Colosimo, Jim: AKA Big Jim. Born 1871 Died 1920 Founder of the Chicago Mob.
The Chicago mob was born out of the Levee one of the city’s first red light districts. Officially the area had at least 50,000 prostitutes at a time when Chicago, city wide, had 81,000 known prostitutes and 52,000 known Procurers.
During the first decade of the twentieth century, the Levee held approximately 1,020 brothels that employed about 5,000 people and produced about $60,000,000 a year in revenues. Reporter and author Jack Lait wrote: “There were no respectable enterprises... (it was) a city within a city dedicated to drinking, dancing and catering to every lechery and lust that man or woman could contrive.”
Colosimo came to grew up in the Levee. He arrived there at age 17, from Cosenza in Calabria, Italy. He shifted back and forth between an honest working man’s chores and a criminal’s world. He worked as a bootblack and burglar, a water carrier for the railroads and a pickpocket.
In 1902, while making his rounds to the brothels as a collector for the local political/ gangster bosses, Colosimo met Victoria Moresco, a fat, unattractive, middle-aged Madam who operated four second-rate brothels on Armour Avenue.
Victoria fell in love with Colosimo and Colosimo, seeing the potential in taking over Victoria’s operations, married her a week later.
By 1903, Colosimo had added at least thirty-five more brothels to his wives chain, almost all of them one and two dollar brothels although he did open two better classed operations, the Saratoga and the Victoria, named after his wife. Colosimo was making a fortune. For every two-dollar the prostitutes earned, he took $1.20 plus something off of each drink purchased. He expanded into labor racketeering, taking over several unions and skimming thousands each month from their treasury.
By 1915 he was a millionaire. He started wearing hand-tailored suits and dozens of diamonds, on his belt, his shirt studs, his rings and cufflinks and was a power almost equal to the levels political bosses, Kenna and Coughlin. Colosimo had two limousines driven by uniformed chauffeurs. He bought a mansion for his father and one for himself that he crammed with leather-bound books and imported Turkish rugs. While the up-and-coming hoods in New York styled themselves after Arnold Rothstein’s (1882-1928) demure style of clothes and speech, in Chicago a young hood fashioned himself after Colosimo in his expensive shiny clothes.
Flush with cash, Colosimo opened his own place in 1910, a gaudy café on Wabash near 22nd Street where he held court, swaggered and played the host—a role he relished. It was the gaudiest yet the most elegant place in town. It had a mahogany and glass bar, the dining room had green velvet wallpaper and trim gilded ceiling in sky blue with solid gold chandeliers over the dance hall floor which raised and lowered by a hidden hydraulic lift.
The basis for all of Colosimo’s money was a massive prostitution racket, but the ongoing problem in the Levee was that there were never enough women to meet the demand. The turnover was amazing, the women who didn’t commit suicide, stab each other, get killed by a Procurer or a customer, or overdose, usually lasted about three years. To keep the stock up, Colosimo resorted to white slavery, kidnapping young girls, dragging them into the Levee, raping them and then “turning them out” to brothels or street Procurers for a hefty price. Colosimo made at least $600,000 a year from the slave trade alone, an incredible amount of money in 1904.
The Levee’s leading white slaver was Maurice Van Bever, a vain dandy who drove about the Levee in a red carriage driven by top-hatted coachmen. Van Bever and his wife Julia ran two of their own brothels on Armour Avenue and it was natural that he should meet Colosimo. The two decided to go into the white slavery business together in 1903 and set about the business of making contact stations in New York, St. Louis and Milwaukee. Over the next six years and up until 1909, they imported no less than 600 young women for sale into the Levee and other fleshpots across the country.
It was at this point, about 1909, that Colosimo and his flashy lifestyle came to the attention of another Italian import, the Black Hand. The Black Hand was not the Mafia or even organized crime. Rather it was an ancient extortion racket run by professional criminals. Their methods were simple.
They would decide on a victim, send a long, flowery message demanding payment. When Colosimo got his letter from the Black Hand he took it seriously. In one period in Chicago, between 1895 and 1925, there were a reported 400 Itlo-Americans gunned down by the Blackhanders, hundreds if not thousands more paid off. But Colosimo was one of those who paid off, $5,000 at first. Colosimo knew what was coming next; he too had once been a Black hander. More demands would come and the price would go up with each demand. There was nothing his political contacts could do for him, even with the entire police force at their disposal. Colosimo didn’t have the stomach for a fight anymore, so he sent for his nephew in New York, Johnny Torrio. (1882-1957) In New York Torrio ran a gang called the James Street Outfit and was tied into the City’s political machine, Tammany Hall.
Torrio had entered the New York rackets under the guidance of gang leaders named Paul Kelly when Kelly’s gang was locked in a vicious gang war with a hoodlum named Monk Eastman, who was accurately known as “The Terror of the East Side”
When Monk Eastman showed up at the New York National Guard recruiting station in October 1917, the Doctors on duty were pained at the razor, knife and bullet scars on his body.
He had bullet entry wounds in his stomach, which he proudly told Doctors that he had plugged with his own fingers to stop the bleeding. His nose was broken nose, mashed flat actually, cauliflower ears although the ears were barely there, having been nearly slashed off of him in various street brawls years before, and lacerations almost covering his face and body including his ankles another that ran up to his barrel chest and crisscrossed his neck and face.
