When we think of gangs, we usually think of a group that is threatening people’s peace. However, there are areas where gangsters have glorified gang activities and even made the gang groups into something much bigger than just mere gangs. The gangs would operate as legitimate businesses and even involve themselves in political affairs. Here are the most infamous gangs in New York City.
The Forty Thieves
The Forty Thieves, one of Gotham’s oldest documented criminal organizations, operated in Manhattan’s Five Points district during the 1820s and 1850s. This gang of Irish thugs, pickpockets, and ne’er-do-wells first banded together in Rosanna Peers’ grocery store and dive bar.
What started as a ragtag bunch of minor criminals under the leadership of Edward Coleman, evolved into a feared street gang with its own set of rules and organizational structure. The Forty Thieves had daily quotas that compelled them to steal a particular number of things or suffer expulsion. Furthermore, the gang established a franchise in the form of the Forty Little Thieves, a group of young trainee pickpockets and lookouts.
The Bowery Boys
The Bowery Boys were a band of lower Manhattan toughs that struggled with the Irish Five Points gangs during the 1840s, 1850s, and 1860s. They were one of New York’s most notorious gangs. Unlike some of their criminal rivals, the majority of the Bowery Boys dressed elegantly and worked as mechanics, printers, and other apprentice tradesmen. When they were not on the job, these youthful hoodlums hung out in the Bowery’s saloons and back alleys, fighting in brutal turf combat with rival gangs like the Dead Rabbits.
The Bowery Boys frequently behaved as a political club rather than a gang, and many of their fights were with followers of opposing candidates. The gang would sometimes station members at voting sites or polling stations to frighten voters into supporting a specific candidate. In exchange, once the politician was in office, the gang’s home district would receive money and favorable treatment.
The Dead Rabbits
This gang of Irish immigrants was one of the most dreaded to emerge from Five Points, so named because it was located at the crossroads of five crooked, small downtown streets. Five Points has been one of the city’s most notorious and dangerous neighborhoods for more than 6 decades.
Throughout the 1850s, the Dead Rabbits excelled at thievery, pick-pocketing, and fighting, especially against their sworn adversaries, the Bowery Boys. The organization was largely made up of young guys, but it was not unheard of for women to participate in the violence.
One of the most dreaded Dead Rabbits, according to folklore, was Hell-Cat Maggie, a lady who wore brass fingernails in combat and filed her teeth to points. While the Rabbits were generally engaged in minor criminality, they are famous for the events of July 4th, 1857, when one of their street fights with the Bowery Boys erupted into a deadly riot that killed more than 10 people.
The Dead Rabbits were said to be an offshoot of another gang known as the Roach Guards, but some historians believe that the 2 were the same thing. According to one common interpretation, the term dead rabbit was just a derogatory epithet that the Bowery Boys and the New York newspapers used to describe members of the Roach Guards and other Five Points, gangs.
The Daybreak Boys
New York’s 19th-century gang activity extended beyond the rough and tumble streets of Manhattan and into the waters of the East River. The Daybreak Boys were a violent group of river pirates that preyed on the city’s thriving shipping industry in the 1840s and early 1850s. The Daybreakers, whose leaders were called Cow-legged Sam McCarthy and Slobbery Jim, tended to strike in the early hours of the morning, as their name indicated.
These young crooks would sail discreetly alongside anchored commercial vessels in little rowboats. They would get aboard and take as much cargo or goods as they could before returning to their dinghies and fleeing to a rendezvous spot near a gin mill in the Fourth Ward.
Prospective members were allegedly expected to have murdered at least once before joining the organization, and the Daybreak Boys were allegedly accountable for over 24 killings. It was not uncommon for an unlucky watchman to end up with a slit throat or a shattered skull during one of their thefts. The gang allegedly disbanded in the 1850s as a result of a police crackdown, but not before claiming thousands of dollars in spoils.
The Whyos
From the 1860s through the 1890s, the Whyos were one of the most powerful New York street gangs, established from the leftovers of many defunct Five Points enterprises. The gang started as a loose collection of petty thugs, pickpockets, and murderers, but by the 1880s, they had progressed to higher-level crimes like forgery, prostitution, and racketeering, dealing with dishonest and fraudulent business dealings. As the gang’s hold on Manhattan became tighter, several of them started respectable side businesses like saloons and casinos.
The Whyos may have pretended to be good citizens, but they were infamous for being difficult clients. A hood named “Dandy” Johnny Dolan was said to be carrying a copper eye gouger and wearing shoes with axe blades. The authorities once captured Piker Ryan, another Whyo, with a full price list of all the heinous crimes that one hired him to commit. A simple punch to the face cost $2, chewing off an ear cost fifteen dollars, and a murder, defined in Ryan’s catalogue as “doing the big job,” cost more than $95.
The Five Points Gang
The remaining members of the Dead Rabbits, Whyos, and other Five Points gangs united under the banner of the Italian criminal Paul Kelly in the 1890s, becoming a renowned mob.
Kelly led an army of over 1,000 thugs in brutal turf fights with his archrivals, a Jewish gang which Monk Eastman led from his headquarters in the New Brighton Dance Hall. The two groups were constantly fighting and once engaged in a major gun battle beneath the Second Avenue elevated railway line.
When they were not engaging in Wild West-style shootouts, the Five Pointers were involved in extensive robbery and prostitution rings. They also ran respectable front enterprises and acted as go-betweens for the corrupt Tammany Hall political machine. The gang’s power faded in the 1910s, but not prior to helping groom the next generation of crime chiefs. Among others, the Five Pointers introduced Lucky Luciano, Al Capone, and Johnny Torrio to the world of organized crime.
The Eastman Gang
In the 1890s, the Eastman Gang rose to become one of New York’s most feared criminal groups. The 1,200 Eastmans, who ruled Manhattan’s Lower East Side, made a fortune through brothels, protection rackets, drug gangs, and even murder-for-hire operations. Eastman’s lads linked up with corrupt politicians to commit voter fraud. In exchange, the city’s corrupt politicians turned a blind eye to the gang’s criminal actions.
Monk Eastman, a lifelong criminal, reveled in violence and was popular for personally abusing his foes. When the authorities arrested and imprisoned him for a minor street mugging in 1904, his hands-on attitude proved to be his doom.
In the 1910s, the Eastmans divided into numerous smaller, less powerful groups after their leader was in prison. Monk Eastman later joined the military and earned a famous reputation for fighting in the WW I trenches. The former gang boss’s previous life eventually caught up with him, and the police shot him mercilessly on a city sidewalk in the early 20th century (1920).
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