How I Chose “America’s Biggest Assholes” and the Runner-Ups

By | May 25, 2017

Choosing “America’s Biggest Assholes” is a daunting task. First, America is not as old as most other countries and there’s not–despite what you may have read about this or that President over the years–really “an American Hitler” or “an American Genghis Khan.” American ruthlessness is usually a more subtle and corporate-infused variety so that it’s sometimes difficult to even tell who really started something or if 100 people are responsible.

Over the next week, I’ll be unveiling the “10 Biggest Assholes in American History” but I thought it might be helpful to know how I decided on these rankings—this is no mere slapped-together clickbait, but a seriously considered list—and also look at the Runner-Ups that were considered heavily, along with a reason they didn’t make the final cut.


1. I tried to focus on the dead. It’s true that there is an “alive” person in the runner-up section (as much as living in prison is alive), but mostly I limited my search to the dead because we can fully see the impact of their life’s work. That’s why you may be surprised to not find Dick Cheney, George W. Bush, or Donald Trump himself on this list.

2. Were they actually an American? Not every “American Asshole” is an actual American, which is why I had to sadly exclude such contenders as Italian-immigrant Charles Ponzi (namesake of The Ponzi Scheme) or Italian anarchist Luigi Galleani (who was like a Rockefeller wet dream turning people against unions with bombings) or Irish-immigrant Mary Mallon “Typhoid Mary” (who knowingly spread Typhoid to people) being the list’s sole woman, although there are some exceptions to the “Americans” rule in the Runner-up list.

3. It’s all about scale. Sure, Timothy McVeigh is technically a bigger asshole than just about anybody on this list, but I wasn’t going for isolated atrocities so much as people who created entire systems of death or oppression.

4. Were they real people? I was fully prepared to include such American monsters as Jim Crow or Willie Lynch (boogieman of Black Studies classes) before discovering neither of them were real people. Lynch, supposed inventor of a color-caste system that kept lighter skinned “house slaves” and darker-skinned “field slaves” from liking each other, may have never existed, and the term “lynching” didn’t come from him either. As for Jim Crow, the South’s segregation laws were actually named after a fictional blackface routine “Jump Jim Crow” performed by white actor Thomas D. Rice.

5. Who’s really responsible? You may notice the list has many contemporary choices on there and that’s partly because it’s a lot easier to find information on events after 1900. Early American history in particular is murky, and as deplorable as certain events are—like the Salem Witch Trials or the KKK—it can be difficult to pin it on one individual. Likewise, I don’t truly believe Lee Harvey Oswald assassinated Kennedy or did it alone, and even though John Wilkes Booth did assassinate Lincoln, there’s considerable reason to believe he was a pawn in a larger plot organized by carpetbaggers looking to make a fortune during reconstruction. In general, I tried to get at the truth as best as historical records allow, and it may be interesting to Trump (who said Andrew Jackson didn’t like the Civil War despite being dead before it started) that Andrew Jackson actually did favor the use of federal force to stop South Carolina from seceding back when they first threatened it during his Presidency decades before the actual Civil War.

Runners-Up to “America’s Greatest Asshole!” Hey, being the 20th to 11th biggest asshole in American history is no small feat…

20. Aaron BurrWho Was He? A former Vice-President of the United States, most known for killing Alexander Hamilton in a duel…Why Him? I actually don’t care at all that he killed the overrated Hamilton (thanks for the electorale college Hammy) in a duel that Hamilton tried to rig against Burr, you reap what you sow. What I do care about is Burr’s plot to try to swindle America out of the Louisiana territory and set up an England-dependent colony right next door, narrowly avoiding the charge of treason in an infamous trial…Why Didn’t He Make the Final Cut? Burr is a somewhat mysterious figure to me, and it’s quite possible he’s just “The Most Misunderstood Man in American History” rather than a huge, treasonous asshole. There’s also something mildly pathetic about his constant schemes for greatness that adds a pathos to him I find lacking in other historical assholes.

19. Charles MansonWho Was He? I doubt there’s many that haven’t heard of him, but he’s been serving life in prison for decades after manipulating several young women he was pimping out at the time into killing people for him, including Roman Polanski’s first wife Sharon Tate…Why Him? To me, he is the figure most responsible for killing the “flower-child” idealism of the hippie generation, and allowing Puritanical scolds to say “See, the kids really are out of control.” You can feel his “scared of the kids” presence in everything from the Columbine shootings to paranoia over Satanism that convicted “The Westboro Three” of wearing black while in the same town as child killings…Why Didn’t He Make the Final Cut? It simply became a matter of scale, and while I would like to blame him single-handedly for the deflowering of youthful idealism, I’m sure drugs, Vietnam, and gangs had something to do with it too.

