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15 Of The Most Ruthless Underworld Kingpins

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15 Of The Most Ruthless Underworld Kingpins

Organized crime isn’t what it used to be. The glory days, romanticized in television and film, have long since gone the way of prohibition, but not without allowing some of its most dangerous players to leave their bloody foot imprints on historians and enthusiasts alike. Sure, modern day mobsters exist, but the idea to publicly kill any human shaped obstacles is considered messy business. A necessary death does happen now and again, but these days it’s smarter to wet your beak in credit card fraud than it is to extort a local shop owner.

Still, if we look back through history we’ll find a steady pattern of men and women who have made their livings from businesses that are on the other side of legality, and to do that you need to be able to stomach more than a boring old murder, oh no, you need to be downright heartless. You need to not only be willing to turn your back on the three “Fs” (friends, family and faith), but also hold a loaded gun to their throat until they pay up like everyone else. To succeed in the criminal world and lead a team of scoundrels equally as cold as yourself, you need to be downright evil. I’ve compiled a few of them for you to read about. Here are history’s 15 most sinister underworld kingpins:

15. James Coonan

In 1966, James “Jimmy C” Coonan fired the first shots of his first gang war from the rooftop of a Manhattan tenement building when he was 20-years-old. Two years earlier he founded “The Westies”, a tough group of Irish-bred kids born out of New York City’s Hell’s Kitchen. Over the course of the next two decades, The Westies dominated the drug, extortion, numbers, loansharking and counterfeiting rackets out of Manhattan and even exclusively did hits for the Gambino crime family. Coonan was a stone-cold killer, make no mistake about it. He was famous for chopping up his victims and throwing them in the Hudson River. He even had his mentor, loan-shark Ruby Stein, murdered after a fair amount of his crew started stacking up debts to him (and then proceeded to collect the money for himself). But even hard-nosed criminals have their limits, and when Coonan’s right-hand man, Mickey Featherstone didn’t approve of their Italian mob ties, Coonan didn’t kill him, but rather framed him for murder; having another member of the crew dress up like Featherstone and shoot a man on a construction site. The stunt put Featherstone in cuffs until he figured out their little scheme and turned informant, putting his former best buddy, Coonan, away until 2063.

14. Nicky Louie

In the 1970s Yin Poy was better known by his street name, Nicky Louie. The young Chinese hood immigrated to America sometime in the late 1960s and quickly began his rise as the leader of the new order of Chinese crime in New York City. It’s literally impossible to find a photo of this guy, so instead I posted an image of a Chinese funeral home in New York City in the 70s. Which is fitting considering Louie founded the infamous Ghost Shadows gang of Mott Street in 1971 and aided in the killing of 13 people as well as attempts on many others. Authorities compared Louie and his Ghost Shadows to the mafia at the turn of the century – ragtag and ruthless. These were young kids dressed in second-hand army fatigues trying to squeeze out any bit of cash from the city they could no matter who got in their way. They often opened fire on businesses they thought were under protection from rival gangs and frequently killed bystanders caught in the crossfire. What makes Nicky Louie especially notable, is that rivals would shy away from his turf if they even caught a glimpse of him on the street. He was rumored to have nine lives, an assumption based on how many assassination attempts he had survived, and it was said that when he rolled over at night you could hear the bullets clanking together in his body. Louie did a ten-year sentence starting in 1984, but at this time is as free as a bird.

13. Al Capone

There’s really not much left to write about the most famous gangster who ever lived, Alphonse Gabriel Capone. But did you know he originated as a gang member in New York’s notorious “Five Points?” Yeah, the same five points from Scorsese’s Gang’s of New York, and did you know he managed to work all of his killing and illegal boss activity into a short seven-year span all before he was 33 years old? The Chicago crime lord, who at the time of his prohibition-era reign, was seen more as a Robin Hood figure than a crook, is most notable these days for eradicating his enemies or to be more accurate, the methods he took to eradicate them. After killing off rival Dean O’Banion, a war ensued, which Capone was eager to end. He instructed his men to tail and monitor the remaining members of their crew and on Valentine’s Day of 1929 Capone’s men, dressed as police officers, raided their hideout. Capone was summoned to court following the murders but didn’t show up claiming he had a stomach ache. That’s how easy it was to get out of court back then.

