Category: Famous Gangsters

Isiah Rynders – The most powerful Irish mob boss in New York history

Right from the 19th century onwards, New York City had been better represented by the Irish mafia gangs. Some of the Irish mob bosses included John Morrissey, Mickey Spillane, Jimmy Coonan, etc. But, it was Captain Isaiah Rynders, who is considered to be the very first mob boss of Irish origin in the mafia history of New York City.

His early life

It was on 3rd January that he was born to Irish protestant mother and German/American father. Initially, he was well known as knife/pistol fighter and professional gambler on River Mississippi region. It was during the mid-1830s that he latched on to Tammany Hall and climbed his way up the ladder. His specialty is regarded to be having Five Points Street Mobsters to be organized on Election Day and to assure the Poor Irish of offering voting rights.

Rise to fame

He earned immense wealth and owned grocery stores in huge numbers and numerous dive saloons. He also established the Empire Club in 1843. Also, he organized street gangs like Plug Uglies, Roach Guards and Dead Rabbit. His best men comprised of Country McCleester, Paudeen McLaughlin, Dirty Face Jack, Lew Baker, Jim Turner and John Morrissey. Such was the influence of Rynders that the intense prodding of voters by his men led to Franklin Pierce’s presidential election in 1852 and of James Buchanan, 1856. With Buchanan being elected as President, he had Rynders appointed as U. S. Marshall for New York’s Southern District.

Criminal activities and his downfall

He was responsible single handedly for Astor Theatre Riots in 1849. His downfall is said to have started as he abandoned Tammany Hall inexplicably along with his Irish cohorts, to join ‘Know Nothing Party’ or opposition Native American party. His political organization got renamed to the Americus Club. Taking opportunity, John ‘Smoke’ Morrissey had seized Rynders’ place as Five Points Irish mobster commander and at the Tammany Hall.

On 4th July 1857, clearly saw the power loss of Rynders when gang riots which took place in this area as well as that of Five Points. According to New York Times, clubs, stones and brick bats were noticed flying around in each and every direction and firearms were branded wildly by men.  The same evening, Rynders was called in by the officials to stop this riot, which he did by begging the rioters to stop immediately the senseless hostilities. But his words were ignored by every party involved including the gang that he once ruled.

Charlie Workman – Dutch Schultz’s murderer

Charlie was considered to be a strong person but of silent type, who had killed over 20 people, when working for Murder Incorporated, headed by Lepke Buchalter. He was popularly called ‘The Bug’ among mafia members. However, it was his killing Dutch Schultz that he rose to fame quickly.

His early life

It was in 1908 on Manhattan’s Lower East Side that Charles was born and was among the six siblings of Anna and Samuel Workman. When in 9th grade, he quit school to roam the streets, seeking trouble. At the age of 18, he got arrested for stealing cotton threat from a Broadway parked truck. The next year, he shot a man behind his year and got arrested. His reputation was such that the victim did not testify against him before law, the reason, he got sent to Reformatory of New York. He had been to prison several times for several years for parole violations.

Life as a Mafia

He worked for Lepke as freelancer schlammer or leg breaker in 1926 and did an excellent job and got promoted to becoming killer with ‘Murder Inc.’ He had a cool demeanor and had several exceptional hits, which made him to get the nickname ‘The Bug’ given by Lepke. ‘Handsome Charlie’ was his other nickname, given opposite sex.

He got arrested few times for carrying weapons in 1932 and for docking off-duty police in 1933. His specialty always remained killing. After a hit, he enjoyed taking all the valuables found with the victim and kept it to himself, thereby earning bonus in thousands of dollars.

Murdering Schultz

He was decided to be the perfect candidate for killing Dutch Schultz in 1935, when the latter did not heed to the Commission with regards to killing of Thomas Dewey, the Special Prosecutor. It was Workman who had pierced Schultz on 23rd October 1935. But he found that police officials had turned up at the sight immediately after the killing instead of a getaway car, especially after such an important hit. He discovered from the papers that Weiss was the shooter.

He was sent to meet Lucky Luciano at Miami. But he got arrested on charges of vagrancy in 1940. In the meantime, Abe Relese had spilled out to Dewey that Workman was behind Schultz’s murder, for which the latter was tried in 1941, and plead ‘no defense’ and sentenced to life imprisonment.