18. William Henry Gist/Francis Wilson PickensWho Were They? South Carolina Governors who either got the ball rolling to secede by signing the order to do it (Gist) or were leading S.C. into the Civil War (Pickens)…Why Them? South Carolina had been itching to secede for decades, even going back to a beef with Andrew Jackson. Still, as the two men who finally made it happen and effectively began The Civil War, they led us (the South) into a hopeless battle, and a century of poverty and misery. It took a while before I could reconcile ranking them so low on this list…Why Didn’t They Make the Final Cut? Ultimately, no two people are to blame for the Civil War, and just being in charge of the state that seceded first isn’t reason enough. Especially when I think there are others (like Pickens cousin John C. Calhoun) who deserve much more direct blame. Speaking of…

17. “The Great Triumvirate” in the Senate including Senator John C. Calhoun, Henry Clay, and Daniel Webster…Who Were They? Three leaders in the senate often called “the greatest senators of all time,” but what was so great about these three assholes? Why Them? Daniel Webster was a first-class prick who reveled in being an elitist. If you’re looking for a case of an out-of-touch politician mocking his own constituents, you can’t do better than him. Henry Clay he may be the least odious of this trio, but he still conspired to steal the Presidency from Andrew Jackson so he could become Secretary of State under John Quincy Adams in “the Corrupt Bargain,” one of the biggest early backroom deals in American political history, and the first time the popular vote didn’t matter for President. And last but not least, John C. Calhoun who was so against trampling on slavery or the South’s right to own slaves, that he actually resigned the Vice Presidency under Andrew Jackson when it became clear Jackson wouldn’t allow South Carolina to secede. He’s often credited as the ideological Godfather of the secessionist movement…Why Didn’t They Make the Final Cut? The more I think about it, the more they might should have, being early predecessors to the type of behavior we hate in modern-day politicians.

16. Dr. H. H. HolmesWho Was He? Often credited as “America’s First Serial Killer” reports vary wildly on whether he killed 20 people or 200, and he became something of a mythical figure in American folklore, like a nightmarish Johnny Appleseed or an American Jack the Ripper…Why Him? He built a “murder hotel” worthy of the “Saw” films to gas, torture, and dispose of victims. It was located next to the Chicago World’s Fair of 1893 where he hoped to ensnare more victims. When you see a far-fetched serial killer film, just remember that even the killer from “Seven” wasn’t this elaborate or motivated…Why Didn’t He Make the Final Cut? Only nine of his victims could be confirmed and the scariest thing in his story is the elaborate nature of his “murder hotel.” In truth, it was hard to scale his crimes into a larger atrocious trend. Unlike…

15. James Albert BonsackWho Was He? Inventor of the first mass-cigarette making machine. Why Him? Before him, cigarettes were rolled by hand, but his machine could make 200 in a minute. This kicked off a global epidemic of lung cancer…Why Didn’t He Make the Final Cut? There’s no indication at all that anyone at that time knew cigarettes caused lung cancer, so unlike 1960’s Big Tobacco Executives, Bonsack actually can hide behind the “Ignorance is bliss” defense.

14. John D. RockefellerWho Was He? The richest American who ever lived, and quite possibly the wealthiest person who ever lived. At one time, he was the head of an oil monopoly that controlled 90% of American oil production…Why Him? There was just simply no way I could compile a list like this and not include the head of the biggest monopoly in American history, a textbook case for the need of Antitrust laws…Why Didn’t He Make the Final Cut? Rockefeller is a bit more ambiguous than some of the others on this list in terms of his life’s work. Although he oversaw a massive monopoly and popularized fossil fuels (the planet, surely, “thanks” him), his charitable works were considerable, and before him as much as 40% of oil run-off sludge was dumped in rivers. It’s not a good legacy, but too mixed to really include him in the Top 10.

13. General Charles LeeWho Was He? An early leader of the Continental Army, and a rival of George Washington’s to lead it during the American Revolution…Why Him? He was rumored to be a traitor of the Revolution, and secretly in the employ of England. If he had lead the Army instead of Washington, it’s very plausible the American Revolution would have failed…Why Didn’t He Make the Final Cut? You don’t know how badly I wish I could include him in the Top 10, but the truth is that we simply don’t know to what extent he was working for England. Plus, he was born in England, was a British citizen, and may not technically have been an American as citizenship was a bit murkier during the Revolutionary period. Still, although Benedict Arnold is the more famous traitor, there’s no question Lee would’ve done more damage overall.

12. Edward BernaysWho Was He? Sigmund Freud’s nephew who used his Uncle’s psychology techniques to invent subliminal advertising, public relations, and the “irrational consumer” who is swayed by modern advertising…Why Him? Some of his notable works include a campaign to topple the government of Guatamala on behalf of The United Fruit Company and a campaign to get more women to smoke by branding cigarettes “Torches of Freedom,” not the first time Big Business has co-opted progressives by presenting poison as empowerment…Why Didn’t He Make the Final Cut? He probably would have except he’s an Austrian-American immigrant. Regardless, I think he’s the figure most responsible for corporate brainwashing of American life, tapping into an emotional aspect that defies logic. His work has certainly been used by everyone from fossil fuels to cigarettes to climate change deniers.

11. Ray KrocWho Was He? The “founder” of McDonald’s who didn’t really found anything but the idea to franchise the greatest threat to public health since the Spanish Flu…Why Him? He swindled the McDonald brothers (the actual inventers of fast food) out of their company and fucked them on royalties. He divorced his first wife when he was nearly sixty and successful for the first time in his life, and left her without a single share of McDonalds stock. And he gave rise to the behemoth that began to symbolize the unholy hat trick of poor worker conditions (“McJobs” are still a synonym for low-paying, dead-end work), unhealthy products (you can’t sell cigarettes to kids, but McDonalds advertises right to them), and Big Business rolling over mom and pop stores…Why Didn’t He Make the Final Cut? Blame the movie “The Founder” in which Michael Keaton’s Ray Kroc is such a figure of pathos, he’s almost a Willie Loman-figure that actually finds success. It shows the Dark Side of the Underdog, but there’s no denying Kroc was an underdog, and it’s hard to fully root against someone who finds success late in life, no matter how shitty you believe them to be as a person.

If you’re curious to find out who the “Ten Biggest Assholes in American History” are, then check back throughout the week…


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