12. Louis Buchalter

Don’t let that smiling face fool you, this man was the founder and “CEO” of the infamous Murder Inc. Buchalter was born in Manhattan but spent most of his life in detention facilities well into his twenties. After that, he took control of New York’s garment district before starting a business the media would later call, Murder Incorporated. The basis of the business was simple, to keep their hands clean of any wrong-doing; mafia bosses would hire Buchalter who would then hire a run-of-the-mill street hood to carry out the murder. It was basically a hitman-for-hire business when at its height, was earning Buchalter $1 million a year ($17 million by today’s standards) with 250 men working under him, each ready to pull a trigger at a moment’s notice. The crap hit the fan, however after Buchalter knocked off a candy store owner who he thought was working with the district attorney. After that, Buchalter was on the run for several years before finally turning himself in. By 1944, they strapped him to the electric chair and plugged him in. From then on, mob bosses had to hire their own hitmen.

11. Semion Yudkovich Mogilevich

An AK-47 with a good education. That’s the best way to describe Mr. Mogilevich, the leader of the Russian mob wanted for drug trafficking, contract murders, international prostitution, and trading nuclear materials among other things. This plump little fellow is what happens when you give a gangster an economics degree… literally. Since his start as acting head of the mob, in the mid-1990s, “the brainy don” as he’s called, has shown his prowess without the confines of borders. Reportedly, he has factions in New York, Los Angeles, and New Zealand, and in 1998 he fraudulently built an entire Philadelphia-based company and traded it on the U.S. Stock Market – a scheme which netted him over $150 million without stepping a foot in Pennsylvania. It’s conniving schemes such as this one that garnered him the label of “the most powerful mobster in the world.” Also, because 30% of Europe’s gas comes from Russia, and who do you think runs the pipelines in the red country? You guessed it, Mogilevich. Aside from the criminal acts typically attributed to organized crooks, which Mogilevich is certainly guilty of, he extorts millions European working class people by holding their heat and stoves hostage. If that’s not sinister I don’t know what is.

10. James “Whitey” Bulger

Somehow, through America’s recent ten-year love affair with Boston’s popular culture and its centuries old infatuation with true crime stories, the legend of James Bulger has become the closest thing this millennium has to Capone. Starting off as a small time hood in South Boston’s Winter Hill neighborhood, Bulger steadily began rising in the ranks until he was running the show. He famously made a quiet deal with the F.B.I. and ratted out his enemies while he continued to kill and steal uninterrupted. This guy was pure evil. He even strangled his friend’s step-daughter because she spent a night in jail. In fear of her talking to the cops, he bailed her out and strangled her with his bare hands before ordering the aforementioned friend to bury her. When his reign finally crumbled and all of his associates flipped on him, Bulger ran and remained on the lamb for over twenty years until he was finally captured 3,000 miles away in Santa Monica, California. He went on trial for 32 counts of racketeering, money laundering, extortion, and weapons charges. The cherry on top was his complicity in 19 counts of murder. That’s a lot of burying.

9. Dario Antonio Úsuga, aka Otoniel

In recent years, Mexico has become the epicenter of drug trafficking, but before the business moved north, Columbia was the end-all-be-all in illegal substances most notably cocaine. And the country is still highly active in its production as well as methamphetamines in general. Dario Usaga, or “Otoniel” as he’s known on the streets, is the leader of one of Colombia’s largest drug trafficking organization and considered to be Colombia’s most prominent drug trafficker not behind bars. He and his cronies reportedly move close to two tons of booger sugar a week. That’s over $60 million (street value) of profit every seven days. Aside from warring with rival cartels, Usaga is known for hiring local street gangs to carry out extortion and assassinations for anybody who is willing to pay. Anything for a buck, right?