Monk Eastman (Also known as Joseph Morris, William Delaney, Edward Delaney, Joe Marvin, and Joe Marrio.) was born Edward Osterman in Brooklyn New York in 1873 (The exact date is known) to respectable Jewish immigrant parents who ran a Kosher restaurant
Eastman had an odd, considering his violent and dangerous disposition, and extreme fondness for cats and birds and eventually opened a pet shop on Broome street in Lower Manhattan. He was what one might describe as an early animal activist and grew so attached to his animal that he never sold any of them. Instead, the shop eventually became a drop off center for strays.
In about 1895, the Monk moved to lower Manhattan and managed to become a City Sheriff of New Irving Hall. Sheriffs then were more or less legally armed bouncers in bars owned by politically connected Hoods. He developed into a slovenly dresser, wearing the standard hoodlum bowler hat that was several sizes too small for his head (It was where pistols were kept) He developed a clipped, slang filled speech, to match the blackjack tucked into belt and a pair of brass knuckles on his hands. Younger hoods began to imitate his slang and sloppy clothes.
After a few years, Monk quit his position the Sheriff’s office and formed his own gang, the Eastman’s who were headquartered in a dive-saloon on Chrystie street, near the bowery. Here the gangsters stockpiled slung-shots, revolvers, blackjacks, brass knuckles, and weapons of the street.
Although he was known by a number of alias’ he was known best as Monk Eastman, and he lent this name to his gang, the Eastman’s, 1200 strong, a band of incredibly tough muggers, safe crackers, pickpockets, and second story burglars who eventually moved into the more lucrative fields of gambling, extortion and prostitution
The Eastman gang ruled the area between the Bowery and 14th Street, which was, for decades, a no-man’s land where pitched battles were fought weekly between the Eastman’s and their rivals, the Yakey Yakes, the Red Onions and Paul Kelly’s Five Pointers.
Early on, while still in his teens, the Monk worked as a bouncer in the New Irving dance hall and carried a sawn-off baseball bat with a notch for every head he cracked. It was a rough place and Monk bragged that he had once beaten up a customer for no other reason than to add a new notch and “make it an even 50”.
He looked on it as practice since the Eastman gang carried out beatings for money, $15.00 (Which was much more than it is today) for a sound beating, a beating and a stabbing went for $25 and a murder, without the beating went for a flat $100.
He had a fondness for the black jack and bragged about his skills with the weapon but was always careful to point out that he had never blackjacked a woman or, to his knowledge murdered a woman. He did however admit to beating women and blackening their eyes.
He was vicious and so active at his trade that the ambulance drivers at the Bellevue hospital to nickname the Accident and Emergency Ward the “Eastman Ward”.
At the height of it’s power, about 1890 to 1905, the Eastman gang had approximately 1200 members and a territory between Monroe Street, 14th Street, the Bowery and the East River. It’s main source of money and protection came from contracts from corrupt Democrat politicians William “Boss” Tweed and Richard Croker of the equally corrupt Tammany Hall. For a fixed flat rate and consideration in legal matters, the Eastman’s intimidated voters, beat up the enemy and rounded up “Repeat voters”, people who roamed the voting polls voting several times a day under assumed names.
Working the same area was Eastman’s rival, a dapper and intelligent little thug named Paulo Vaccerelli aka Paul Kelly, leader of the equally vicious and predominantly Italian Five Points Gang.
Paul Kelly's headquarters, the building still stands today
Vaccarelli was born around 1876 in Italy and later immigrated with his family to New York City. He established himself first as a professional bantamweight boxer (Where he changed his name, Irish fighters generally drew a bigger ticket) and then later as a gang leader.
Unlike the rough and ignorant Eastman, Paul Kelley dressed well, in a conservative fashion, he was, by standards of the day, well educated, soft-spoken. He could speak English, Italian, Spanish and some French and went out of his way not to act as a gangster.
As a result, unlike Eastman, he was able to move easily among the different levels of society and was more effective as a leader. He held court at the New Brighton Dance Hall, essentially a dive on Great Jones street and like Big Jim Colosimo’s place in Chicago, it was frequented by the New York upper class when they felt the need to slum. But in the end, Kelley was no better or no worse than Eastman, he was a street punk, a thief and a pimp who headed a terrorist gang of dangerous thugs thought to number at least 1500 strong. The gang controlled the area between Broadway and the Bowery, and Fourteenth Street, City Hall Park, the Five Points District in Manhattan’s Lower East Side, Chatham Square, the Bowery and part of Chinatown. From his gang came Chicago’s Johnny Torrio, Frankie Yale and Al Capone.
At the time, the Five Point’s (The name derives from the five pointed star once formed by the intersections of Anthony, Little Water, Orange and Mulberry Streets) was New York’s premier slum, by 1900, the height of the street gangs power, the once massive Irish ghetto had more or less become an immigrant Italian neighborhood. It was beyond poor, it was impoverished and forgotten. Five Points was, more or less, an Irish neighborhood, but by 1900 Italian immigrants had flooded into the area.