Allie Tannenbaum – The man responsible for Lepke’s Electric chair execution

Allie Tannenbaum was a strikingly handsome person of 14 pounds and was rail thin in structure. It was at Catskill hotel of his father that he started to work and went on to become the most accomplished killer of Murder Incorporated. It was with his help that Louis Buchalter, his boss was executed by the law.

His early life

It was in Nanticoke, Pennsylvania, on 17th January 1906, he was born. His family moved to Manhattan’s Lower East Side, Orchard Street, when he was 2 years old. He loved talking a lot, the reason why he earned the nickname of ‘Tick Tock’.

Sam had accumulated sufficient money for purchasing Loch-Sheldrake Country Club, Catskills, New York. During this time, he was in high school’s third year, quite an accomplishment for a boy who comes from a place that has record of others dropping after 8th grades and engaged in legal and illegal work. He was engaged by this father to do work at the hotel to do the menial work to groom him to become a successful businessman.

His beginning as a mafia

It is here that he came across Jewish gangsters who often frequented the club. Louis Lepke, Jacob Shapiro and Harry Greenberg were among them. Allie also had befriended Lepke’s bagman Shimmy Salles, Curly Holtz as well as Lepke himself. He got invited to their parties. However, for the work performed for his father at the hotel, he was not given a single dime. He had noticed the Jewish gangsters to have sufficient money with them, which lured him to the mafia world.

He started to work for Lepke upon the behest of Big Harry Schacter for $35/week, performing activities like throwing stink bombs, strikebreaking and slugging. Later, he graduated to duties such as schlammings. His pay increased with work production and got involved in about 6 murders. He became Lepke’s valuable asset. Killing Harry Greenberg in 1939 was his biggest achievement, as it was Southern California’s first ‘mob killing’.

In 1940, he got arrested along with Workman at the latter’s place. Although he refused to speak the first three days, upon being threatened of being executed, he lived up to his nick name spilled out everything, the murders and the Lepke mafia connection. He testified against Lepke on a murder charge, which led to the latter’s being sentenced to death by the electric chair.

The remaining part of his life went into hiding, since he emerged only to testify against his other mafia members and disappear back. At the age of 70, he died due to natural causes.

Abe Wagner – The chicken hearted mobster

Abe was regarded to be a bootlegger and thug operating on the Lower East side of Manhattan and was of Jewish origin. He compared himself to that of Dropper even had roughened up Joe Masseria’s son to show him what he is capable of. Fortunately for Wagner, before taking revenue for insult caused to his son, Masseria got gunned down.

Mafia activities

With Allie, his brother Wagner had been making a decent living in bootlegging business on Lower East Side. On 20th February 1932, when he was riding his new car, he got attacked by some shooters and managed to escape in the crowd. Although he claimed to be a tough soul, his activities proved him not to be one. After the attack, he tried to be in peace with the enemies. To achieve this, he had sent his brother and an associate to meet the Mazza and hand over to them a huge amount for leaving him off. But in the process, Albie was shot dead and a message was left to Wagner that the Mazza meant business and his death.

He was prodded by his mother to seek refuge elsewhere from the Mazza gang, since she did not want similar fate for the other son. He took his wife and left town. However, in New Jersey’s Hopewell region, the Lindberg baby got abducted, which made Wagner to come under suspicion by the law enforcement officials.

More trouble for Wagner

At the same time, the Mazza Gang having aligned with the likes of Lucky Luciano searched for Wagner throughout the country. To check out on his mom, he sneaked back into New York.  On understanding that his presence came to light by the gang, he again ran with his wife and had his identity changed to Abe Loeb taking the profession of a fruit seller. But in weeks, Wagner was noticed by Luciano’s men. Two mobsters from Luciano’s Murder Incorporated were sent to kill Wagner, who was quite knowledgeable about the place where the latter hid, as it once had been their hideout too.

With Al Gordon, the new partner, Wagner on 25th July 1932 was followed by the two mobsters and killed both. Wagner succumbed to injuries, was taken to the nearby Ancker Hospital, where he died hours later, whose real identity was confirmed by his mother.

