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When a millionaire gave everyone in a Florida neighborhood free daycare and free college scholarships, the crime rate was cut in half and the graduation rate jumped from 25% to 100%. He did this after being fired from Walt Disney World because his bosses didn't think he could be a 'company man'

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One of New York’s first crime bosses was a Prussian immigrant known as Mother Mandelbaum. She built up a criminal empire worth millions, ran a school to teach kids how to become successful pickpockets and thieves, and functioned as one most prominent hostesses for New York’s high society.

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Jake Adelstein, a Jewish-American reporter who investigated the Japanese crime world for over a decade, convinced some of his underworld allies and former yakuza bosses to play Yakuza 3, a video game where you play as a former member of the yakuza. The former bosses ended up loving the game.
The reason the suffix 'gate' is tacked on to every scandal is because of William Safire, a speechwriter for Nixon and a political commentator at the NYT, who began affixing all scandals with -gate in the belief it would make his boss’s crimes seem less severe in the light of history
Bernie Madoff's best friend in prison is Carmine John Persico Jr., boss of the Columbo crime family, who is serving 100+ years in the same prison
The longest running Massachusetts state senate president was forced to resign from a post as president of the University of Massachusetts after he refused to testify before a Congressional hearing about communications with then-fugitive brother, James "Whitey" Bulger, Jr., a Boston crime boss.
Oscar Goodman was the defense attorney for some of Vegas’ most notorious crime bosses including Meyer Lansky and Lefty Rosenthal, the inspirations behind Hyman Roth from The Godfather Part II and Ace Rothstein from Casino, respectively. Goodman was later elected mayor of Las Vegas.
Crime boss Soapy Smith, who in the 1800's started his empire by running a scam "golden ticket lottery" selling bars of soap.
For more than 30 years, Vincent Gigante disguised himself as a mentally-challenged homeless person whenever he was in public. This helped Gigante cover up the fact that he was the boss of the Genovese crime family.
Boston crime boss Whitey Bulger befriended a detective by telling him he would make sure an associate of his didn't threaten him anymore. In truth, the associate had been dead since before their conversation and several weeks later, Bulger told the detective it was taken care of.
Al Capone's oldest brother Vincenzo Capone became a Prohibition agent before Al was the crime boss of the Chicago Outfit.
The first female crime boss in the US had a gang of kids to do her bidding

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Tony Soprano, from The Sopranos, is loosely based on a real life organized crime boss named Vincent Palermo who later became a government witness

Grandson of late Gambino crime boss John Gotti, John Gotti III, is an MMA fighter. - source

Carlo Gambino, boss of the Gambino crime family. In 1974, Gambino was disrespected by a lower-ranking member of the Cosa Nostra while in a New York restaurant. He kept calm and did not retaliate. The instigator was found, not long after, encased in the cement floor of a Brooklyn social club. - source

Soapy Smith was was a con artist, saloon and gambling house proprietor, gangster, and crime boss of the 19th-century Old West. His most famous scam, the soap with a prize inside racket, presented him with the sobriquet of "Soapy", which remained with him until the day he died (in a shootout).

In 1876, James "Big Jim" Kennally, an Irish crime boss, attempted to steal Abraham Lincoln's corpse and have a ransom paid to him in exchange for the body. The ransom consisted in a full pardon for Benjamin Boyd, his friend serving a 10 year sentence, and $200,000 ($4,387,689 in 2015). - source

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About David "Blackie" Steece AKA Anthony Giordano Jr. Son of mafia boss Anthony Giordano Sr. Who grew up in the New Orleans crime family, became a US Marine and then a cop.

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Actor Lawrence Tierney, famous for his portrayal of crime boss Joe Cabot in Reservoir Dogs, was a nightmare to work with. He almost got into a fist fight with Quentin Tarantino for showing up drunk and even threatened Jerry on the set of Seinfeld when he was caught stealing a knife.

Dana White was run out of Boston by Irish-American crime boss Whitey Bulger over $2,500. He took a flight to Las Vegas where he later convinced Lorenzo Fertitta to purchase the UFC.

Former Ohio State University Defensive End Joey Bosa's Great-Grandfather, Tony Accardo, was a Crime Boss in the Chicago Outfit During a Criminal Career that Spanned Eight Decades. He went from Small Time Hoodlum to a Made Man Who Saved Al Capone's Life.

There exists a movie where Bill Murray portrays a crime boss trying to put a freak performer with wings on her back (Megan Fox) on display for paying customers and the only person that can stop him is a jazz musician addicted to heroin (Mickey Rourke)

Massachusetts' longest standing senate president, Billy Bulger, was forced to resign as president of the University of Massachusetts after he refused to testify in a 2003 Congressional hearing about communications he had had with his then-fugitive brother, crime boss "Whitey" Bulger

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In 1978 mob boss Tony Accardo had his house burgled. Shortly afterwards, the three suspected thieves and four partners in crime were found strangled and with cut throats. However, the surviving assasins were convicted and given long jail terms in 2002.

Chicago’s original crime boss in the 1800s was Michael Cassius McDonald. During a 50-year career in the underworld, journalists, gangsters, mayors and even one president of the United States took orders from him

Jan Plas was the founder of Dutch kickboxing, a style of fighting that has been very successful in modern day MMA. He was also heavily involved in organized crime and served as the bodyguard to a mob boss.

Vincent "Chin" Gigante, the boss of the Genovese Crime Family, successfully feigned insanity for over 30 years, wandering the streets of New York City in a bathroom while muttering incoherently, to avoid investigation and prosecution by the FBI.

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