originally published April 21, 2014

On June 29, 2009, District Judge Denny Chin sentenced Bernie Madoff to a whopping 150 years in prison for defrauding thousands of investors and ripping off more than $65 billion for his own pocket from people who presumably actually worked for that money. Madoff had committed an act of wickedness that would make any Bond villain shake their heads in filthy humbled admiration, but Judge Chin’s sentence was a headline unto itself. The federal probation office had suggested fifty years. Madoff’s lawyers had asked for twelve.

At the time, I questioned the reasoning behind sentencing a 70-year-old man to 150 years in prison. Fifty would have been plenty to ensure he died behind bars, even if Bernie had been spending giant globs of that $65 billion on youth-juice injection treatments. One hundred years would have been sufficient to deliver a message to any would-be Ponzi-cookers out there that the benchmark standard for such schemery was death in the joint, even with time off for good behavior. But 150?

It’s a glorious fuck-you to Madoff’s great-great-great-great grandkids, a permanent etching of shame upon the family name. But even as far as prison sentences go, Madoff’s lengthy booking is far from the longest ever handed down. His crimes may have been more despicable than those committed by some of the others on this list, but I guess it’s all a question of who you piss off.

Velupillai Prabhakaran had a dream. He wanted to create a peaceful Tamil state just northeast of Sri Lanka, a gift unto his people, albeit with himself as the corruptible, mustachioed leader-for-life. He founded the Tamil Tigers, an organization dedicated to achieving this goal through violent means if necessary (which, as it turned out, was constantly necessary). 32 countries called Velupillai’s organization a terrorist group. After an unsuccessful attempt at peace talks broke down, Velupillai was killed in a clash with the Sri Lankan army.

But long before that, he was found guilty of plotting the 1996 bombing of the Central Bank Building in Colombo, an act that killed 91 people and injured around 1400. He was sentenced in absentia though, meaning the 200 years he was handed were on a just-in-case-we-ever-catch-him basis.

When Jeffrey Kollie and Ryan Brandt were ordered to spend seven consecutive life sentences (that’s about 265 years if they behave) for armed robbery in 1996, it was the longest sentence ever given out by the state of Georgia. The two had committed an armed robbery, breaking into a family’s home, shooting the husband, tying up the wife and threatening their six-year old so that they could sneak away with the couple’s ATM cards. A few weeks later, they held up a restaurant, stripping down the customers and staff and tying them up with duct tape before enjoying some drinks at the bar.

Had they pled guilty – and with that many witnesses, how could they not? – they would have received forty years apiece. The lesson here is that one should avoid being an asshole when on trial for a crime one has obviously committed.

Norman Schmidt’s sentence in 2008 must have made ol’ Bernie quiver in his state-appointed prison boots a little. The extent of Norman’s fraudulent investment practices only stretched into the millions, not the billions. Yet he was handed a term of perpetual incarceration that would keep him locked up until sometime between the events of Star Trek and Star Trek: The Next Generation: 330 years.

Sholam Weiss’ particular fraud went after the National Heritage Life Insurance company. He drained the company of around $450 million, leaving its bloody corpse to rot in the sun. The FBI considered it the largest single act of insurance fraud ever committed and even dropped Sholam onto their most-wanted list for a while. He was extradited from Austria in 2000 and sentenced to 845 years in a high-security facility, meaning that the toughest of hoodlums will be doing to Sholam what he had in effect done to that insurance company, over and over again.

When the dictionary is rewritten with pretty pictures, you’ll spot Ariel Castro’s mug beside the definition of EvilMotherFucker (which is a word I’m hoping lands in the official lexicon around the same time). Castro kidnapped three women between 2002 and 2004, and kept them locked up until 2013, torturing and raping them whenever the mood struck. One of his victims, Amanda Berry, became pregnant and had a child with Castro, with the birth occurring roughly six years before the girls’ eventual rescue.

There is absolutely no question that Castro was guilty of the 937 charges levied against him. As such, he pled guilty to everything, including the aggravated murder of an unborn child when he beat up one of his pregnant captives. When the judge sentenced him to life without parole plus 1000 years, the system appeared to be working – justice was carried out. Then, just one month later Castro fashioned a noose out of his bed sheet and hanged himself in his cell, thus depriving himself of the years of suffering he so richly deserved.

By most accounts, Darron Bennalford Anderson was a sick and twisted son of a bitch. An Oklahoma judge looked at Darron’s rap sheet, which included the rape of an elderly woman in Tulsa County and a smorgasbord of larceny, robbery and kidnapping efforts, and handed Darron a sentence of 2200 years in prison. Darron’s defense team pushed for an appeal and a re-trial. Undoubtedly to the disgust of his victims, he won. A new trial was scheduled.

It turns out that the push for a new trial might have been a tactical error on behalf of Darron’s legal team. The new judge bumped the sentence up by nine millennia, for a new total of 11,250 years. It was the heaviest sentence ever imposed as the result of an appeal. Once again, don’t be a dick in court.

This is just the surface of how mightily the criminal justice system will smack its foes when necessary. Sure, most of these sentences were handed down in the United States, but that’s just how it is. I suspect most other countries, when they want to lock someone up for the rest of their lives rather than execute them will simply call it life imprisonment, with no time off for being a nice guy in prison.

But we’re sitting at 11,250 years at the top of this list, and this list goes much further. Tune in tomorrow for the deepest pits of incarceration.

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