepreneurial spirit when renovations to Kauffman Stadium were furnished by a countywide sales tax, in exchange for discounts at certain games. Rolling back prices every day!

9. Mike Brown, Cincinnati Bengals

Mike Brown
Joe Robbins/Getty

Sometimes futility and incompetence are enough without the real world intruding too much. Consider Mike Brown, son of legendary coach Paul Brown, whose tenure has been so awful that all joy seems like accident.

Coming into this year, the Bengals were a combined 145-222-1 since 1991, a winning percentage of .394. Since that time, they’ve had four head coaches, the most successful of which, Marvin Lewis, has a .522 winning percentage and still doesn’t understand how timeouts, challenges or offenses work. They have had 15 starting quarterbacks, and Andy Dalton is considered a bright spot here, not just in terms of his albedo. Brown’s first move as Bengals owner was to fire the well-liked Sam Wyche, presumably for having taken the Bengals to the Divisional Round the year before. He immediately replaced him with Dave Shula, perhaps because when you owe your football job to your dad, game recognizes game. (And somewhere in America, Kyle Shanahan stubbed his finger against the TV tube and said, “One day that will be me.”) Brown employs himself as the head of talent operations, leaving the General Manager position empty and the Bengals’ front office a league-wide joke exceeded only by the Cowboys’ Jerry Jones.

Meanwhile, despite the sort of loyalty that saw Brown stand by Shula (19-52, .268) and a slew of felonious players, he used a flimsy excuse to declare his lease with Cincinnati broken and that he was considering moving the team to Baltimore. Cincinnati blinked and awarded him what The Wall Street Journal described as “one of the worst professional sports deals ever struck by a local government,” one that was “unusually lopsided and risky” and soared over budget. Debt has ballooned to over $1 billion on the project, which also includes the Reds’ Great American Ball Park, while other public space development has ground to a halt, child services and juvenile justice budgets have been slashed, sheriff’s department and school funding have been cut and property tax cuts bundled with the stadium project as a selling point have been rescinded. That’s a high price for sucking.

8. Jimmy Haslam, Cleveland Browns

Jimmy Haslam
Jason Miller/Getty

Let’s stay in Ohio with poor Jimmy Haslam, who grew up on the rough and tumble sheets of a bed paid for by the corporation his dad founded and of which he’s now CEO. (Both the bed and the company.)

Jimmy, a man so lonely that he has to travel all the way to Tennessee to see family (his brother is the governor) or Washington, D.C. to see a friend (his college roommate is a senator), recently got in trouble with the law, and he probably got by with a little help from them. In response to a systemic company policy to defraud customers on gas rebates, Jimmy’s Pilot Flying J truck stop corporation paid $92 million in penalties and over $56 million in restitution for customers. Jimmy evidently ruled the company with the iron-colander mind of a true leader, claiming he didn’t know what was going on. Thankfully, he avoided jail time!

Meanwhile, Flying J is the “the Number One [fuel] supplier to the drilling and fracking [industries],” and Jimmy and his governor brother (a Flying J shareholder) are behind a plan to frack the Cumberland National Forest. And in case you were wondering how he does with the team, Jimmy was the reason for both the rapid hiring of Rob Chudzinski after Chip Kelly passed on the Browns coaching job and the rapid firing of Chud after one season, a move that was almost universally panned. He then oversaw an embarrassing coaching search where candidate after candidate rejected the job in the media, further poisoning whatever appeal the perennially doomed position might have had. He then tried to mortgage the future by trading multiple picks for 49ers Head Coach Jim Harbaugh, then did a little of the same by trading up in the draft for Johnny Manziel, supposedly because a homeless man told him to. That’s usin’ your One Percent.

7. Dan Gilbert, Cleveland Cavaliers

Dan Gilbert
David Liam Kyle/Getty

We don’t even need to stray from Cleveland now (congrats, Ohio!) to talk about Dan Gilbert. When he hoists a Larry O’Brien Trophy sometime in the next few years, it’s going to be really easy for fans to forget that Gilbert is a massive dick, but hopefully haters will always be around to remind us. That’s what history is, haters with long memories. It even comes from the Greek word for haters.

Anyhow, despite having the best player in the world, Gilbert never evinced interest in supplying him with good teammates. (Zydrunas Ilgauskas! The decomposing body of Shaquille O’Neal, a.k.a. “The Big Corpse.”) Every offseason, the NBA narrative was, “Will Gilbert get LeBron any help?” And every year the answer was, “Nah.” When LeBron took a pay cut to join friends Dwyane Wade and Chris Bosh in Miami, Gilbert was robbed of the convenient “unlike me, this player is greedy!” narrative and instead wrote the most screwheaded Dear John rebuttal letter possible. In Comic Sans, the font reserved for form letters from moms. (Read it. The entire thing sounds like an insane missive you’d find on the ground amid a mass suicide of people in personalized track suits.) Gilbert argued that LeBron had “quit” on the Cavs, ignoring how James had played through an elbow injury during the playoffs and how he’d just offered that same quitter a $120 million contract. Now LeBron has bailed his ass out, through no fault of his own. The Heat are aging like the Nazi who drinks from the wrong grail, and the Cavs are young, will be able to pay him and play in a place near LeBron’s mom. That’s it.