Philip Rusty Rastelli – The man who controlled the Bonnano family from the prison

The early boss of the Bonanno Mafia family was Phillip Rastelli during the 1970s. He was the successor to Joseph Bonanno.  By occupation, he was a radio dispatcher working for a taxi firm, but got convicted and sentenced to 10 year imprisonment for antitrust violations. It is from prison that he directed the family’s operations, but his influence not being strong enough from behind the prisons, waned slowly.

His life as a mafia

On 31st January 1918, Rastelli was born in Maspeth, Queens and was among the five siblings Marinello, Carmine, Grace, Justina and Augustus. He got involved heavily in extortion, drug trafficking and loansharking before he became the member of the Bonanno Mafia family. He was close to Carmine Galante, Joseph Massino, Joseph Bonnano and Dominick Napolitano.

Along with an associate on 3rd December 1953 he had shot William Russo, but the latter survived, which made Raselli to go into hiding. On 13th December 1954, he got indicted on bribing charges. In 1962, Connie got killed after she had become Federal informer, after which her body never was found.

Rise in the family

The Commission for restoring the Bonanno family in 1969 had appointed 3-Man panel comprising of Natale Evola, Joseph DiFilippi and Rastelli to run the family. On 21st July 1971, he again got indicted on loansharking charges in the Riverhead neighborhood of New York. Evola died on 28th August 1973, following which the Bonanno family’s acting boss was Rastelli. He was made official boss by the Commission at a meeting held at Manhattan’s Americana Hotel on 23rd February 1974. However, the family’s real power was transferred to Carmine Galante, the underboss and rival to Rastelli.

On 6th March 1975, he was convicted for anti-trust violations and extortion and imprisoned in the federal prison of Lewisburg, Pennsylvania. It is from here that he had ordered the murder of Galante in 1979 on the permission of the Commission, who also felt Galante was not suitable for their business. This way, he went on to become the family’s undisputed boss, although the acting boss until he was released from prison was Salvatore Ferrugia.

Later life of Rastelli

An internal war started within the Bonanno family in 1981, on Rastelli’s continuation as its boss. Several people were murdered which also included Alphonse Indelicato, the opposition Bonanno caporegime leader. Joseph Pistone, the FBI undercover remained witness to this power struggle.

Rastelli died due to liver cancer on 24th July 1991.

Owney Maddon – The English-American boss of Gophers gang

Owner Maddon was considered to be an anomaly among the underworld of New York City. The reason for this is not because, of his not being of Italian or Jewish origin, but being British.  He was popularly called in his circles as ‘The Killer’. He was the son of an Irish dockworker, bred and born as well as dedicated towards his homeland – England. Although he was regarded to be a notorious American mafia for about six decades, Maddon never thought of leaving his English passport until he got threatened with the consequence of deportation.

His early life

It was on 18th December 1891 at 25, Somerset Street, Leeds, England that Madden was born. His father to seek work had shifted base to Liverpool. At the age of 12 in 1903, his father expired, compelling his mother to relocate to the United States and to settle on Manhattan’s west side that was popularly known as ‘Hells Kitchen’, then a treacherous neighborhood.

His life as a mafia

It is here that he came across a rough gang called the Gophers and soon indulged in several types of criminal activities like labor racket beatings, muggings and robberies, in which he had become quite proficient. He also was an expert to use different types of weapons like the brass knuckles and slingshot. However, the lead pipe that was wrapped in newspaper which was his favor tie weapon. The ‘insurance business’ was his income source. The local merchants were sold with ‘bomb insurance’ by Madden to protect themselves from being bombed by Madden himself. He had been arrested about 44 times, as the Gopher’s member, however, was able to stay clear from being imprisoned.

He was given the nickname since he had killed an unarmed Italian for no reason and to his credit had committed 5 other murders by the age of 23. On 6th November 1912, he was shot by 11 Hudson Dusters, rivals of Gophers that he survived. He had a gang member killed who had planned to usurp his position, which led to his being sentenced for 10 to 20 years. After being released early, he got into bootlegging business, moving up in class, he got compared to mobsters like Frank Castello, Lucky Luciano, Louis Lepke, Meyer Lansky and Bugsy Siegel. In 1932, he retired the life of a mobster and relocated to Arkansas, where he died at the age of 74 due to emphysema.