It was lined with slaughterhouses and malaria broke out regularly due to the filthy conditions and the damp ground, which covered what, had once been a small pond. It was densely overcrowded (About 3000 people per half mile) and filled with violent, senseless crime area. Garbage and chamber pots were dumped out of the windows onto the streets.
In 1832 alone, full one-third of the people of the Points succumbed to cholera. In 1854 alone, 1 out of every 17 people died. It was home to approximately 270 saloons and over 500 bordellos. Barefoot children wandered the streets unsupervised, most of them dressed in rags, playing on the bodies of dead horses and around puddles of human waste. Their idols were the hundred, perhaps thousands of hoods who roamed the neighborhoods. By age 8 or 9, most of them would be gang members as well.
Five Points was the home to gangs like the Dead Rabbits, Forty Thieves, Kerryonians, Chichesters, Plug Uglies, Roach Guards and the Shirt Tails, wanted murderers, thieves and pickpockets all.
Both gangs grew out of the dirt-poor Jewish, Italian and Irish immigrants who flooded into New York in the late 19th century, for whom a life of crime was often the only alternative to starvation.
Monk Eastman’s feud with Paul Kelly began over a strip of territory between Mike Salter’s dive on Pell Street and the Bowery. Eastman claimed domain over the territory from Monroe to Fourteenth streets and from the Bowery to the East River. Kelly stated flatly that his kingdom included the Bowery and any spoils found in this area.
As the Five Pointers grew in size and increased their rackets, it was only natural that territorial fighting broke out between them and in 1901 the Monk barely escaped an assassination attempt when one of Kelly’s men shot him twice in the abdomen. The Monk lived and the war was on.
Two and a half year later, in the summer of 1903, a street battle broke out between the two sides when the Five Points Gang held up a gambling hall owned and guarded by the Eastman’s.
The heavily armed Eastman’s opened fire and killed one of the Five Pointers. The remaining robbers ran off and regrouped several blocks Away and phoned Paul Kelly, giving him a completely different version of event over what had actually happened (Kelly had not sanctioned the robbery) Kelly rounded up his men and rushed to Rivington Street in a carriage. Meanwhile, the Eastman’s had called in reinforcements and the two gangs clashed in the middle of the street. Fighting continued for almost an hour over a two-mile-long battlefield. Over 100 gangsters took part, some of them being members of an Irish gang called the Gophers, who showed up and started firing pistols in to the fray, not caring who they hit.
In all, about several hundred (estimates range from 100 to 200) combatants were in the fight that took place over a two mile area, eventually, after five hours, beaten off the streets by 500 patrolman, but the fight only ended when the gangsters ran out of bullets. Remarkably, only 3 people were killed and 7 injured. The Rivington Street riot was to0 much, even for Tammany Hall.
“Big Tim” O’Sullivan, paid by Tammany to keep the gangs in check, delivered the bad news. Because of the media attention on the brawl, all of the gangs operations were going to be raided and shut down for a while. It was all for show, but it had to be done.
To smooth over the political bosses and the newspapers, Monk Eastman and Paul Kelly were forced to shake hands at party hosted by the Democrats.
When war threatened to erupt once more, the Sheriff of Manhattan Tom Farley suggested that the two-gang leaders fight man-to-man, the winner gaining complete control over the Lower East Side. Kelly and Eastman agreed, but afterwards there were disagreements over who had won the contest. Monk Eastman was not around long enough to see the fresh outbreak of violence.
In 1904, a member of the Pinkerton Detective Agency stopped Eastman from beating a man senseless in broad daylight on a Manhattan street. Eastman fired off 12 shots at the private investigator and was arrested shortly afterwards. On February 2, Eastman was convicted of the assault and received a 10-year sentence in Sing-Sing prison.
With the Monk away in prison, the Eastman’s fell under the command of the far less violent Max “Kid Twist” Zwerbach. For several weeks’ peace reigned on the streets and as far as the Five Pointers were concerned, with Eastman in jail, the war was over. However, as far as Kid Twist and the Eastman’s were concerned, the war wasn’t over, it was temporarily halted.
Eventually Kid Twist invited an Irish gangster named Richie Fitzpatrick, an alley of the Five Pointers, to a peace conference and stupidly Fitzpatrick went. Kid Twist killed him immediately. Shortly afterwards, Kid Twist’s lieutenant Vach “Cyclone Louie” Lewis murdered several members of Fitzpatrick’s gang.
Since the Five Pointers couldn’t prove the killing and needed to concentrate on business, the Fitzpatrick murder was overlooked. Four years later, Kid Twist and Cyclone Louie got into a fight in a Manhattan bar with Louis “The Lump” Pioggi, a noted Five Pointer. Outnumbered,
Pioggi leaped from a second story window to escape his attackers, breaking his ankle in the fall. Pioggi took his complaint to Paul Kelly and shortly afterwards both Kid Twist and Cyclone Louie were ambushed and killed.
Following Kid Twist to the leadership of the Eastman’s was Big Jack Zelig, a racketeer from the Bronx who relocated to Manhattan’s West Side. In 1911, a Lt. Charles Becker of the New York Police hired Big Jack Zelig to kill Herman “Beansie” Rosenthal. Becker was using his badge to extort money from New York criminals. Most paid, but as his demands grew more and more outlandish, Rosenthal refused to pay and threatened to expose him, assuming wrongly that the protection money he paid to Arnold Rothstein would protect him from Becker.