Meanwhile, Gilbert, like all rich swine, paints himself as a moral and responsible businessman. That his team occupies a taxpayer-funded arena, and he grew rich peddling reverse mortgages and allegedly misleading loan offers makes him a perfect oligarch stereotype. It gets worse when you note that, in the spirit of free-market competition, he waged the most expensive electoral campaign in Ohio history to win a casino monopoly that drains the local economy. He verges on cartoonishly evil territory when you also realize that he is one of the largest private landowners in Detroit and last year was pushing for the city’s unelected Emergency Manager to default on $3.5 billion in unpaid, earned employee pensions.

6. Clayton Bennett and Aubrey McClendon, Oklahoma City Thunder

Clayton Bennett
Nathaniel S. Butler/Getty

There are few sports acts more despicable than buying a team, promising you really want to keep it where it is and trying to extort every last cent out of a city when you have every intention of moving at the first opportunity.

After purchasing the Seattle SuperSonics in 2006, Bennett and McClendon declared that Seattle’s arena was insufficient for the team’s future needs and demanded over $500 million in public funds for a new one. When Seattle balked, Bennett and Co. hunkered down for a protracted legal fight. Meanwhile, McClendon committed a classic gaffe, if you’re referring to the political definition of gaffe: when someone says what they really think. While he went on to aspire to “break[ing] even” on a future project in Seattle (i.e. socializing all construction costs, privatizing all profit), he stated, “We didn’t buy the team to keep it in Seattle.” And they didn’t. (NBA Commissioner David Stern fined McClendon for saying he was doing what everyone already knew he was doing.) Later e-mails divulged plans to move the team were hatched before it was even purchased.

There’s really nothing else you need to say about a group of rutting slop-pigs like this. But, in a pinch, you could add a couple things. One, Bennett and McClendon benefited from $120 million in corporate welfare from Oklahoma City to improve the arena and build a practice facility. Two, both Bennett and McClendon are heavy Republican donors, with McClendon making his fortune on fracking and screwing landowners out of royalties as they sit above the toxic sludge, then spending the proceeds on climate-change denialism and the Swift Boat Veterans for Truth campaign.

5.The DeVos Family, Orlando Magic

Richard Devos
Reinhold Matay/AP

Amway. That’s all anyone should have to put here. Richard DeVos co-founded Amway, cheery pyramid scheme for every climbing sub-Stepford serial neighborhood harasser in America and general font of endless grossness. But he’s since begun transferring control of his various empires to his children, and together they are a giddy clan of homophobes.

Huffington Post neatly summarized the extent to which DeVos and offspring have flung millions into groups that not only want to halt civil rights for gays but roll back existing ones. To give you an idea of some of these groups, DeVos’ foundation donated $235,000 to a group called The Alliance Defending Freedom, which “seeks to recover the robust Christendomic theology of the 3rd, 4th and 5th centuries.” Ah, yes, think of the robust liberty that flourished from 200-400 A.D.

At the same time, DeVos’ son and daughter-in-law both contribute tirelessly to turning public education into a vertically integrated commodified profit scheme, and his daughter-in-law’s brother is the founder of Blackwater.

Finally, despite being a billionaire throwing millions of dollars away per year to keep punishing gays for being gay, DeVos claimed that he couldn’t run a profitable sports team in the old Orlando Arena. So he dug deep in the playbook of movement conservatism and claimed that the city could make money by fulfilling an obligation to the public good by paying to make him profitable. Hence, the Amway Arena, the 12-percent privately funded $480 million facility floated by public bonds dependent on fleecing vacationing rubes. It took two years for an independent agency to rate those bonds junk. Maybe things would be different with more fans at games. Not just gay ones. Anyone.

Fun fact: Despite “struggling” to run a profitable franchise, DeVos’ advertising efforts outside of greater Orlando are practically nonexistent. Drive around greater Tampa Bay and ask any one of the nearly 3 million citizens currently living within two hours’ drive from the arena if they want to see a basketball game and watch them either look at you in total bafflement, explain that the USF Bulls sucked last year, or demur because they don’t have time to drive to Miami right now.

