Since most of my work on these pages are about New York gentleman,
I had to included one of the New York boys who made his way to Chicago.
It is only fitting that I included a little Chicago history  to go along with:
Alphonse ( Scarface ) Capone.

  Year 1871, the Great Chicago Fire.
Since little rain had fallen during the summer, the frame buildings of the city were as dry as
timber. The fire broke out in the barn of  Patrick O'Leary in the rear of 137 De Koven St., on
Sunday October 8. A strong wind was blowing and flames and timbers were thrown into the Loop.
Soon the fire was everywhere, destroying everything in its path. The city jail caught fire, freeing criminals who fled in all directions. 2004 acres in the middle of the city were leveled, 18,000 buildings were destroyed, 3000 people dead, and property damage exceeded $200,000,000.
In spite of General Phil Sheridan's declaration of martial law, criminals had a field day, looting every storefront in sight. In time, through hard work, pride, and perseverance, the 'City of Big Shoulders' rebounded and was completely rebuilt better than ever. Corruption had run rampant through Chicago politics, being traced back as far as the turn of the century. First Ward Democratic aldermen Michael (Hinky Dink) Kenna and Joseph (Bathhouse) John Coughlin (they were  members of the city council, at that time), were as corrupt as they come.
Until restructuring in 1992, the first ward was the most strategic, containing the Loop, named for the encirclement of elevated railway tracks of the Chicago Transit Authority, the Near West Side, and the Near South Side. Not only were there brothels, and gambling houses, but also fine department stores, restaurants, skyscrapers, the best hotels, and the largest banks. These CTA trains brought thousands of workers and shoppers downtown, contributing to the large financial and economic growth of the city. This was Hinky Dink and Bathhouse John's empire.
Hinky Dink and Bathhouse John were nothing more than an extension of the underworld, and a glimpse into the future of Chicago politics. By 1907 Mont Tennes had become the leader or czar of gambling in the city which was considered the biggest handbook in the country. Protected by Hinky Dink and Bathhouse John, Tennes became rich and powerful by setting up operations in saloons, brothels, and newsstands, not to mention his rings of bookies on the streets. 1907 was also the time during which the first battle for control of the wire service,
the operation which provided handicapping odds on horse races throughout the nation.
The war became so brutal and widespread that even Tennes own home had been bombed.
This war led to a grand jury investigation which determined Mayor Fred Busse and Chief of Police George Shippy were under the control of Tennes syndicate. The flashy well dressed Big Jim Colosimo opened Colosimo's Cafe in 1910,
with the flair that would soon make him the boss of Chicago.
Located at 2126 S. Wabash Ave., Colosimo's Cafe had become the hot spot of Chicago nightlife.
While enjoying national renown, it was a nightly occurrence to see Al Jolson seated next to vice merchant (Mike de Pike) Heitler, or suave whore master Dennis (The Duke) Cooney tabled with John Barrymore and Sophie Tucker. Other notables who frequented Colosimo's Cafe including Marshall Field, Mike Merlo, head of the local Union, the aforementioned Mont Tennes, whose life history according to an Illinois Crime Commission survey, "would disclose all there is to know about syndicated gambling as a phase of organized crime in Chicago in the last quarter century." Gambler Julius (Lovin Putty) Annixter, Charlie (Monkey Face) Genker, labor thug (Izzy the Rat) Buchalsky, black hander Vincenzo (Sunny Jim) Cosmano, and chieftain of Chicago's most powerful strong-arm gang, Dion O'Banion, as well as members of the Chicago Civic Opera, Mary Garden, Louisa Tetrazzini, Amelita Galli-Curci, Titta Ruffo, John McCormick, and the conductor Maestro Cleofonte Campanini. Although Colosimo's Cafe was highly profitable, it was just a fraction of Big Jim's $600,000 annual salary.
Colosimo controlled most of the Levee's brothels, and white slavery rings.