Charles Becker was originally from Sullivan County in upstate New York, and moved to New York in 1888 working as a bouncer for while In the Bowery and gained a reputation as a two fisted fighter who could handle himself. It was at this point that he met Monk Eastman.
Through Eastman, Becker probably met Big Tim Sullivan, then a state senator and Tammany’s man in the Tenderloin District (Now the area of Times Square, where Madison Square Garden sits between 7th and 8th Avenues, stretching from West 31st to West 33rd, on the western edge of the old district. Manhattan’s world renowned Garment District, home to one-third of all clothing manufactured in the United States, lies partly in the old Tenderloin. ) who oversaw all graft and bribery in Manhattan. Sullivan placed Becker on the police force in 1893.
Becker wasn’t much of a cop. Several times he was investigated and brought to departmental trials on charges of brutality and false arrest. In 1896 he mistakenly shot and killed an innocent bystander while chasing a burglar and then tried to cover up the shooting by claiming the dead man was a known burglar. He was suspended for 30 days.
In 1898, Becker jumped into the Hudson River to rescue a drowning man. Then it was learned that Becker has paid the man $15 to jump in the river so Becker could be a departmental hero and hold on to his job. As punishment, the department transferred him to the 16th precinct AKA the Tenderloin, the heart of corruption and easy money.
The Old Fourth Ward AKA the Tenderloin was located on the West side of midtown Manhattan between Fifth and Seventh Avenues. During the 1860s, its boundaries ran from around West 24th northwards to West 43rd. This area is considered the original Tenderloin.
As the 19th century progressed, the Tenderloin extended its boundaries, reaching as far south as West 20th and northwards into the West 50s and 60s. At the turn of the 19th century, the area was populated by African-Americans who had fled lower Manhattan.
New York’s first Red Light District was the Bowery however as the Bowery spiraled downwards the Tenderloin took its place.
The original Tenderloin district: from 24th Street north to 40th, between Fourth and Seventh Avenues housed Satan’s Circus, one brothel after another that offered every type of depravity that could be sold. The name came from the reformers in the 1870s.
The best-known club in the area was the Haymarket, located on Sixth Avenue, near 30th Street. It opened after the Civil War, and would remain in business until 1913. It was originally a theater, the Haymarket, and then reopened as a saloon where women drank free, while men had to pay a quarter cover charges to cover the dancing, peep shows and private sexual entertainment in private boxes.
There was Billy McGlory’s Armory Hall. McGlory had once been the leader of the Forty Thieves gang leaving it in the 1870s to enter the saloon business. McGlory’s was the favorite watering hole of the Five Points, the Old Fourth Ward and the Bowery, gangs.
The bouncers were gang members from Five Points, and they walked through the bar carrying bats and guns. Drunks were rolled by prostitutes. There was also the Cremorne at West 32nd and Sixth, the Star & Garter at West 30th and Sixth, Sailor’s Hall on West 34th, Buckingham Palace on West 27th, Tom Gould’s on West 31st and Egyptian Hall on West 24th at Sixth.
The tenderloin was the place to shop in the day and at night the place for gambling, sex of all types and all night dance halls. The area took it’s name from a remark by another cop Captain Alexander S. Williams AKA Clubber Williams. In 1876, he was transferred to the 19th, where his superiors hoped he could make a difference. Williams was transferred into the old Fourth and remarked “I’ve had nothing but chuck steak for a long time, and now I’m going to get a little of the tenderloin.”
On the weekends, the place was packed with tourists, soldiers, drunkards, prostitutes and squads of police. The bordellos in the Tenderloin ran the spectrum, from cheap dirty houses to expensive madams. Dollar houses were located from West 24th up to West 40th. Five-dollar houses littered the side streets from West 41st up to West 60th. A bordello could employ anywhere from 10 to 30 women.
The most expensive bordellos in New York City could be found on Sisters’ Row, on West 25th near Seventh Avenue. It consisted of seven adjoining buildings owned by seven sisters from New England. Callers were not admitted unless they wore evening clothes and carried flowers. They were provided with fancy clothes, pianos, champagne, food and free medical services. The women were also schooled in manners and culture. They were taught to play piano, sing and recite poetry. And they were allowed to keep a large percentage of the proceeds.
At the other end of the spectrum were the cheapest houses, along the low West 20s. The women who worked these houses were poorly fed, in poor health and poorly treated by both their customers and the owners. Even food wasn’t provided for them free. Most were ravaged with some form of venereal disease and had no access to a physician, unless they paid for it themselves.
All of the bordellos of the Tenderloin paid protection money to the police precinct. One bordello, located on West 27th Street, kept detailed records of its pay-offs. The figures are startling. In a one-month period in the 1880s, the bordello, which employed 30 prostitutes, paid out the following sums:
Saturday & Sunday: additional $1.00
Sergeants: .00 every 2 weeks
Lieutenants: .50 every 2 weeks
Inspector: first-time initiation fee; then every month
Sergeants & detectives: .00 every 2 weeks
Ordinary plain clothes officers: .00 every 2 weeks, plus gifts*
The police could raise their fees at any time, and without notice. If a bordello was unable to afford the increase, the police would simply shut them down and turn the girls out into the street.
