1. Michael Malloy
“Basically this dude was a drunk homeless guy living in New York City during the 1920’s I believe. His five “friends” all took out life insurance policies on him and then preceded to give him unlimited drinks at their bar, hoping he’d die of alcohol poisoning. When day after day he’d wake up and come back for more drinks, they swapped his alcohol with antifreeze. He drank this for multiple days before they switched it to turpentine, and then straight up rat poison. Yet still he’d come in, drink the rat poison until he passed out, and then wake up the next day to drink some more. Eventually they got tired of this and began feeding him sandwiches with tacks and broken glass in them, which he happily ate. Sick and tired of losing money trying to kill mike, they gave him drinks until he passed out, dumped him outside in a snow bank, and soaked him in water, assuming that he’d freeze to death. Yet the next day, here comes mike strolling into the bar asking for a drink. So they then proceeded to run him down with a car at 45 mph, abandoning mike in the street. Mike was moved by authorities to a hospital where his broken bones were treated to. They thought he had died and went to collect the insurance money, however the company informed them that they could not. Three weeks later mike, at this point out of the hospital, strolled into the bar, asking for a drink. So, finally, they got him all drunk and unconscious and ran a tube pumping gas down his throat. He died after nearly an hour of being suffocated.” — Quail_eggs_29
2. Balthasar Gerard
“At his trial, Gérard was sentenced to be brutally – even by the standards of that time – killed. The magistrates decreed that the right hand of Gérard should be burned off with a red-hot iron, that his flesh should be torn from his bones with pincers in six different places, that he should be quartered and disemboweled alive, his heart torn from his bosom and flung in his face, and that, finally, his head should be taken off.
Gérard’s torture was also very brutal. On the first night of his imprisonment Gérard was hung on a pole and lashed with a whip. After that his wounds were smeared with honey and a goat was brought to lick the honey off his skin with his sharp tongue. The goat however refused to touch the body of the sentenced. After this and other tortures he was left to pass the night with his hands and feet bound together, like a ball, so sleep would be difficult. During the following three days, he was repeatedly mocked and hung on a pole with his hands tied behind his back. Then a weight of 300 metric pounds (150 kg) was attached to each of his big toes for half an hour. After this half hour Gérard was fitted with shoes made of well-oiled, uncured dog skin; the shoes were two fingers shorter than his feet. In this state he was put before a fire. When the shoes warmed up, they contracted, crushing the feet inside them to stumps. When the shoes were removed, his half-broiled skin was torn off. After his feet were damaged, his armpits were branded. After that he was dressed in a shirt soaked in alcohol. Then burning bacon fat was poured over him and sharp nails were stuck between the flesh and the nails of his hands and feet. Gérard is said to have remained calm during his torture. On 14 July 1584, Gérard was executed.” — Ua_Tsaug