American Mobster – Nathan Kaplan – Kid Dropper

Nathan Kaplan: Paul Kelly’s Jewish successor
It was in 1891 at Manhattan’s Lower East Side that Nathan Kaplan was given birth. At a very young age, he hit the streets to get engaged in petty crimes, swindlers like the ‘dropper’ scheme. He would simply drop a wallet full of fake money and have an innocent, but greedy person to have it against half of the money as reward, which did click huge for Kaplan. It is for this reason, he had earned the name ‘Kid Dropper’.

His life as a mafia

His expertise led him to join the Five Point Gang of Paolo Vacarelli (Paul Kelly), something unusual for Dropper, since he was of Jewish origin, while the gang was of Italian descent. But he got arrested in 1911 for robbery, sent for seven year at Sing Sing Prison. Kelly’s gang had disbanded by the time of his release in 1917. He presumed himself to be the successor to Kelly and started to take over the latter’s labor racket business.

His rise as a mobster

He preferred to wear slovenly attire like dressing as a bum until his being imprisoned. But after becoming the boss of the gang, he dressed accordingly and started to wear loud checkered suits, shirts, ties having loud colors, pointed shoes, outlandish designs, straw hat and the like. He gathered low level gangsters, which he called ‘Rough Jack Dropper Riders’. But soon he had come cross roads with Joseph Weyler, a Kelly gangster of Spanish origin, who always wanted to control over Kelly’s rackets. But with his death, Dropper regained charge of the gang and the racketeering efforts.

He was held responsible for over 20 murders between 1920 & 1923. However, he had again to face competition from Jacob Orgen or Little Augie as he was nicknamed,  who was eager to control all the illegal activities of Doppler and had engaged the best killers in his gang like Gurrah Shapiro, Louis Buchalter and Jack Diamond. Manhattan from 1922 to 1923 was turning into a shooting arena for both the parties involved, resulting in 23 murders including that  of an innocent man.

He was charged for having concealed weapons and got arrested in 1923, but later he got released outside of Essex Market Court. He had provided with tight police security because of rumors of his being murdered, when released from Court. But, Louis Kushner, an aide of Little Augie shot him in the head twice and killed him.







John Allen – New York City’s most wicked mobster and pimp

John Allen is regarded to be a murderer, pimp, drunkard and con artist, who are known in American mafia history as one who had run the most obscene of all dance halls in New York. Due to his transgressions being huge, he had been nicknamed as “New York City’s Wickedest Man”.

His early life

It was in upstate New York in 1823 that he was born and was among the 8 siblings of his parents and the youngest of them all. His father had been a well known Presbyterian minister, while one brother had become Baptist minister, while two others had become Presbyterian ministers. The other brothers had ran away to the city of New York to become crooks,  confidence men and burglars, owning different bawdy bars located in Manhattan’s Lower East Side.

His entering into the crime world

His father wanted Allen to select the righteous path by sending him to Union Theological Seminary and not the path chosen by his other brothers. For few months, Allen studied religion, however, was more inclined towards leading the kind of life his other brothers were leading at New York. It is his brothers, who had introduced him to the world of crime making him proficient in the trade.

He came across Little Suzie, a well known criminal and married her in 1855. Her specialty was said to be rolling drunks, seduce clients and have knockout drops placed in their drinks. She carried her activities in 4th ward, waterfront district. Allen too got hold of a job for the waterfront crimp, where his work was to lure sailors to the establishment and drugging them, robbed of their money and valuables.

After the death of his boss, he was employed by Jane the Grabber of Hester Jane Haskins, which runs numerous ill reputed houses. His job was to lure young girls to provide them with good paying jobs, get them drugged and work at Jane’s brothels.

He had the opened up a Dance Hall in 1858 that went on to become the most shameless establishments of the city. It is this that had prompted Oliver Dyer a journalist to state in an article for Packard’s Monthly as John Allen being the city’s wickedest man, which was gracefully accepted by Allen and had it proudly displayed on his business card and had become the city’s richest pimp. However, his plan to introduce semi-religious sentiments within the dance hall to earn more money simply backfired.

