Top 15 Longest Prison Sentences Ever Issued

Heading into a period of election-related banter, prison reform and justice issues are becoming popular as campaign promises these days above and below the Canada/United States border. In Canada, basically every party except for the Conservatives have said that marijuana will no longer be a criminal issue, but down in the U.S. given that party leaders have yet to be chosen, members of both parties are taking various stances.

Some are arguing for full legalization, others for decriminalization of small amounts, while quite a few are arguing to keep the status quo. Of course, it's a state issue, but plenty of Presidential candidates have suggested using federal power to disregard those states that decide to decriminalize the drug. Many of the same want to continue to lock up giggling potheads for decades over a plant that makes people laugh at stupid movies and eat obscene amounts of potato chips. What a time to be alive!

On the topic of drugs and prison sentences, one popular topic is mandatory minimum sentencing. It is the idea that certain crimes require a certain prison sentence at the very least, regardless of other considerations. It has been applied to drug crimes for a long time and is growing increasingly unpopular due to the fact that non-violent "offenders" could be thrown away for victimless crimes to rot in prison, an experience that hardens many people and costs an obscene amount of money. Twenty-five years for pot is nothing compared to some of these, however. Here is our list of the fifteen longest prison sentences ever issued.

Honorable Mention: Gabriel March Grandos: 384,912 Years (requested sentence)

Grandos was a mailman in Spain back in the 1980's. He was charged with not delivering thousands of letters, and the prosecution sought a period of time behind bars for every single one of them. It totaled over 300,000 years. The judge deemed that fourteen years would be enough.


15 Darrell Wayne Delp: 755 Years

Our first entry is Virginia's Darrell Wayne Delp, who was sentenced 755 years for various child sex crimes. According to investigators, he had well over 5,000 pictures, some involving children under the age of ten. Prosecutors added, when discussing Delp, that he was unrepentant and argued that there would never be a chance of rehabilitation in a case such as his. They asked that he never be let out of prison and the judge made it happen.

14 David Hall: 825 Years


Floridian David Hall, is our number fourteen. In 2014 he was arrested under suspicion of having posted sexual pictures online of young children. He was charged and convicted of ten counts of promoting such filth and 45 of possession.

He was sentenced to the maximum fifteen years for each of his charges, coming out to 825 years. It was not his first offense, as he had been locked up in the late 90's for a similar charge. The judge who issued the sentence called him a sexual menace and added that he had preyed upon children as young as four.

13 Sholam Weiss: 845 Years

Enough of the kid crime offenders for a bit, Sholam Weiss was a businessman who committed one of the most notorious acts of insurance fraud in history.

He was involved with the collapse and looting of the National Heritage Life Insurance Company, which occurred in 1996 and 1997. He managed to escape the United States for about a year but was found in Australia and extradited. While white collar crime is often treated with more lenience than violent offenses, nobody was messing around with sentencing for Weiss.

12 Ariel Castro: Life in Prison (Plus 1,000 Years)

Another recent case, and once again, one that may induce vomiting and nausea, Ariel Castro was the subhuman who confined three young women for over ten years in his basement. They were starved, assaulted, you name it. These three young women endured horrors one wouldn't wish on their worst enemy. As the writer, I'm supposed to remain impartial, but when Ariel Castro hung himself a few weeks into his life plus a millennium sentence, I (and probably many others) thought it was far too good a fate for such a person.   

11 Juan Corona: 25 Life Sentences

Known as the "Machete Murderer", Juan Corona was a Mexican-American labor supervisor in California, back in the 1970s. He hired migrant workers from Mexico to work, produce fields and for a couple of months in early 1971, he murdered 25 of them, and buried them in shallow graves. He was convicted of 25 life sentences, but the total amount of victims is believed to have been higher. Corona has been up for parole a few times, but was most recently denied in 2011. He is eligible again in 2016.

10 Bobbie Joe Long: 28 Life Sentences Plus Four 99 Year Sentences and a Death Sentence

Bobbie Joe Long is a serial killer, sexual assaulter and kidnapper from Florida who is currently on death row. Back in 1984 he tortured and murdered over ten women in Tampa. He would go out at night, searching for solitary women, particularly strippers or prostitutes, and after persuading them to come back to his apartment, would overpower them, and sadly, we all know how the rest would go.

