Al Capone
Al Capone was a quiet, unassuming Italian-American boy born in Brooklyn in 1899. During his lifetime he would seize power of a major Mafia outfit, rule the streets of Chicago and compile a criminal empire so large and all-encompassing that his name will forever be synonymous with badass mafia motherfuckers who would just as soon pop a cap in your balls as spit on you.
As a young man, Capone was involved mostly in petty crime and local street gangs on the streets of Brooklyn, New York, beating up kids for their lunch money, fencing stolen goods on random street corners, and doing all manner of unsavory crap that would land most punks in juvie these days. At the age of fourteen, Capone was expelled from school for punching a teacher in the face (presumably because the teacher was being a fucking jackass), and he joined up with the Five Points Gang under the command of a dude name Frankie Yale. Yale saw that Capone was a ruthless badass that was not to be fucked with, and gave him work as a bouncer and a bartender at Yale’s numerous speakeasies and bordellos. Capone was right at home in his newfound job checking IDs, standing in the corner with his arms folded, looking as intimidating as possible, and punching the shit out of drunk assholes who didn't realize that there is no sex in the Champagne room. One night, Al received a huge scar on his face when he tried to bounce five rowdy, insane ninjas wigged out on PCP from a hot nightclub. Capone bashed those jerks in the neck with a baseball bat and the broken-off leg of a wooden bar stool until they were all pummelled unconscious, but during the battle he took a shuriken to the cheek that left him with a permanent mark of badassitude and a totally sweet gangster nickname – Scarface.
In 1919, shit got a little too hot in the Big Apple for Capone. He was under investigation by New York’s finest for two different murders, and a rival gang was after him because Capone had beaten one of their top lieutenants up so bad that he had to be hospitalized for two weeks. Frankie Yale sent Capone to work under a guy named Johnny Torrio in Chicago, where Capone would be placed in charge of the two rackets that would serve as the foundation of his criminal empire – prostitution and bootlegging. From this point on, Al Capone’s life pretty much became a real-life game of Grand Theft Auto III, only instead of running hookers over with his car and then beating up their dead bodies with a baseball bat, he was pimping them out for a shitload of money and paying his mafia wiseguys to illegally obtain large quantities of booze so he could sell it at three thousand percent profit.
Initially, most of Capone’s actions were taking place in the suburb of Cicero, Illinois, which served as his base of operations. He quickly became such a powerful and influential man that he completely took over the Cicero government and the police force though ruthless extortion and bribery. His men took control of the election polls, got Capone’s ally elected mayor, and then during the inauguration ceremony Capone punched the mayor in the fucking face and threw him down the steps of city hall just so everyone would know who the real power in the city was. Some dumbass rival outfit known as the O’Donnell Gang tried to carve out a piece of Capone’s criminal fiefdom, but a bitter gang war left over 200 dead and Capone’s Outfit in command of all criminal enterprises in Cicero. That's why you don't fuck with the family - because the Family will shoot you in the face with a drum full of .45 caliber ammunition and then use the empty gun to beat the carp out of all of your friends.
Incidentally, that last line was supposed to read, "beat the crap out of all your friends", but I think I prefer the typo.
Torrio retired in 1925 after a failed attempt on his life, leaving Al Capone in charge of one of the largest gangs in the Chicagoland area. The enterprise racked up over ten million dollars a year in bootlegging alone, which might sound like a Dr. Evil miscue today but was actually a fucking shit ton of money back in the 1920’s. Capone was untouchable by the police thanks to his ability to bribe, extort, and outright threaten the entire force, he was unhittable by rival gangs thanks to his constant escort of badass Tommy Gun-toting Mafioso motherfuckers packing more heat than a hazardous materials transport loaded up with molten hot liquid magma, and he rolled around town in a pimp-tastic bulletproof Cadillac with run-flat tires, a police siren, two heavy machineguns mounted on the hood, four cupholders, a plasma-screen DVD player, some crazy hydraulics and a built-in mini-fridge stocked with bourbon and scotch. His main base of operations, the Lexington Hotel, was populated entirely by gangsters loyal to the Outfit, and in only a few years of masterminding a criminal enterprise more powerful than anything Batman has ever seen, Capone had become so famous and notorious that his "hideout" was a stop on all major Chicago tour bus routes. Capone also had numerous bases located across North America, ranging from Saskatchewan to Miami, and encompassing everything in between. He had all the money, women, and power that any man could imagine, and despite his legacy as an evil, hardcore, Tony Soprano motherfucker, Capone also funded and ran free soup kitchens to help out the poor during the Great Depression in the early 1930s. So he wasn't all bad. Just mostly.
Of course, when you’re the fucking top dog everyone wants to get a cut of your action, and even the great Al Capone was not immune to this. A rival group of hooligans known as the North Side Gang under the command of an evil bastard known as "Bugs" Moran fought a near-constant turf war with Capone’s Outfit in the late twenties. Tommy Guns and fedoras tore up the streets of the Windy City as vicious underworld warfare raged throughout Chicago, killing more gangsters than the Tupac-Biggie feud. Capone himself had several attempts made on his life, including one time when a caravan of ten black cars loaded up with machinegun-toting hitmen drove by his hotel with their weapons blazing. Eventually, Capone decided it was time to end that shit. On Valentine’s Day of 1929, several of his men dressed up as police officers, rounded up some of the North Side Gang’s highest-ranking lieutenants and went nuts on them with Thompson submachine guns and large-gauge shotguns. Seven of the North Siders’ top men had their heads exploded, and Bugs Moran was on the run. The power of Capone’s enemies had been broken, and the Outfit had free reign over Chicago's bootlegging operations from that point on. No one was ever prosecuted for the crime.
Eventually, Capone was busted for tax evasion by hardcore Internal Revenue agent Eliot Ness and his crew of “Untouchables”. Despite ordering numerous murders and running some of the largest criminal rackets in the history of the United States, Al Capone was shipped off the fucking Alcatraz for failing to claim illegally-obtained profits on his goddamned income tax return. The fucking IRS will screw you every single time. Just remember this the next time you're trying to lie on your fucking 1040EZ - if you don't claim all the proceeds from your illicit prostitution and numbers rackets, the fucking Service is going to send a half-dozen highly-trained German Shepherd attack dogs to ring your doorbell and bite you in the scrotum when you open the door. After prison, Capone retired to the Miami area, where he eventually died of a heart attack at the age of 47.
Al Capone was one of the most hardcore, notorious, balls-out criminal masterminds in American history, and to this day his legend stands as a testament to what it means to be a badass motherfucker who takes no shit and gets whatever he wants, no matter how many people he needs to eliminate in the process. This was not a man you messed with if you wanted to remain alive.