Jack Diamond – The invincible Gangster

Jack Diamond had a nickname called ‘Legs’. He had been shot several times and injured badly. It was on 10th July 1897 that he was born to Irish parents, who belonged to Kilrush, County Clare, Ireland. Most of his early years were spent in Philadelphia. At the age of 13, his mother died due to viral infection, after which along his brother, he had joined ‘The Broiler Gang’, a local group of toughs. On charges of mayhem and robberies, he had been arrested dozen times and had to spend few months at a juvenile reformatory. He was drafted to the army, which did not suit him and left within a year and absconded. Being caught, he got sentenced to 3-5 years of imprisonment at Federal Penitentiary, Fort Leavenworth, Kansas.

His career as a mafia

In 1921, he got released from prison after which he moved to New York to make some fortune. Along with his brother Eddie, he got relocated to Lower East Side of Manhattan and came across Lucky Luciano, for whom he performed numerous odd jobs, which included bootlegging. He married Florence Williams, but it lasted just few months. He was introduced to Arnold Rothstein by Luciano after his fortunes changed. Rothstein was a financial wizard and notorious gambler.

His rise to popularity as a mafia

He worked as Rothstein’s bodyguard and was made his partner to carry out heroin business. Once he had accumulated sufficient money, he along with his brother had ventured on their own. They hijacked other mobsters’ bootlegging trucks like Big Bill Dwyer and Owney Madden, which proved to be a bad idea making him target of all mafias.

His later life

He escaped being ambushed in October 1924. Soon, he befriended Little Augie and became his chief bodyguard, for which he got as a reward share of Augie’s narcotics and bootlegging business. But with the gunning down of Owen, even Diamond was injured. On his release from hospital, he befriended Shapiro and Lepke and got a share of narcotics and bootlegging business from them.

He was noticed regularly at few clubs and as well as his pictures in leading newspapers, which portrayed him as handsome man-about-town and not a gangster. He then owned clubs. However, 13th July 1929, his fortunes turned down. In December 1931, he got shot at Kenmore Hotel, Albany, apparently by two unidentified gunmen, putting an end to the otherwise, ‘invincible man’.

Dutch Schultz – The lunatic mob boss

One certified lunatic mob boss that existed in the opening of the 20th century was Dutch Schultz. He was born in the Bronx in 1902 to Jewish/German parents and his original name was Arthur Flegenheimer. At a very early age, his father had abandoned the family and this made Arthur to take up variety of jobs, which included working at Schultz Trucking Company. Although he was into legitimate work, still he was influenced by the crooks, who were into bootlegging during the Prohibition time.

His life as a mafia

As he got caught by the police  officials for the initial time, he stated his name to be ‘Dutch Schulz’ that was the boss’ son’s name, to which he later confessed that this name appeared in the headlines much better than that of his own name ‘Arthur Flegenheimer’.

Quitting this job, he planned to join numbers racket at Harlem, where about $35,000 was bet in a day by the locals. He established a gang, including Otto Berman alias Abbadabba – a mathematical genius, Lulu Rosenkrantz and Bo Weinberg. The black gangsters were invited by the crew to a meeting as the former had control of the Harlem numbers racket and became a partner.

His rise to fame

Schultz was eager to do something else besides Harlem numbers. He took the help of Abbadabba for rigging the numbers game for achieving the goal, the money from which would be diverted to new rackets. He became popular as a mobster who could bear insult of his girlfriend, even spitting on his face, but not anyone stealing from his account. If done, then that person is sure to be dead.

He shot Vincent Cole and Jack Diamonds, which propelled him into big time, after which he had become equal in position to mafia gangsters like Louie Lepke, Lucky Luciano, Meyer Lansky, Joe Doto and Albert Anastasia. Although he raked in millions of dollars, he spent very less on his suit and shirt.

His later life

His erratic ways only made his crew to become weary of him. An instance was his conversion to Catholicism for evading tax in Malone, New York, which helped him to get acquitted. But it was after his murdering Thomas E. Dewey, the special prosecutor of New York City, going against the syndicate that made him unpopular with them. A conspiracy to kill him was executed on 23rd October 1935, in which he was killed.