8. Nicodemo Scarfo

Having a Napoleon complex is a social issue that can cause unnecessary scuffles when you’re an average short guy in your group of friends, but imagine when you’re the leader of a deadly criminal organization. Nicodemo Scarfo, the head of the Philadelphia crime family in the early 1980s, was commonly referred to as “Little Nicky” as long as the don wasn’t in the room. Scarfo was known to be a psychotic narcissist who would murder a man for even looking at him the wrong way. So, with that in mind, it was best to refrain from calling him “little” to his face. This is what happens when a more current mob boss attempts to emulate the mafia heads of yesteryear. Scarfo idolized Al Capone and desperately tried to live the life of a celebrity gangster. He would order his soldiers to commit hits in broad daylight or in public and then scan the newspaper the following day for any mention of his name. Problem was, a life of crooked notoriety makes you easy to track, and by 1986 the feds sent Scarfo to the clink on extortion charges where he died 30 years later.

7. Salvatore Riina

This guy is old school. I don’t mean “old school” in the sense that he saw his prime in the era of prohibition, but rather in the sense that he never left Sicily to make his criminal riches. Riina had two nicknames, “la belva” (the beast) and “il capo dei capi” (the boss of bosses), and if you look at his resume you’ll find that both are extremely fitting. Riina came to power in the 1970s when Sicily became a docking point for the heroin trade. After becoming a major figure in the underworld he basically killed anyone and everyone as long as it meant he could proceed with his illegal activities. During a time in Sicily when mafia dons were present in the public eye, frequently seen with elected officials, Riina and his associates chose to stay hidden, that way when he murdered judges, police captains, and politicians, the media naturally pointed fingers at the men they knew had their hands in the pot. When soldiers in his faction eventually turned sides and authorities finally started building a case against Riina in the 1980s, he decided it would be best to divert the nation’s attention from his now-publicized wrong-doings so he organized a terrorist-style bombing of a train that killed 17 people and wounded another 267. Officials blamed the event on extremists and it wasn’t until many years later they realized the boss of bosses was the man behind the tragedy.

6. Osiel Cárdenas Guillén

You know you’re a bad hombre when your nickname is ‘The Friend-Killer’. Maybe it sounds more pleasant in Spanish. Guillen was a humble mechanic in Mexico who began helping Juan Garcia Abrego, the capo of the Gulf Cartel, ship drugs into the United States. After Abrego was arrested in 1996, the cartel was without a leader and obviously, the coveted title was a sought after by numerous potential successors. The two top contenders, however, were Guillen and his bestie, Salvador Gomez. But seeing no need to continue with politics, Guillen took the burden of deciding off the shoulders of others in the faction and put a bullet in Gomez’s head (thus the nickname). Under Guillen’s reign, the Gulf Cartel began recruiting ex-Mexican military to operate as a personal army and with their help, the cartel successfully moved 20 tons of cocaine a month. Eventually, Guillen’s story came to an end only a few years later in 2003 when, after a very long and very bloody shootout with the actual Mexican military, he was arrested and extradited to the United States where he was sentenced to 25 years in prison.

5. Dawood Ibrahim

Being the head of an illegal international banking system, killing hundreds, and having ties to Osama Bin Laden are but a few of the reasons that put Dawood Ibrahim on World’s Ten Most Wanted List. He’s alleged to be the head of a criminal organization known as “D-Company” as well as the controller of the hawala system. What is the hawala system you ask? Well, have you ever wondered how money moves from one criminal organization to terrorists and back again without being traced by any government whatsoever? We have the hawala system to thank for that. Aside from pulling the strings on what some readers may think is a boring white collar scheme, Ibrahim is also believed to be the mastermind behind the 1993 Bombay bombings, which if you don’t know, were a series of massive explosions in Bombay that killed 257 people and injured another 717, and went down in history as the most destructive in the history of India. So, yeah, this guy isn’t as prim and proper as his banking schemes may make him seem.

