5 Jaw-Dropping Tales of Notorious Mob Bosses

The mysterious world of mobsters is filled with intrigue, power, and unexpected stories. These underworld figures have inspired countless movies, books, and TV shows, but the real-life escapades of some mob bosses are stranger than fiction. Let’s unravel five such astonishing tales from the annals of mafia history:

1. A Father’s Wrath: John Gotti, one of the most formidable mob bosses, faced personal tragedy when his youngest son was tragically killed by a neighbor’s car. This accident would seal the neighbor’s fate, for he mysteriously disappeared shortly after. It’s widely believed that Gotti avenged his son’s death by having the neighbor’s body dissolved in a 55-gallon drum of acid.

2. The Invisible Boss: Despite being one of the world’s top ten most wanted criminals and holding the title of ‘boss of all bosses’ within the Italian Mafia, this mastermind has eluded authorities for over 26 years. What’s even more baffling is that there isn’t a single photograph of him from this period of evasion.

Mugshot of Messina Denaro taken after his arrest in 2023
Mugshot of Messina Denaro taken after his arrest in 2023

3. The Patriotic Mobster: During the tumultuous times of World War II, “Lucky” Luciano, from behind his prison bars, played an unexpected role. He commanded his mafia men to shield the East Coast from any foreign threats. Further showcasing his strategic prowess, Luciano persuaded his Italian mafia connections to back the Allies during their invasion of Sicily.

4. The Peculiar Act of the Oddfather: Deception and theatrics aren’t uncommon in the mob world. One particular Mafia boss took this to another level, feigning insanity for three decades. He roamed Greenwich Village, dressed in pajamas and murmuring nonsensically, all to sidestep legal prosecution. This eccentric act earned him the nickname “the Oddfather”.

5. The Devout Assassin: Loyalty to traditions can manifest in the unlikeliest of ways. “Red” Levine, reputedly Lucky Luciano’s preferred hitman, was an Orthodox Jew with a unique modus operandi. He never conducted his dark deeds from Friday evening to Saturday evening, observing the Shabbat. However, if circumstances demanded an assassination during this holy period, Levine would don a prayer shawl, offer his prayers, and then proceed with his grim task.

Five Unbelievable Stories from the Gangster Underworld

Plunging into the thrilling and often murky depths of the criminal underworld, let’s uncover five jaw-dropping tales about infamous gangsters.

John Gotti just after his arrest in 1990
John Gotti just after his arrest in 1990
Photo by Wikipedia

1. Hymie Weiss, the notorious gangster from Chicago, was known for his audacious encounters with the formidable Al Capone, earning him the unique distinction of being “the only man Al Capone feared.” Weiss’s fatalistic approach to his own life can be traced back to his terminal cancer diagnosis. Fearlessly embroiling himself in gang wars against Capone, he even assaulted Capone’s car and lodging place. However, Weiss’s brazen actions led to his demise, as he was assassinated on October 11, 1926.

2. Famously known as ‘The Teflon Don’ for his uncanny ability to evade legal charges, John Gotti was a notorious figure in the criminal world. Yet, his brutal and conspicuous methods eventually led to significant crackdowns on the Gambino crime family. In 1992, Gotti was convicted, and by the start of the new millennium, half of the made men in the Gambino family found themselves behind bars.

3. Sammy “The Bull” Gravano, once the underboss of the Gambino family and instrumental in Gotti’s downfall, now freely shares his mafia tales on a YouTube channel. Gravano, with his self-proclaimed immunity from testifying against the mob, unabashedly discusses his involvement in numerous murders. His stories, while always taken with a pinch of skepticism due to the notorious unreliability of mob members, often bear an uncanny resemblance to a Martin Scorsese script. Gravano’s exploits dwarf the characters of “Goodfellas,” affirming him as a genuine figure in the mafia world.

4. In a peculiar turn of events in 1926, acclaimed jazz pianist Fats Waller was abducted by gangsters and held for three days in Chicago. The surprising reason? To perform as the “surprise guest” at Al Capone’s birthday celebration. Waller was eventually discovered in a state of extreme fatigue and intoxication, his pockets bulging with thousands of dollars he had received as tips from Capone and other party guests.

5. In a chilling display of gangster loyalty, Frank Gusenberg, a mobster riddled with 14 bullets during the infamous St Valentine’s Day massacre, steadfastly refused to reveal his attacker. His final defiant words, “I ain’t no copper,” went down in underworld history.