Becker became the bagman for the local police captain which earned him $8,000 a year at a time when a police officer made less than $3,500.In 1910, Police Commissioner Rhinelander Waldo formed special squads to break up the street gangs that ruled Lower Manhattan and somehow Becker was placed in charge of the unit. Becker, of course, used the unit as a legal shake down tool and grew rich. Then the Rosenthal problem happened.
Big Jack Zelig subcontracted the killing to a thug named Harry Horowitz AKA “Gyp the Blood” who led a group of thieves called the Lennox Avenue Gang.
Four members of the Lennox Avenue Gang shot Rosenthal in the Metropole café. All four were arrested. When Becker was slow in getting them released, one of the men, the getaway driver, talked and Becker was arrested. On July 30, 1915, Lt. Becker was led to the gas chamber at 5:30 AM. At the signal 2,000 volts were sent into his body but didn’t, somehow, kill him. A second higher jolt did. Kid Twist was already dead, executed by the state for the Rosenthal murder.
The Eastman gang then fell under control of Big Jack Zelig. In 1911, Big Jack Zelig was wounded in a badly botched hold-up in. His two top lieutenants, Jack Sirocco and Chick Tricker, assuming he was dead, left him on the streets. Zelig was arrested, but used his political pull and was released. Sirocco and Tricker, afraid that Zelig would hunt them down for deserting him on the street, hired a thug named Jules Morell to kill
Zelig. However, Zelig was warned about the murder and quickly murdered Morell. The murder did little but to spark a civil war within the Eastman’s which ended several months later on October 5, 1912 when Zelig was shot dead by a hood named “Red” Phil Davidson.
In June of 1909, Monk Eastman was paroled from Sing-Sing and returned to the East Side, but found himself without a kingdom. The Eastman’s had more or less fallen apart and the Monk was unable to put them back together again. The civil war sparked by Zelig had taken out some of the gangs best men. With little else to do, he reverted to pick pocketing and dope peddling.
From 1912 to 1917 the Monk was in and out of prison on various charges ranging from opium dealing, robbery, and fighting. Then, in 1917, at age 44, he enlisted in the New York National Guard under the name of William Delaney.
By all reports, as part of the 106th Infantry, 27th Division, O’Ryan’s Roughnecks, Eastman proved to be a fearless warrior on the frontlines
He was discharged from the service in April of 1919 and as agreed Governor Al Smith restored his citizenship. By the Monk returned to dope peddling and street crime. His day was over. In 1918, Monk stole a car belonging to Jules W. Arndt, aka “Nicky Arnstein” as close friend of mastermind of the Underworld Arnold Rothstein who had once employed Eastman as a collector for his money lending operation. Rothstein found Eastman and explained that the car belonged to a friend and Eastman personally delivered the car back to Arnstein and made his apologies.
On December 26, 1920, Monk Eastman was shot and killed in front of the Blue Bird Café, a speakeasy by Jerry Bohan, a corrupt Prohibition Enforcement Agent. Bohan put five slugs in the Monk Eastman’s army buddies Hank Miller and John Boland, put up the funds for a military burial with full honors at Brooklyn’s Cypress Hill Cemetery. Over 4,000 people attended the funeral, most of them simply gawkers who never knew the Monk.
“Mr. Edward Eastman did more for America than Presidents and generals,” Boland announced. “The public does not reward its heroes. Now they are calling Mr. Eastman a gangster instead of praising him as one of those who saved America. But we’ll do the right thing by this soldier and give him the funeral he deserves.”
The Monk’s corpse was dressed in full military regalia, wearing his service stripes and American Legion pin. On his coffin was a silver plate inscribed “Our Lost Pal. Gone but Not Forgotten”
As for Bohan, he was arrested for the murder and sentenced to prison on first-degree manslaughter charges, severed several years and was released in 1923.
In 1905, Paul Kelley closed the New Brighton and later moved his operations to Harlem and Brooklyn where he became a labor union organizer and fought for control of the shipping docks. He died from natural causes on April 3, 1936 and was buried in the Calvary Cemetery in Brooklyn.
The gang he left behind was awesome in its power and size. Over the years of his reign, Kelly incorporated smaller gangs in the Five Pointers such as the once mighty Plug Uglies who he took in with him 1900. It was a tactic later used by Kelly’s student Johnny Torrio after Torrio took control of the Chicago mob.
Torrio fell under Kelly’s control in 1905 when the Five Pointer incorporated the James Street Gang led by Torrio and others. One of Torrio’s bosses was a hood named Jack Sirocco, Kelly’s chief lieutenant, a role that Torrio filled after Sirocco defected to the Eastman’s.
Kelly taught Torrio how to dress, talk and how to set up legitimate
Business fronts. Initially, Torrio was taken with Kelly but eventually grew discouraged at the endless violence he created while he spoke of peace and prosperity. Shortly afterwards, Torrio was summoned to Chicago to work with his cousin, Big Jim Colosimo.
Taking Torrio’s place were Charlie “Lucky” Luciano, Al Capone, Frankie Yale and others. With the advent of Prohibition, the gang slowly lost power and, by 1922, gradually disappeared.