4.Jerry Jones, Dallas Cowboys

Jerry Jones
Rodger Mallison/Getty

Again, sometimes incompetence and/or looking and behaving like a hungover albino scrotum lurching into its eighth decade on Earth trumps social evil. Sure, Jerry made his money in oil, which is probably why just looking at the bloated monstrosity of a stadium he built can suck another 1,000 barrels out of the earth before you blink, but his brand of toxicity remains acting as the sybaritic embodiment of the Dunning-Kruger Effect.

Like Mike Brown, Jerry is both the owner and General Manager of his team, which is the football version of the attorney who represents himself: He has an idiot for a client. Jerry immediately fired the Cowboys’ only head coach, Hall of Famer Tom Landry, and GM Tex Schramm, the man who’d effectively run everything for the previous 29 years. Though their ouster was overdue, Jerry handled it about as smoothly as excommunicating a nun on her name day by punching her through a stained glass window. Luckily, the even more incompetent Minnesota Vikings handed him the worst trade in football history just months later, giving the Cowboys the building blocks of their dynasty. Not fucking up someone else’s unforced error probably marks the last smart thing Jerry’s done, with one playoff victory since 1996 to the team’s name.

Claiming “disloyalty,” he parted ways with two-time Super Bowl winning coach Jimmy Johnson, later stating that “any one of 500 coaches” could have won with the Cowboys. He handed the reins to Barry Switzer, the Admiral Stockdale of the NFL, and Barry rode the last gasp of Cowboys inertia to a third title. It’s all been downhill from there. Coaches Dave Campo, Chan Gailey, Wade Phillips. Quarterbacks Chad Hutchinson, Quincy Carter, retreads Drew Bledsoe and Vinny Testaverde. Jones even hired walking schtick Bill Parcells to chew gum and say “c’mon!” real loud, despite the growing sense that Parcells’ bullshit doesn’t work under a salary cap and without defensive coordinator Bill Belichick.

Jerry passed on drafting Randy Moss, gave two first-round picks for veteran Joey Galloway (the Seahawks used one on Shaun Alexander), and three picks for Roy Williams, who went on to catch 13 TDs in 40 games. And then there’s all the other hands-on stuff: from walking down to the field and seeming to supervise Tony Romo’s medical diagnosis when the man fractures his spine, to sexual harassment. All this before mentioning Arlington’s $325 million contribution (or everyone else’s) to building “Jerry World,” a stadium that on game day uses more energy than Liberia. Drill, Jerry, drill.

3. James Dolan, New York Knicks

James Dolan
James Devaney/Getty

A recent poll of over 200 ESPN panelists named James Dolan the worst owner in the NBA, and it’s not hard to see why. The Knicks posted losing seasons from 2001 to 2010, and they’ve won only one playoff series since 2000. Most of that can be put down to Dolan’s colossal mismanagement.

Where to begin? Maybe something like, a good indicator that you are a legendary fuckup is when an NBA rule is created and named after something you did. That’d be the Allan Houston Rule, based on the Knicks extending the seven-year veteran a further six years and $100 million, despite the next highest contract offer being only $75 million. Teams can now release one player without having that player’s salary weighed against the league luxury tax, although the salary still counts against the cap. Oddly, the Knicks bet that the injured, miserable Houston would retire, instead using the Houston Rule against the atrocious Jerome Williams contract they’d just traded for.

Or what about five years and $30 million for center Jerome James, based on an eye-catching postseason run that belied mediocre regular season numbers? James showed up the next year like he’d spent the offseason practicing Golden Tee at Golden Corral, then played 86 games for the Knicks in his first two seasons and four in his last two. Then there’s the Eddy Curry trade – which, I mean, Jesus Christ. Or not re-upping Donnie Walsh as GM after he started cutting out the Knicks’ deadwood contracts and adding parts still contributing to the recent winning seasons. Or firing Larry Brown with four years and $40 million left on his contract when everyone knows you only have to wait another year or so for Brown to get bored and quit. Or replacing Larry Brown with GM Isiah Thomas, who continued his GM duties just as badly. Or Dolan’s company and Thomas losing a lawsuit to Anucha Browne Sanders, who claimed that not only did Thomas sexually harass her but that Dolan fired her in retaliation.

And then there’s everything about Dolan outside the Knicks to loathe. Like his running the New York Rangers into the ground for a decade, despite high payroll. Or the fact that he came to his exalted position at Madison Square Garden by working for his dad’s company, Cablevision. Or the fact that on November 6th, the National Labor Relations Board charged Dolan with “illegally threatening to withhold employee pay unless the employees voted against joining a union.” Or finally, spare us, O Lord – being so wholly immunized from taste, accountability and objective-fucking-reality that he not only performs live with a band called “JD & the Straight Shot” but released a blues single called “Under That Hood” about Trayvon Martin. JD & the Straight Shot also booked themselves to open for the Eagles at Madison Square Garden.

