10 Most Notorious Criminals Who Shook the Big Apple to Its Core!

In the pulsating heart of the “Big Apple,” where dreams soar as high as skyscrapers, lies a shadowy narrative woven with tales of the infamous.

New York City, a melting pot of ambitions, has also been a stage for some of the most chilling and cunning criminals in history.

A city that vibrates with life, yet harbors dark secrets in its alleyways and neon-lit streets.

Brace yourself for an enthralling descent into the hidden depths of New York City, a journey that pierces through the facade of its dazzling skyline to reveal a world starkly different.

1. The Dapper Don: John Gotti

John Gotti, also known as The Dapper Don, was one of the most infamous mobsters who shook New York City to its core. Gotti rose to prominence as the head of the Gambino crime family in the 1980s.

John Gotti

Becoming a part of the Gambino family wasn’t an easy task. Gotti had to enter a criminal career filled with notorious acts, such as taking part in the 1978 Lufthansa Heist and ordering brazen murders in public places.

He was no stranger to criminal charges, facing several throughout his life. However, his luck in dodging justice earned him the nickname “The Teflon Don.”

Gotti’s notoriety grew, and eventually, he became the most powerful man in New York’s criminal underworld.

2. Lizzie Halliday

Lizzie Halliday was born Eliza Margaret McNally, an Irish-American who became a serial killer in upstate New York during the 1890s.

Lizzie Halliday

Her crimes were so horrifying that she was dubbed the “Worst Woman on Earth.” In what can only be described as a chillingly gruesome spree.

Lizzie Halliday was responsible for the deaths of at least four people. Her crimes caught international attention, and in 1894, she became the first woman sentenced to death by the electric chair.

Some people even accused her of being Jack the Ripper. This was, of course, unproven, but it does speak volumes about the fear and notoriety she was able to generate.

3. Charles ‘Lucky’ Luciano

Charles ‘Lucky’ Luciano (born Salvatore Lucania) was a key figure in the development of modern organized crime. Lucky Luciano was born in Sicily in 1897 and moved to the United States with his family in 1906.

Charles ‘Lucky’ Luciano
Remo Nassi, Public domain, via Wikimedia Commons

While serving his time in prison, he struck a deal with the U.S. government to provide intelligence on the activities of other organized crime groups during World War II, which eventually led to a reduction in his sentence.

In 1946, Luciano was released from prison and deported back to Italy. However, that didn’t put an end to his involvement in organized crime.

He continued operating from abroad, expanding his businesses to include the illegal narcotics trade. Unfortunately for Luciano, his luck eventually ran out, and he passed away in 1962 due to a heart attack.

4. Joe Rifkin

Joel Rifkin was a notorious serial killer who terrorized New York City during the early 1990s. His gruesome crimes involved the murder of 17 women, most of whom were sex workers.

Rifkin’s murders occurred between 1989 and 1993 and took the lives of various women, including Yun Lee and several unidentified victims.

Rifkin dumped the bodies of some of his victims in bodies of water such as the East River, sometimes placing them inside 55-gallon oil drums to hide evidence.

It wasn’t until June 28, 1993, that Rifkin was finally apprehended. After his arrest, he would go on to confess to the 17 murders he committed, receiving a combined sentence of 203 years in prison.

5. Kendal Francois

Kendall Francois was a serial killer in Poughkeepsie, New York. Born on July 26, 1971, he was convicted of killing eight women from 1996 to 1998.

His initial encounter with the victim often took place at local motels, such as the Valley Rest Motel on October 24, 1996, with his first victim, 30-year-old Wendy Meyers.

He stored the remains of his victims in his house. The discovery of the bodies in his home led to his arrest in September 1998. Following his arrest, he confessed to the murders.

In 2000, he was sentenced to life in prison without the possibility of parole. Kendall Francois died in prison on September 11, 2014, from apparent natural causes.

6. James Coonan

James Coonan, born on December 21, 1946, also known as “Jimmy,” was the leader of the infamous Westies Gang that wreaked havoc on the Hell’s Kitchen area of Manhattan during the 1970s and 1980s.

Being the son of an accountant with ties to mobsters, Jimmy grew up exposed to a criminal environment.

The Westies eventually caught the attention of powerful mobsters like the Gambino crime family, which led to an alliance of sorts.

In 1988, Coonan, his wife Edna, and several other gang members were finally convicted under the Racketeer Influenced and Corrupt Organizations (RICO) Act.

7. Paul Kelly

Paolo Antonio Vaccarelli, more commonly known as Paul Kelly, was born in Sicily, Italy, on December 23, 1876.

Paul Kelly

Vaccarelli immigrated to the United States, where he eventually became New York’s notable figure in the criminal underworld.

Having successfully transformed his boxing prize money into a flourishing brothel business, Kelly decided to establish the Five Points Gang.

As a cunning leader, Kelly realized the power of political connections and allied himself with Tammany Hall politician “Big” Tim Sullivan.

Under Kelly’s rule, the Five Points Gang gained notoriety for their criminal activities, which included theft, extortion, and prostitution.

8. Robert Schulman

Robert Yale Shulman was an American serial killer who operated between 1991 and 1996. Born on March 28, 1954, in Hicksville, New York, Shulman worked as a postal worker on Long Island.

His criminal activities came to light when he was apprehended on April 6, 1996, and he was later convicted of murdering five women.

Between 1991 and 1996, Schulman was responsible for the brutal slayings of five women. His modus operandi involved beating and dismembering his victims.

Shulman was initially sentenced to death in 1999 for a murder committed after New York State reinstated the death penalty in 1995, but his sentence was commuted to life imprisonment.

9. Joseph G. Christopher

Joseph G. Christopher nicknamed the .22-Caliber Killer, was a notorious serial killer who carried out a series of murders in the early 1980s in New York.

His murder spree began on September 22, 1980, using a sawed-off Ruger 10/22 semi-automatic rifle concealed in a brown paper bag.

Christopher mainly targeted black men, which led investigators to believe that he was a racially motivated killer. Within just 36 hours, he managed to brutally kill three black men and one boy.

Joseph Christopher was apprehended and on March 1st, 1993, he died behind bars from a form of male breast cancer at the young age of 37.

10. Monk Eastman

Monk Eastman, born Edward Eastman, was a notorious gangster who founded and led the Eastman Gang in New York City during the late 19th and early 20th century.

Monk Eastman

Also known by aliases such as Joseph Morris, Joe Marvin, William Delaney, and Edward Delaney, he was a force to be reckoned with in the world of crime.

Monk Eastman’s criminal career had a unique twist when he served in the military during World War I.

After being wounded and recovering in a field hospital, he learned that his infantry division was preparing to breach the Hindenburg Line, Germany’s last line of defense.

Despite his notorious past, Eastman contributed to the war effort and displayed a different side of himself.

My Thoughts on 10 Most Notorious Criminals Who Shook the Big Apple

The stories of these notorious figures from New York’s criminal history highlight the complex interplay of individual actions, societal influences, and law enforcement challenges.

Their varied and often violent paths reflect the darker aspects of human nature and underscore the enduring impact of crime on society.

While their deeds were undoubtedly harmful and feared, they also serve as stark reminders of the potential consequences of unchecked criminality and the importance of diligent and effective law enforcement in maintaining social order.

These individuals, notorious in their times, now stand as cautionary tales in the annals of crime history.

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