The Tenderloin, after Charles Becker’s execution, things changed. The Casino pulled out and the brothels started to close in fear of being brought to trail in wake of the Becker scandal. Business owners fled the area. By 1921 it was all gone.
As for the Five Points section, a massive federal court house no covers most of the area, an ironic end to the place that gave birth to the American gangster
Thirty-one year old Johnny Torrio arrived to Chicago in 1909 and a few weeks later three Blackhanders, who had been tormenting Colosimo, were found shot to death under the Rock Island Railroad overpass on Archer Avenue. A while later, another Backhander and Levee regular named Sunny Jim Cosmano tried to extort Colosimo down for $10,000 and was shot in the stomach.
For a while Torrio went back and forth between New York and Chicago, he still had business interests in Brooklyn with gangsters Frankie Yale and Paul Kelly. Torrio was soon supervising Colosimo’s other places as well, all of which he put on a sound business basis, by cutting operating costs. He did the same with Colosimo’s gambling dens and saloons and then took over the Colosimo-Van Beaver white slave ring and made it the Midwest’s largest.
In 1911, Torrio bought a car, fire engine red, “Pimp red” the police called it and opened the Four Deuces at 2222 South Wabash, not far from Colosimo’s café. The Four Deuces far and away different from Colosimo’s café; Rather it was a run-down building with a cheap plywood bar and a brothel upstairs. Torrio’s office was in the back of the tavern, a simple desk drowned in the paper of all of Colosimo’s various enterprises. In 1912, Torrio married Anna Jacobs. They lived in a large leased apartment on the South side. Torrio’s private life was lived miles and worlds away from the Levee, from the prostitutes he ordered beaten into submission, the drunks he had rolled, the loan sharking victims he ordered beaten close to death or the Blackhanders he had gunned down.
He had few if any vices. He never smoked, drank or gambled. He ate little, never swore and preferred not to hear it. He arose early each morning, and put in a ten-hour day. He returned home each night at about six for a light dinner with his wife, and except for the occasional play or concert, he preferred to stay home nights listening to the radio in slippers and dressing gown.
By 1907, the Levee was going stronger than ever. It was now at least two miles long, had 119 brothels with 686 prostitutes turning tricks around the clock for an average of $2.00 per customer. But, its opponents refused to give up in their efforts to shut the Levee down. In December of 1909 the Chicago assembly of churches, 600 strong, demanded and received a city investigation, which accomplished nothing. Then, on March 5, 1910, Mayor Fred A. Busse appointed a 30 man Vice Commission to examine the vice situation.
Armed with what was then a massive amount of money, a $5000 grant from the city council, and one chief investigator, the Commission sent detectives into nearly every gambling resort and brothels in the city. As a result, reports were written on every possible aspect of the vice trade from how women were lured into the business and so on.
On April 5, 1911, the commission presented its report, 399 pages, to the mayor’s office. The report used information gathered by detectives about the Levee and three smaller red-light districts and stated that the vice business in Chicago produced an amazing 15,699,499 dollars a year in vice or about 158,000,000 dollars by today’s standards.
Pressures were put on white slavers. Colosimo was a prime target after one of the women he had transported on his Chicago, Kansas City-St. Louis circuit went to the police in New York and turned evidence on Colosimo. While prosecutors awaited the indictments for Colosimo, Torrio and the Van Beavers, the witness was whisked away to Bridgeport, Connecticut for safekeeping.
Torrio, using his New York contacts within the Five Points gangs, found out where the woman was in hiding. Several days’ later two men who had identified themselves as federal agents placed the women in the car and drove away. She was found shot to death with 12 bullets, her body sprawled across a gravesite in Bridgeport. Without a witness, the case against Colosimo was dropped.
Still, the pressure was on. On Wednesday, September 25, 1912, on evidence gathered by the Morals squad, five Levee brothel owners were indicted, including A.E. Harris, the Democratic precinct committeeman of the first ward. Then, on Friday, October 4, 1912, the first blow to wipe out the Levee came when warrants were issued for 135 brothel owners, largely because the crusaders wouldn’t let up on the police. The police, largely on the payrolls of the brothel owners, warned the club owners about the pending mass raids and the Levee broke into a panic. The warrants were issued near midnight when the Levee came to life; those who escaped arrest left the city never to return.
Things came to a head in the Levee in April of 1914 when a police sergeant with the Morals squad was stabbed to death while investigating a murder. A few days later, on July 16, 1914 the front line officer in charge of the Morals squad, Inspector W.C. Dannenberg, led a raid on the Turf, a huge brothels on the corner of Twenty-Second Street in the Levee.
After the prostitutes were rounded up and tossed in the paddy wagon, an ugly mob appeared and surrounded them and started throwing stones. Behind the mob, sitting in the back seat of his red Cadillac was Johnny Torrio and two of his gunners, Roxie Vanilli and Mac Fitzpatrick.
Inspector Dannenberg took the arrested prostitutes on to the police station for booking and left his officers behind for crowd control. As the crowd grew more violent, the plainclothes police drew their service revolvers and threatened to shoot. At that very moment two uniformed policemen assigned to the Levee came around the corner, and not recognizing the officers from the Morals squad, opened fire. At that same time Torrio’s gunners, Vanilli and Fitzpatrick climbed out of Torrio’s car and opened fire as well. When the gunfight ended, four of the police were shot; one was dead with three wounded. Vanilli was wounded but escaped. An autopsy performed on the dead policeman confirmed that he had been killed with dum-dum bullets, oversized shells that expand when fired, a type not used by the police but normally preferred by gangsters.