2. Jeffrey Loria, Miami Marlins

Jeffrey H. Loria
David Santiago/Getty

If you live outside the tax base of Miami, the most despicable thing Jeffrey Loria ever did came on the heels of one of the smartest things a sporting municipality every did: say no.

After an initial investment of $12 million in the Montreal Expos, Loria triggered a series of showdowns with fellow team owners and local government until he wound up with 94 percent control, an alienated fanbase and a sweetheart ride out of town. Loria sold the Expos to “Expos Baseball, LP,” essentially Major League Baseball, for $120 million. He then bought the Marlins for $158.5 million, with the $38.5 million difference ponied up by MLB in an interest-free loan. After that, he committed to a strategy of cost-control with cheap young talent, selling off everything else, letting revenue sharing do the work of profit-making and crying poverty to the City of Miami, while resorting to the same threat game as in Montreal. (“San Antonio is a very viable market, and they’re very serious. Read my lips: They’re very serious.”) It worked. Loria erected a white-and-pastel mausoleum massively underserved by public transportation, one so empty that the retail spaces in and surrounding it as well as parking remain un- or under-leased, cratering any illusion of the “revenue” that a publicly financed stadium would bring. In exchange, through 2048, the City of Miami is on the hook for $2.4 billion. With a B.

To complete the illusion that Loria would now use his new stadium to field a competitive team, he bought a lot of free agents, signed them to backloaded deals, then shipped them out within the year in a stunning 12-player trade that reduced his payroll obligations by $160 million. He even lied and told Jose Reyes to buy a house in Miami four days before exporting his ass to Canada. (So many awful things happened that year that you might as well just click this.) Loria is going to eschew free agents, trade away good players for prospects at the height of their value and keep “rebuilding” and pocketing revenue-sharing checks until he dies. Here’s what baseball fans get in exchange: Go fuck yourself. In the meantime, he’ll also probably continue meddling in baseball operations, switching starting pitchers and holding up talent moves, like he does already.

And he’s already started on the competitiveness shell game again, signing slugger Giancarlo Stanton to a heavily backloaded $325 million contract that Keith Olbermann sublimely tore to bits just a day later. But you get to make those decisions when you’re someone who got a start in this world buying art for Sears. Who are we to judge a baseball man who has drunk so deep from the cup of life? After all, besides immiserating and plundering two baseball towns and every fan in them, Loria’s great contribution to the world is a book of philosophy based on Peanuts comic strips where he assures us that the pre-teen characters of that world aren’t into wife-swapping.

1.Daniel Snyder, Washington Redskins

Dan Snyder
Patrick Smith/Getty

If you’ve been paying attention to football this last year, you probably know Snyder as the staunch defender of an unambiguously racist name who can’t stop putting a loafer in his mouth every time he opens it.

Snyder has marshaled every resource of the rich white asshole invoking tradition to defend the indefensible. There’s this pro-Redskins AstroTurf campaign from a giant PR firm. There’s Snyder co-opting any local media going knives-out on the name or the fact that his team is stupendously mismanaged. There’s Snyder trying to buy silence from Indian tribes. There’s Snyder trotting out multiple Indian defenders of the name who aren’t even Indians, when he’s not sitting in his luxury box with a Navajo Nation leader recently kicked out of office under corruption allegations and in disgust at partnering with Snyder’s “Original Americans Foundation,” a disingenuous whitewash PR group. There’s Snyder sticking his fingers in his ears and pretending the Redskins were named to “honor” an “Indian” coach who turned out to be a German-American misrepresenting his race to avoid the WWI draft. Or sometimes he decides the name is meant to “honor” Indian “heritage” in general, and not as a marketing gimmick by their legendarily racist owner to identify the team with a much more popular baseball franchise.

And that’s just the name. You could go on for pages about the paranoid, Hitler-in-the-bunker mentality of the team, or the blithe unconcern with a shredded field and player health that already nearly Cuisinarted RG III’s knee. And you could go on for pages and pages and pages of what a clusterfuck of tire fires the Redskins have become under Snyder’s tenure, all set ablaze by the flaming sack of dogshit that is what passes for his conscience. In fact, someone already has. Dave McKenna of the Washington City Paper wrote a devastatingly hysterical A-to-Z guide to every contemptuous, miserly, greed-headed, soul-dead move Snyder has pulled in D.C., every bit of it true. Snyder sued McKenna and the paper anyway, because he wanted to see if the size of his war chest would back them down. Because he could. Because he’s Daniel Snyder, and because fuck you. Fuck your access to a true narrative, fuck your local pride, fuck your fandom, fuck your pocketbook, fuck your fun and fuck a genocide.

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