10 Toughest Gangsters In Crime History

“How you doin'?” It has always been a mystery as to why gangsters are revered the way that they are. For so many of them, they are not exactly pillars of their communities. Many of them rob, steal, and kill to get their way to the top of the underworld. A lot of gangsters are especially involved in the drug trade, further deepening many of the neighborhoods they came from into despair. These tough guys pay off cops, bribe politicians, and make small business owners pay for “protection” from outside influences. The worst part is that when many of them are caught, they sing like canaries, ensnaring their former friends and associates in their downfall.

But this does not mean that gangsters do not enjoy a legendary status. In these same communities they destroy, they are often looked at as heroes, philanthropists, and success stories of how a little bit of street smarts and hard work can pay off. In fact, most of the rap music industry has made its living on glorifying gangsters and the gangster lifestyle. Suffice it to say that being a gangster can be seen as cool.

Gangsters come in all kinds of colors, religions, backgrounds, and cultures. But being a gangster is not easy. Being a tough gangster is even more difficult. Being one of the toughest gangsters in history requires stories that are so unique that they cannot possibly seem real. However, for these 10 gangsters, their reputation precedes them and their legends will outlive them.

10 Sammy “The Bull” Gravano

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Few gangsters have a history of violence like Sammy “The Bull” Gravano. As a member of the Gambino crime family, Sammy went from a small-time crook to a big-time wise guy for the Italian mob in New York. What made Sammy so famous and earned him such an appropriate nickname stems from his thug mentality, ruthless brutality, and total lack of conscience. As a former hitman for the mob, Sammy orchestrated and executed some heinous crimes against some of his rivals, killing them without a second thought. Doing so helped eliminate the competition for years.

This was until Sammy turned into a rat and became a government witness. The FBI convinced Sammy to turn against his friends and helped bring down some of the most elusive and successful gangsters of the past 50 years including his friend John Gotti. Sammy went to prison and was ultimately released into the Witness Protection Program, moving to Arizona and attempt to start his life new. In true gangster fashion, Sammy got caught up in an ecstasy ring and landed right back in prison. Once a gangster, always a gangster.

9 Al Capone

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Nearly every gangster in history is compared to this legendary bad guy. Hailing from New York City, Al Capone was a little known criminal in the Big Apple. Capone then decided to move his “skills” to Chicago and begin working for the mob. What made Al Capone so tough was not that he was the tallest or even had the biggest muscles, but rather Capone’s ability to intimidate the hell out of his enemies and his friends.

Capone took advantage of the ill-fated prohibition on alcohol in the early 20th century by bribing police officers, aldermen, politicians, and citizens to keep quiet or else. He was a street tough, but he used his mind, his money, and his personality to get people to do his bidding.

8 Frank Lucas

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Throughout the 19th and 20th centuries, there was little room for African-American gangsters to gain any legitimacy. Rules, both formal and informal, kept many people of color from enjoying even the most basic things in life. African-Americans were kept from restaurants, hotels, and denied routine services like medical care. Even among criminals, African-Americans had trouble earning respect.

Enter Frank Lucas. For years, Frank was one of the most notorious drug dealers New York had ever seen. He used his business savvy to outsmart the rest of the competition by cutting out the middle man to get his drugs by shipping it from other countries in the coffins of soldiers returning home. Talk about guts. He amassed a fortune by doing business this way and even had a movie, American Gangster, made based on his life and was immortalized by Jay Z with an album of the same name.

7 Griselda Blanco

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Most women would not end up on the list of world’s toughest gangsters. The violence and looming possibility of death or prison seems to generally attract men to that field and women often find much smarter, safer ways to spend their time.

6 Pablo Escobar

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There may be tougher gangsters on the list than Pablo Escobar, but there are few that are nearly as well recognized. Pablo Escobar, one of Colombia’s most famous residents, was a drug lord that all drug lords are compared to. He orchestrated the deaths of a number of people, irrespective of their status. Police, rivals, and politicians were gunned down if they even appeared to be a threat to his empire.

Using the term “plata o plomo” (silver or lead), Escobar amassed so much power that even when he was caught, he built his own prison, La Catedral, when he was caught a few years before his death. A countless number of books and movies have been made about Escobar’s life and death that his legacy as a tough guy will live on forever.

5 John Gotti

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Most wise guys do not dress well. They have on their Adidas sweatsuit on or a polo shirt with slacks for special occasions. Not John Joseph Gotti. This guy dressed as sharp as a razor blade and earned the nickname “The Dapper Don.”

What made Gotti so tough is that the government could never pin anything against this guy. Gotti had masterminded the killing of a lot of his rivals, but people were so scared of him that many of them refused to testify or just claimed they did not know anything. It is real power when a person has the ability to give others amnesia.

4 Jack “Legs” Diamond

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Jack “Legs” Diamond would probably be an automatic member of 50 Cent’s G-Unit because of how tough he was. “Legs” was a typical bootlegger during Prohibition in the early 20th century. For a lot of thugs, the easiest way to make money was just simply running liquor for various outfits throughout the eastern part of the United States. What made “Legs” so tough was the fact that few gangsters had as many attempts on their life as this man. Even his biggest rival, Dutch Schultz, spent nearly 15 years trying to kill him, finally succeeding in 1931.

3 James “Whitey” Bulger

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Admittedly, “Whitey” is not the toughest of nicknames, but James J. Bulger needed very little to prove how tough he was. For those that are unaware, Boston, Massachusetts has a sizeable Irish population. Particularly in the southern part of the city, there is a strong Irish influence that has held strong for years.

The one man to run that part of the world was “Whitey” Bulger. “Whitey” not only involved himself in every aspect of the criminal underground, he also worked with the government to inform on his rivals. This kind of savvy, along with brutal killings, cleared the path for money and power he could have only dreamed of.

2 Stanley “Tookie” Williams

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For anyone that has been to Los Angeles, it is no wonder why gangs exist. The city is so big, so spread out, and kind of segregated by natural and artificial barriers. This kind of geography tends to create fierce loyalties to particular neighborhoods and, with such diversity, there is bound to be conflict. For years, most of the African-American gangs in L.A. were about joining something meaningful because many of the young men were kept from social clubs that excluded based on race. Violence was not a primary method of getting things done.

Stanley “Tookie” Williams changed all of that. “Tookie” brought a level of violence, drug use, and intimidation that the area had never seen and spawned a wave of gang behavior the world was not prepared for. “Tookie” was ultimately executed for being a convicted murder, but what was “Tookie’s” greatest claim to fame? He founded the Crips.

1 The Kray Brothers

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Almost all of the gangsters on this list are of American heritage. Even if their parents were born in Ireland, Sicily, or Italy, most of the gangsters went to American schools, grew up with American culture, or somehow became rich and infamous based on their American exploits.

The Kray Brothers, Ronald and Reginald, are probably the most notorious, dangerous, and infamous gangsters to never care about the United States. Who knows how they found the time between their robberies and kidnappings to run some of London’s most successful nightclubs during the 1960s. Their tough-guy attitudes could not even dissuade some of the world’s famous entertainers like Judy Garland or Frank Sinatra from staying away from their hangouts.

In their most famous incident, Ronald reportedly had a homosexual relationship with a conservative politician, but the papers were so afraid of the Kray twins that they not only backed off the story, they paid the politician money as a “my bad.”  The movie Legend was made to highlight their life. Simply untouchable.

Sources: NYDailyNews.com, Channel4.com, TheUndefeated.com

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