After the shootout, the police came down hard. Van Beaver, Joe Moresco and Vanilli were locked up but set free the same day; Captain Ryan, Colosimo’s own police captain in charge of the Levee was transferred out and a new commander was brought in who finished the closing of the Levee forever. The Morals squad succeeded in closing most of the big, easily raided houses so the Procurers replaced them with apartments, “call flats” and Funkhouser estimated that by 1919 there were at least 30,000 call flats operating across the city.
The Levee’s death was stopped, temporarily; by the election of the mobs own mayor, Big Bill Thompson. In 1915 Thompson won the mayoral race in Chicago with the biggest plurality ever given to a Republican in that city. After he was elected, Thompson spent the next six months breaking every one of his campaign promises, and, as a result, the city was wide open. The politicians downtown were getting a share of everything because Thompson had invented an organization called the Sportsman club in which every big-time gambler and Procurer, police captain and council member belonged to by paying annual “lifetime membership” dues of $100.
Thompson restored Jim Colosimo’s liqueur license, fired Major Funkhouser and stripped the Morals squad of most of its power. But even with a friend like Thompson in the mayor’s office, Johnny Torrio could read the writing on the wall; the days of the Levee were ending. Torrio looked around him and saw that the automobile, relatively new to the American scene, was changing everything. The population was moving out of the city and Torrio decided, and Colosimo agreed, that they would follow. Torrio opened his first brothel outside the Levee in the tiny village, a hamlet really, of Burnham on the Illinois Indiana border and about 18 miles from the heart of the Levee.
The president of the village, “The Boy Mayor” was 19-year-old John Patton. Patton was ready, willing, and able to take as much graft, as Johnny Torrio was willing to dole out. Torrio’s first roadhouse was open twenty-four hours a day with ninety prostitutes working three shifts. By its first month in operation the roadhouse had grossed $9,000. With that success, Torrio and Colosimo opened the Speedway Inn and put Leveeite “Jew Kid” Grabiner in charge.
The steady flow of customers came from the nearby steel mills and oil refineries that had a steady paycheck and a need for some predictable excitement every now and then. Torrio was smart enough to ensure that none of his growing number of suburban roadhouses stood more than a few feet from the Indiana line in the event of a raid by the County or state police. In that case Torrio, his employees and his guests could avoid arrest by simply walking over to the next state. As an added precaution Torrio set up an unbeatable alarm system for each of his brothel. He paid gas station owners and fruit stand peddlers that dotted the roads out to his places. If a raid was on the way they called Torrio who sounded a general buzzer alarm inside each of his brothels and the places were emptied. Torrio was so proud of his system that he held drills to make sure everyone understood their duties. Torrio allowed the Boy Mayor to stay in office, but Johnny Torrio ran the village. He and he alone decided who did business there and who didn’t.
In 1918, Torrio got word that one of his own bodyguards had been paid to kill him off. Torrio killed him instead and then he sent for Al Capone who arrived in Chicago with his wife and newborn child in the winter of 1919 with two guns beneath his suit coat. Capone began as a $35 a week bouncer at one of Colosimo’s brothels. He was already suspected in the beating death of prostitute in Brooklyn.
Colosimo, left, his father, and a young Johnny Torrio
Torrio was growing impatient with Colosimo. He couldn’t see the opportunity ahead with prohibition, he was too cautious and the organization behind Colosimo lacked discipline. Torrio saw prohibition coming and saw the money in it. Colosimo was already rich and he told Torrio to stick to the basics: women and gambling. Prohibition would come and go, he lectured, but women and numbers would last forever. Torrio was rich too but he was also greedy. Before prohibition started he was already making $1,000,000 a year from prostitutes and gambling and he wanted more.
Torrio decided that he would organize Chicago’s gangs but when Torrio broached Colosimo with the idea, Colosimo was too entangled in his upcoming divorce he paid the idea no mind and ordered Torrio, again, to stick to basics.
The reason for Colosimo’s absentmindedness was love. In 1913 the news reporter Jack Lait came into Colosimo’s café and ranted and raved about a young actress appearing at the South Park Avenue Methodist Church and he suggested Colosimo hire the young woman and put her in his floorshow. Colosimo agreed to go and see the show himself and when he did he fell in love with 19-year-old Dale Winter of Ohio, who dreamed of a career as an opera star. She was chaperoned with her mother with whom she traveled. Colosimo left his wife and married Dale, telling Johnny Torrio, “This is the real thing.”
“It’s your funeral,” replied Johnny.
Dale did her best to add some polish to Colosimo, and slowly Colosimo started to change. He toned down his clothes colors for more conservative tones. She pulled him away from his Levee friends and politico types and soon the word went out, “Colosimo is getting soft.” which was essentially true.
When the divorce came through on March 20, 1920, Victoria said, “I raised my husband from a boy to a man for another woman.” She took a $50,000 settlement. Twenty-four hours later Colosimo married Dale, the couple honeymooning in fashionable French Lick. Afterwards they returned to their mansion at 3156 Vernon Avenue and took Dale’s mother in with them.