4. Griselda Blanco

Known as “The Black Widow” and “The Cocaine Godmother,” most people know Griselda Blanco for stealing the show in the documentary, Cocaine Cowboys. And while some will lead you to believe Pablo Escobar was responsible for all the coke Miami snorted up in the 70s and 80s, in truth Blanco had a great deal to do with pioneering the notorious operation. Born in Columbia, Blanco moved to New York City with her husband in the early 1970s and after establishing one of hell of a cocaine business out of Queens she fled back to Columbia once NYPD tried taking her down. She settled in Medellin before moving back the U.S. a little before 1980. During this time she ran one of the largest cocaine distribution operations in history and also spearheaded one of the deadliest drug wars in United States history. Her business reportedly spanned across the entire nation and earned her a staggering $80 million every month. However, by 1984 Miami officials had had enough of the violence and did their best to slap cuffs on Blanco, but being the slippery little devil she is, she fled to California before they could nab her. The DEA caught up with her a year later and tried convicting her for three murders despite her body count being estimated closer to 200. She remained behind bars, where she somehow continued to run her illegal business, until 2004 when her case fell apart and she was deported back to Columbia. Not much else was heard from Blanco until 2012 when a gunman on the back of a motorbike put two bullets in her head. She died outside of a butcher’s shop at the age of 69.

3. Sandra Avila Beltran

Sandra Beltran, or “The Queen of the Pacific” as she was known as in the media, was born into the organized crime business. One of her uncles is doing a forty-year bid for killing a DEA agent and another uncle was the former head of the Guadalajara Cartel, so she’s basically a third generation drug trafficker. She was allegedly the link between the Sinoala Cartel and America. And even though she employed violent tactics to put an end to her enemies no matter how large or small (her two ex-lovers – police captains turned traffickers – were each mysteriously assassinated) and authorities traced nine tons of cocaine back to her, she was able to avoid arrest well into the 2000s until her son was kidnapped. Desperate to have him returned, she actually asked the police for help, and they did, and then promptly arrested her immediately after because, you know, the drugs and the murder. Since then she served time in Mexico City where she received on-call botox shots and complained about prison conditions. She was released in 2015 is presently free to continue the family business.

2. Frank Lucas

In the late 1960s the United States was a country torn apart politically. Young people were protesting the government while our troops were getting slaughtered in Vietnam in what was the first televised war, and one Harlem resident was profiting off of all of it. Frank Lucas was a good ‘ol boy from North Carolina before he moved to the big city and worked as the right hand man for notorious gangster, Bumpy Johnson. After Johnson’s death, Lucas decided to take the wheel but was tired of getting pushed around by middlemen when it came to his heroin business. Instead, Lucas went right to the source. He traveled to Thailand, where the heroin was being manufactured, and struck a deal that would cut out any wholesale surcharges. How do you get tons of heroin from Thailand into the United States without anyone batting an eye? Lucas devised a plan in which he smuggled the drug in the caskets of dead U.S. troops being flown back home to be buried. As grim and horrible as that may seem, the scheme reportedly made him an average of $1 million a day. Lucas was eventually arrested and turned informant and he’s still alive to talk about his endeavors to this day.

1. El Chapo Guzman

Joaquin “El Chapo” Guzman is the most successful, most dangerous, and most powerful drug trafficker planet earth has ever seen (yes, even more powerful than Pablo Escobar). The head of the Sinaloa Cartel made Forbes Magazine’s “most powerful people” list three years in a row, he was the tenth richest man in Mexico with a fortune valued at $1 billion, and the federal government called him “the most ruthless, dangerous, and feared man on the planet.” Guzman made his bones in the 70s managing shipments as an underboss. It’s been said if a delivery was even minutes late he would shoot the messenger in the head. He rose in the ranks and was arrested in 1993 but bribed his way out of his cage and became one of the few people to ever escape from a maximum security prison. He was caught again two decades later, but not before he chopped off the head of his enemies… literally. In 2014, El Chapo was put behind bars again, but he made a laughing stock out of officials when he managed to escape a second time. This time through a handmade tunnel dug out of the showers. In 2016, Guzman was finally caught once and for all and extradited to the United States where he awaits trial. At least… as of now.

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