He has remained alive through an extensive series of appeals, but remains on Florida's death row.

9 Martin Bryant: 35 Life Sentences and Over 1,000 Years

The Port Arthur Massacre is the largest mass murder in Australia's history. It served as a catalyst for firearm restrictions in the country. Bryant is now known to be terribly unintelligent overall. He suffers from significant learning disability and has an IQ in the mid-60's range. Doctors have said that his lack of reasoning ability was a contributing factor to the massacre he carried out in 1996.

He killed 35 people and injured 23 more with a pair of assault rifles back in that year and received a sentence that the judge hoped will keep him in prison for life, no matter what. He has attempted suicide many times while incarcerated.


8 James Eagan Holmes: 12 Life Sentences Plus 3,318 Years

The most recent entry on our list is James Eagan Holmes, the Colorado theater shooter. Back in July 2012, he entered an Aurora, Colorado movie theater and gunned down twelve people, injuring 70 more.

He was a student at the time, studying neuroscience, and was thought by many to be a little mentally "off". He was convicted of first degree murder and received the sentence of life without parole. The judge tacked on over three millennia due to the numerous attempted murders.

7 Two Iranian Conmen: 7,109 Years

There are no names offered up for this entry unfortunately, nor is there any significant information as to what kind of con these gents managed to pull off. Iran (and much of the Middle East) is not known for leniency for crimes. These guys were sentenced to over 7,000 years back in 1969, with the judge saying that he gave them a year for "every one of their transgressions".

6 Dudley Wayne Kyzer: 10,000 Years

Kyzer is an Alabama man who killed his ex-wife, mother in law and a male student back in 1976. Due to the fact that the murder took place on Halloween, he is known as the 'Halloween Killer'. He shot his ex-wife Emily, in the chest, Eunice, the mother-in-law, in the head while she tried to call the cops, and the student Richard Pyron, was shot in the head while begging for his life.

The criminal system couldn't kill him, so the judge sentenced him to 10,000 years so that he would never be free again.

5 Darron Bennalford Anderson: 11,250 Years

Darron Bennalford Anderson was convicted in Oklahoma of sexually assaulting an old woman, along with other crimes such as larceny, robbery and kidnapping back in the mid-90's. His original sentence was just over two millennia, but after an unsuccessful appeal, in 1997, he was later convicted once again, and this time was sentenced to 11,250 years behind bars.

4 Allan Wayne McLaurin: 21,250 Years

Allan Wayne McLaurin was Darron Bennalford Anderson's accomplice for any of the crimes for which he was convicted. He was convicted of most of the same things and received a 21,250 year sentence which was reduced by five centuries after a successful appeal. As previously detailed, he and Anderson deserved every single year of both sentences.

3 Charles Scott Robinson: 30,000 Years

Charles Scott Robinson is the highest American on this list, and he sure earned his thirty millennia behind bars. From Oklahoma, Robinson was convicted of six counts of sexually assaulting children back in 1994. The judge who issued his sentence made a point of creating a situation whereby no matter if Robinson was paroled for one of his convictions (after 13-15 years), he would have to wait well over 75 years to actually get out of prison. The jurors in the case were unable to have him sentenced to life without parole, so the judge took care of it.

2 2004 Madrid Bombers: (Three Men) Between 34,715 and 42,924 Years

Back in 2004, 191 people were killed and nearly 2,000 people were seriously injured when a small terrorist group inspired by Al-Qaeda detonated explosive devices in Madrid's train system. Jamal Zougam, a Moroccan living in Spain, was implicated with having sold the cell phones that detonated the bombs, as well as having a part in building them. Emilio Trashorras was sentenced to 34,715 years for supplying the dynamite, and Otman El Ghanoui was convicted and sentenced in connection with the bombing as well.

Others were also convicted but received much smaller sentences.

1 Chamoy Thipyaso: 141,078 Years

Chamoy Thipyaso is essentially Thailand's equivalent to Bernie Madoff. While Madoff got 150 years for his pyramid scheme, she received a sentence of 141,078 years in prison. She tricked over 16,000 Thais in a scheme that was worth over $200 million at one point.

She was discovered and tried back in 1989. The wife of a high ranking officer in the Thai Air Force, she set up her investment firm years prior to being caught along with seven of her accomplices.



More in Most Shocking