According to reporter Ray Brennan, Torrio, whom he recalled as a “little torpedo for hire, Johnny Torrio whose pop eyes and pursed mouth gave him a perpetually surprised expression,” ... had meetings with Chicago’s other leading gangster, Dion O’Bannion, the Genna’s and the Aiello’s, and discussed Colosimo’s pending assassination. They apparently agreed that it needed to be done.
A week after Colosimo’s return, Torrio phoned him to say that two truckloads of whiskey were due into Colosimo’s café and Torrio would need to have Colosimo there for paper work and other odds and ends. Torrio was very specific about the time; Colosimo had to be there at 4:00 p.m. sharp. Annoyed at having to be troubled with the details of whiskey shipments, Colosimo agreed to be there and on Tuesday, May 11 he left his home at 3:45, decked out in his usual diamonds and pearls, a. 28 short nosed pistol stuffed in his right hip pocket. He kissed his wife good-bye and promised to have the chauffeured car sent back so she and her mother could go shopping. The driver noted that all the way to the café Jim sat crouched down in the back muttering to himself in Italian.
The driver left Colosimo in front of the café at almost 4:00. Colosimo walked through the dark and empty café and went directly to his massive office in the rear and met with his secretary, Frank Camilla and the chef Caesarino and discussed the day’s menu. They said later that Colosimo looked troubled. He asked them if anybody had called him and when they said nobody had called he looked concerned and tried to reach his lawyer Rocco De Stefano by phone but couldn’t reach him. It was about 4:25. Colosimo walked out to the half-darkened lobby where his killer or killers were hiding in the glass-paneled telephone booth. The murderer fired two shots through the glass when Colosimo passed him, the first shot hit Colosimo in the head behind the right ear, and the second missed and hit the wall. Colosimo hit the tile floor face first. The killers rushed out from they’re hiding place, ripped open Colosimo’s shirtfront, withdrew his long leather wallet and fled. Inside the restaurant, there was a place set for one person, who had apparently been eating Italian ice cream with a glass of apricot brandy. The killer left a message on the check: “So long vampire, so long lefty.”
The police questioned more than thirty suspects including Johnny Torrio who gave a fine performance as a grief stricken relative, “Colosimo and me,” he told the police, “we was like brothers.”
Police took in Colosimo’s brother-in-law, Joe Moresco, for questioning, but he had an alibi. So did Victoria and her new husband, they were in Los Angeles on the day Colosimo was killed. In a citywide police dragnet, police picked up Frankie Yale, as he was about to board a train back home. Soon afterwards Detectives heard a rumor that Torrio had paid Yale $10,000 in cash to come into New York and kill Colosimo. Years later, Capone told the playwright Charles MacArthur that he pulled the trigger on Colosimo on orders from Johnny Torrio. But a porter in the café said that he had seen a man hiding in the shadows and gave a description, which fit Yale so the police brought the porter face to face with the gangster, and the porter changed his mind.
On May 14, 1920, Chicago witnessed its first of many big money, lavish gangster burials. Colosimo’s bronze coffin, itself worth thousands of dollars was covered in thousands of floral wreaths from everybody who was anybody.
Five thousand 5,000 mourners, one thousand members of the First ward Democrats club, two brass bands playing dirges and fifty-three pallbearers, actual and honorary to the cemetery. Among the honorary pallbearers were nine aldermen, three judges, two United States Congressmen, a state senator, the state republican leader and one Assistant State’s Attorney from the Cook County State’s Attorney’s office
Archbishop George Mundelein refused to allow his priests to bury Colosimo with any rites of the Church or lay him to rest in a Catholic cemetery. Dale Colosimo found a sympathetic Presbyterian minister named Pasquale De Carol to perform the burial rites inside Colosimo’s mansion on Vernon Avenue.
Capone, still an unknown flesh peddler and hustler and well below Colosimo’s station wasn’t invited to the funeral, but showed his grief by observing the old Italian custom of not shaving for three days.
Colosimo’s lawyers could only find $67,500 in cash and bonds and another $8,894 in jewelry in Colosimo’s estate. They had expected to find at least $500,000 in cash. Where the rest of Colosimo’s fortune went, nobody knows and nobody ever found out. That secret died with Colosimo.
Dale Winter’s Colosimo lay grief-stricken in her bed for ten days when word came that she had not been married to Colosimo due to a fine point in Illinois law which required that a couple take one year interval between divorce and remarriage. As a result of this oversight, Dale had no legal claim to what was left of Colosimo’s estate, however Colosimo’s family did grant her $60,000 in bonds and diamonds and gave another $12,000 to Victoria not to contest the split. The rest went to Colosimo’s father Luigi.
For a while Dale made a try at running Colosimo’s café but she just didn’t have the same touch for the business that Colosimo had so she sold her share to Mike the Greek Potzin who already had an interest in the place anyway.
Dale and her mother returned to New York and became a Broadway success. She remarried to an actor in 1924 and was active in the theater throughout the thirties when she retired to San Francisco in the late 1940s.
With Colosimo’s death, old world crime left Chicago forever. The end of the Mustache Petes, the old bosses who confined their activities to the boundaries of their neighborhoods.