4. Jerry Jones, Dallas Cowboys
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.