Boss Tweed.

Al Capone.

Billy The Kid.

Jesse James.

Jim and Tammy Faye Bakker.

Leona Helmsley.

An example of villains who prey on the elderly:

Scammers Leave 82-year-old penniless

Actually, he only shot one that we know of.

Here's a nomination: Thomas Edison

Some nominations:

William Bryant and Francis May

Who?

William Bryant and Francis May were the owners of the Bryant and May Match Company. For quite a while, if you were a smoker you had Bryant and May matches in your pocket. Also the blood and tears of children.

Why They Were A hole Bosses:

Look, if you ever have a chance to take a job that requires you to first travel in a time machine to Victorian era England, don't do it. This is Scrooge era here, when filthy children roamed the streets, eating rats and doing adorable song and dance numbers.

So how crappy of a boss did you have to be to become the subject of huge public backlash in those days? Let's examine the Bryant and May method.

First, you hire nothing but young, teenage girls. There were plenty of them around, they had no other opportunities, and they weren't likely to beat you down with lead pipes when they got fed up with your crap. You work them 12 hours a day, and pay them in the neighborhood of four shillings a week (the equivalent of $20... in today's money).

Since forcing the workers to scrape by on quite a bit less than what it costs to buy food still wasn't keeping morale quite low enough, they imposed a series of petty fines for a long list of offenses--everything from going to the bathroom without permission, to having dirty feet. When one girl let a machine jam up rather than have it tear off her finger, she was told the machine was more important, dammit, and to never let it happen again. When another girl did get her hand mangled, she was given the boot. Can't make matches one-handed!

However, Bryant and May couldn't help but notice the other match companies were still making more money. What were they doing wrong? Clearly they weren't abusing their employees enough... was there some kind of torture device they could be using? Maybe if they just let wild badgers run loose on the production floor?

They had a better idea. They had been making their matches with the extremely flammable but otherwise safe red phosphorous. But there was this other kind, white phosphorous, that was way cheaper. And there was absolutely no downside.

Oh, except it would literally eat your face off when you handled it.

Seriously. They called the condition phossy jaw. It was caused by breathing the fumes for too long. The symptoms start with toothache, which led to swelling, abscesses and then a putrid discharge caused by your jaw bone actually rotting inside your head.

Then your jaw would actually start to glow green. It freaking glowed. The only treatment was jaw amputation, which had to be done before organ failure killed the victim.

Keep in mind, Bryant and May knew this; white phosphorous matches and the corresponding side effects had been around for decades. The girls at the factory finally went on strike, figuring horrifying deformities were the final straw. The whole "glow in the dark face-rot" won the sympathy of labor activists at the time, and the women eventually won the right to experience something less than David Cronenberg-levels of horror at their workplace.

The Bryant and May company, of course, stayed in business for decades and made its owners huge amounts of money.

Candidates #2: Max Blanck and Thomas Harris

Who?

Max Blanck and Thomas Harris were the owners and operators of the Triangle Shirtwaist Company, which made lady's blouses. Why blouses are called "shirtwaists" is lost to time, if by "time" you mean us not caring enough to go check. Did they only make the waist part of the shirt? We'll never know.

Why They Were A hole Bosses:

Blanck and Harris employed an almost entirely female workforce for the same reasons as Bryant and May: young, many of them immigrants, all with nowhere else to go. They paid six or seven dollars a week (again, crap money even in 1909) and when workers walked out demanding better conditions, the pair hired thugs to beat the crap out of them. When the garment workers' union finally came to an agreement with other manufacturers, Blanck and Harris said hell no.

On top of all this, it seems like a minor thing that they also locked one of the main factory exits from the outside, to supposedly prevent theft by employees. Minor, you know, unless there's a fire. But why would there be a fire in a factory full of machines, strips of dry cloth, tissue paper and smokers? Where there had been fires twice before?

On March 25, 1911, the inevitable happened. Some women made it out before one exit filled with smoke and flame. Others made it onto the fire escape, which collapsed. The rest were trapped inside, banging on that locked door, while they were cooked alive.

All told 146 people died, the worst fire in New York history (a record that would stand all the way until 9/11).

Blanck and Harris were charged with manslaughter. Luckily for them they had way more money than the plaintiffs, and they hired Max Steuer, the Johnny Cochran of his day. He tore apart the testimony of the survivors, hinting that the whole thing was a conspiracy by the evil labor unions, and that no one could prove the door was actually locked. Sure, they found the lock in the burned out rubble, still very much in its locked state. But couldn't it have been tampered with? By the unions

Blanck and Harris got off. But Blanck was arrested two years later for--get this-- locking his freaking workers inside another factory. Holy crap!

They had his butt now! Justice would be served! Oh, wait, no. He was fined $20.

But wait! Twenty-three families did successfully sue over the Triangle fire and won... $75 each. So, that's sort of justice, right? That's almost 2,000 bucks right there?

Wait, did we mention that Blanck and Harris filed a claim with their insurance after the fire? And got $60,000?

I refuse to read that, can you pls just tell me?

+1 for John Wilkes Booth.

Al Capone?

I don't think this passes rule no. 1. But then, I don't really like rule no. 1. I've always preferred complex and sympathetic villains over one-dimensional, outright monsters.

So I'm going to go with Robert E. Lee, someone who wasn't a bad man, and by all accounts was only acting out of a sense of loyalty and duty to his home. Nevertheless, he was most powerful figure in the Confederacy, which was the greatest threat this nation has ever faced outside of Britain and Nazi Germany.

You could also make an argument for Jefferson Davis, but I don't think he defined the Confederacy like Lee did.

Mark Chapman

Dick Cheney

/thread

It also is in violation of Rules #2 and #4. FAIL.