Located at 19th and Armour Ave. was (Bed Bug Row), a cluster of 25 cent cribs of  Negro whores, and the stretch between 21st and 22nd streets held some of the higher class brothels such as French Emma's, the Casino, the Utopia, the Sappho, and the highly storied Everleigh Club, operated by Kentucky born sisters, Ada and Minna Lester. The Levee flourished under Tennes and Colosimo and their penchant for vice, while being protected by the First Ward who now had almost every powerful member of Chicago law enforcement on the payroll.
Fifty wide open gambling joints operated in the loop alone.
Following an investigation in 1911, the Civil Service Commission revealed police raids were made only under the instruction of Tennes or his top lieutenant (Mike de Pike) Heitler, and then only against those who competed against the Tennes, Colosimo syndicate. Chicago became so wide-open and over run by corruption and sleaze that the Lester sisters, thinking they were untouchable, made the mistake of circulating a brochure advertising the accommodations of the Everleigh Club and its girls. Because of great public outcry, Mayor Carter Harrison decided this was giving the city a bad name, and ordered a crackdown in the Levee, especially against the Lester sisters. Violence and murders erupted. Several brothels and gambling joints were raided and busted up.
The killing came to a head on July 18, 1914 when vice lords shot and killed Detective Sergeant Stanley Birns, while wounding another officer. Harrison was a good mayor, but he had campaigned to cater to the huge German vote. When World War I broke out, Harrison's plan backfired and his relatively unknown Republican opponent, William Hale Thompson defeated him. This became a huge victory for the underworld, as (Big Bill) promised a wide-open city, and in later years made good on that promise. The first of many highly important indictments occurred on January 16, 1917. Indictments charging bribery and graft were returned, implicating eight men including Chief of Police Healey, another police Captain named Tom Costello, William Skidmore, a saloon keeper and gambler; and two other policemen. Also at this time a gang of young sicilian street guys, who went by the nick name of the Circus Cafe Gang, were making a name for themselves.
By 1919, thirteen year old Tony Accardo had become a member and was well on his way to becoming the man who perfected organized crime in Chicago. As Big Jim's empire grew, he soon realized he needed someone strong to help control it. In later years this position would become known as sotto capo, or under boss.
Colosimo chose to reach out to New York where his nephew, Johnny Torrio was making waves as leader of the James St. Gang. Although small in size he made up for that with his brains.
He and his roughneck pals took over the waterfront of the East River in lower Manhattan.
Torrio, realizing a great opportunity, agreed to come to Chicago to become the number one man to the boss.
Soon after Torrio came to Chicago a monumental ruling came down.
On October 18, 1919 the National Prohibition Act was passed, effective January 16, 1920.
Torrio had the foresight to capitalize on this even though Colosimo didn't agree.
In 1920 while Colosimo was honeymooning, Torrio sent for a killer.
John had plans for the elimination of Uncle Jim.
He arranged for Colosimo to be situated in the vestibule of his restaurant awaiting the delivery of two truckloads of whiskey by Jim O'Leary, the gambling boss of the nearby Stockyards district.
G
The first two shots hit him square in the head.
G
(Big Jim) was dead before he hit the floor.
G
A popular misconception is that the man Torrio sent for was Frankie Yale (real name Uale), but it was not
(as evidenced in later years was released through discussions heard on FBI wiretaps.)
The killer had been a member of New York's powerful Five Points Gang,
and was on the lam from police for two murders in New York.
This man's name was Alphonse Capone.
Another interesting note is, at Colosimo's funeral the honorary pallbearers included three judges, an assistant State's Attorney, a Congressman, a State Representative, and numerous aldermen including Hinky Dink. On May 10, 1920 a hearing conducted by the US Judiciary Committee made it quite clear that Chicago was the undisputed headquarters in the country for crime and vice. Interestingly enough this was acknowledged in 1921 by new Chief of Police Charles C. Fitzsmorris, who candidly admitted that a large percentage of his officers were engaged in the illicit liquor business. Mayor Thompson delivered as promised, a wide-open city, turning a blind eye to Torrio's illicit empire. It was taken a step further when Warren G. Harding was elected President.
Arguably Harding's cabinet was the most corrupt in history, giving the Syndicate a Mayor, a Governor (Len Small), and the federal administration on their payroll. Contrary to popular belief it
was Johnny Torrio who organized crime in Chicago's roaring twenties, and not Al Capone.