Dominick Napolitano – The successful crew leader and right hand man of Philip Rastelli

Dominick Napolitano had a nickname called Sonny Black. He was born on 16th June 1930 in Williamsburg, Brooklyn. He started his life as petty thief. Although, his family belonged to Naples, Italy, he had a blond hair during birth, which he dyed black once he grew up, thereby earning that nickname.

His personal life

He is regarded to be an avid enthusiast for pigeons and had them kept at the apartment building’s rooftop. The pigeons were said to be prized coming from pedigree bloodlines from Russia, Germany and France. He often used to visit his coop, which according him made him to feel peace of mind and to help think better. He befriended Brasco, who actually was a FBI undercover and explained him the activities and functions of the Mafioso.

As a mafia

He had controlled parts of Florida and Pasco County after getting the approval of Santo Trafficante Jr. and the Trafficante Mafia Family. Orlando at that point of time was considered to be a developing gambling district, which prompted Napolitano to start a bookmaking operation here. He is known to have owned Motion Lounge – a social club and apartment building in New York. His lounge had become his headquarters for his crew to get involved in numerous illegal activities such as robbery, burglary, loansharking, bank robbery, bookmaking, and hijacking, drug trafficking, casino operations, extortion, etc. His crew was regarded to be the leading in the family and a successful one.

After the murder of Carmine Galante in 1979, he got promoted to the rank of a capo, while Michael Sabella, his mentor was demoted, on whose place he came. He took over the crew of Sabella and had become a confidante and close aid of Phillip Rastelli, the Bonanno Mafia Family’s boss. But the Bonanno family got split into two groups, with one behind Rastelli and the other by Alphonse Indelicto, with both fighting for the top position. It was the responsibility Napolitano and Joseph Massino to have the power struggle to be ended and their task was cut to killing three capos namely Alphonse Indelicato, Philip Giaccone and Dominick Trinchera.

According to Pistone, Dominick was much more disciplined and observant and also had watchful eye. When it came for personal loyalty to sidewalk soldiers, he simply had a wonderful reputation.

On 17th August 1981, he was shot to death for allowing FBI agent to be in his crew.

Boss Tweed – New York’s elected crooked politician and mobster

William Tweed is regarded to be an outlandish crooked politician, who is known to have proved to be devilish to the city of New York, upon his being elected in office. He was popularly called by his associates as the ‘Boss’. By 1870, he had stolen plenty of cash from the coffers of the city of New York, using which he had become the city’s 3rd largest land owner.

His early life

It was on 3rd April 1823 at Lower East Side, Manhattan’s Cherry Street that William Tweed was born. He was the 3rd generation Irish-Scottish descendant. His father worked as chair maker. When young Tweed followed his father’s footsteps, however, the streets did lure him a lot. He went on to join ‘Cherry Street Gang’, a juvenile delinquent crew, who were said to have created problems for the local merchants. They stole wares and had them sold on the black market. He became the gang’s boss and joined numerous volunteer fire companies that were regarded to be the perfect platform for those having political aspirations. He also assisted in establishing the No. 6 American Fire Engine Co., called popularly the Big Six, where he befriended people from all communities and ancestries, those who could help him propel to public services with a motto to steal big.

His rise to fame

He got elected as alderman in 1851.  Although having unlimited power, he had brokered a deal for purchasing land for new potters field with asking price being $30,000 and Tweed paying $103,450 for the land from the city’s money. The excess money had been distributed among him and other corrupt elected civic officials.

He got elected to elections’ city board in 1855 that saw more cash flow. For making profits, he sold teacher’s jobs and city textbooks. He got appointed as Supervisor in the City Country Board that helped him to thieve much more, by creating a Tweed Ring, thereby controlling every work permit and job of the city. Every merchant, artisan and contractor had to pay up in plenty to do business here. He had amassed immense wealth by 1865. He had a great reputation for eating and stood 5” 11” tall and weighed 320 pounds and flouted tremendous wealth. Over $200 million were stolen from the treasury between 1865 and 1871.

It was in late 1869 that problem arose for Tweed, when a cartoon was published in Harper’s Weekly prompting Samuel J. Tilden, the future Presidential candidate to investigate the financial documents, leading to his arrest. Being convicted in over 200 counts, he was sentenced to imprisonment, where he died on 12th April 1878.