Torrio took Colosimo's empire to new levels,
building substantial wealth by moving into the suburbs, especially Cicero.
Also included were Burnham to the South, and Stickney to the Near South West, as well as owning the West Hammond and Manhattan breweries.
Torrio's reign gave him vast power and riches, and coupled with the extortion muscle run by Al Capone, they became fiercely feared as well. It is said that all good things must come to an end, and such was the case when three men, rival North Side gangsters, (Bugs) Moran, Hymie Weiss, and Vincent (Schemer) Drucci, made an attempt on Torrio's life. Capone vowed revenge against these three men and their gang who became a thorn in the Sicilian's side for many years to come.
 
After Torrio recovered, he had decided enough was enough, and turned over the entire empire to his sotto capo, Al Capone.
Torrio returned to his old stomping grounds of New York in (semi retirement), proving that the feud between the New York and Chicago mobs is something that was only written in the newspapers.
About ten years after his return to New York, Johnny Torrio, the man with the brains who was against the violent ways of Capone, was convicted of income tax evasion. A new era in Chicago was set to begin.
 
Enter Al ( Scarface) Capone.
Al Capone is perhaps the most notorious mobster ever. Many movies and books have been created in his honor.
Alphonse Capone was born at 95 Navy Street, January 17, 1899 in a rat infested Brooklyn slum. The fourth of nine children, to immigrant parents from Naples, Italy. Capone left school during the sixth grade after he was beaten by the principal for beating up his tutor. He and his family lived in a rough neighborhood. Al held down a variety of honest jobs from clerk in a candy store to being a cutter in a book bindery. At age eight, he was mascot for the Navy Street Boys teenage gang, headed by Frank Nitto. Older brothers Vincenzo, Ralph and Frank were bona fide members of this gang. Eldest brother Vincent who was a horseback riding enthusiast, often took younger brother Alphonse pony riding, near Clove Lake Ice House Stables in Staten Island. After one of their rides his oldest brother left Brooklyn for good and was not heard from for years. Al joined the James Street Gang, a tough street gang of teenagers and kids run by Johnny Torrio who would himself  become a founder member of the Chicago Mob. Another member was Lucky Luciano, who would later attain his own notoriety. Upset with the area they lived in, Gabrielle and Theresa, Capone's parents, moved their brood to Garfield place. There, Al at age 12, became a member of the South Brooklyn Rippers, another group of teenage hoodlums. He also joined the Forty Thieves Juniors, this was a elite branch of the Five Points adult gang  where Capone later graduated to.  Capone became the prize student of the veteran five point executioner, Frankie Ioele (a.k.a. Frankie Yale). At age 18, his boss gave him a job at the Harvard Inn, a dine and dance joint on the Coney Island waterfront.
In the Summer of 1917, while working as the bartender, greeter and bouncer at the Harvard Inn, he insulted a female guest who was accompanied by her older brother Frank Galluccio and his date. The remark Capone made was "You have a beautiful ass, and I mean that as a compliment. Believe me." The brother was halfway into a drunken stupor, asking for an apology. Galluccio saw Capone walking towards him, Galluccio pulled out a knife with a sharp four inch blade and slashed Al's left cheek. Capone would later tell reporters that his scar was a reminder of his service in France in the "Lost Battalion" during World War I. Capone never fought in France. In 1959, Galluccio confided in an exclusive interview with a reporter that "a punch was not enough to bring Capone down." So he used his street instincts when he pulled the knife. Unfortunately for Capone, Galluccio had underworld contacts in Manhattan and a sit down was ordered by Joe (The Boss) Masseria. Lucky Luciano, Yale, Galluccio and Capone sorted their difficulties out. Capone was ordered to apologize for the insult and Galluccio was ordered to compensate Alphonse for the scars that he inflicted. The cost was $1,000.
In 1918 Capone fell in love with an Irish girl.
Mary was her baptized name but she would be called Mae all her life.
She was almost two years older than Capone.
They married and on December 4, 1918  Mae gave birth to Albert Francis Capone.
Towards the end of 1918, Capone was on his collection rounds for Yale to seek out longshoremen who were late in their Shy lock payments. While making his rounds, he became embroiled in a bitter waterfront barroom brawl in the bathroom with Arthur (Criss-Cross) Finnegan, a low echelon member of  brooklyn's notorious White Hand Gang. When the white hand gang leader (Wild Bill) Lovett heard about the infractions against one of his men, he relentlessly pursued the Italian Perpetrator. Only knowing that it was a "scarred" man, he was unable to find him, and he never brought the "nameless" aggressor to the court of mob justice. Things travel fast in the mob world, and Capone's Brooklyn Mentor, Frankie Yale placed a call to Johnny Torrio in chicago. They concluded that Capone would have to travel west into chicago and join the criminal operations of 'Big Jim' Colosimo and Torrio to avoid a brutal death at the hands of Lovett.
In 1920, at Torrio's invitation, Capone joined Torrio in Chicago to help out his old buddy who was working the brothels in the Windy City for his uncle "Big Jim". Torrio had become an influential lieutenant in the Colosimo mob. Torrio was at the time having big problems with his uncle, Big Jim Colissimo, who did not want to get involved with the booze rackets that Prohibition would bring. The rackets spawned by enactment of the Prohibition Amendment, illegal brewing, distilling and distribution of beer and liquor, were viewed as "growth industries." Torrio, abetted by Al Capone, intended to take full advantage of opportunities. The mob also developed interests in legitimate businesses, as the cleaning and dyeing field, and cultivated influence with receptive public officials, labor unions and employees' associations. Torrio had plans for the elimination of  his Uncle Jim. He arranged for Colosimo to be situated in the vestibule of his restaurant awaiting the delivery of two truckloads of whiskey by Jim O'Leary, the gambling boss of the nearby Stockyards district.
The first two shots hit him square in the head.
(Big Jim) was dead before he hit the floor.
A popular misconception is that the man Torrio sent for was Frankie Yale (real name Uale), but it was not
(as evidenced in later years was released through discussions heard on FBI wiretaps.)
The killer had been a member of New York's powerful Five Points Gang,
and was on the lam from police for two murders in New York.
This man's name was Alphonse Capone.
Torrio soon succeeded to full leadership of the gang with the violent demise of Big Jim Colosimo and Capone gained experience and expertise as his strong right arm.
Together, Torrio and Capone began taking charge in Chicago. Those gangs that would not toe the Torrio, Capone line went to war with them. The most famous of these wars was with the O'Banion Gang from Chicago's North Side. It was this gang that put John Torrio in hospital in 1925. When he finally got out about a month later, he told Capone "Al, it's all yours", took 30 million dollars with him and retired back to Brooklyn.
So, at the age of 26, Al Capone became the leader of one of the worlds largest crime families.
The Capone Mob numbered over 1000 members, the majority stone cold killers. He was a murderer, pimp, extortionist and bootlegger, but the public loved him. Capone was seen in the company of movie stars, big business people and political figures. He restricted the Outfit's activities to those the public wanted,  booze, prostitution and gambling. If the people are given what they want, they are not going to want to stop you!
Al Capone was cheered when seen at public events. Herbert Hoover was booed.
Capone had built a fearsome reputation in the ruthless gang rivalries of the period, struggling to acquire and retain "racketeering rights" to several areas of Chicago. That reputation grew as rival gangs were eliminated or nullified, and the suburb of Cicero became, in effect, a fiefdom of the Capone mob.
Capone surrounded himself with his most trusted mobsters. Frank Nitti, 'Machine Gun' McGurn, Tony "Joe Batters" Accardo. Trust was everything. If you couldn't trust your bodyguards, you would end up whacked. Capone's trust was well placed with his men. And that trust was returned equally.  became known as a man who could be counted on in any event. But even so, Al had to be careful. There were many attempts to rub him out. On one occasion, the O'Banion gang sent a whole motorcade of machine gun happy mobsters past his Cicero headquarters. Over 1000 rounds were fired into Capone's headquarters building but Al escaped without a scratch.
Capone eventually dealt with his enemies. His most famous personal retribution involved the killing of three of his own men, John Scalise, Albert Anselmi and Hop Toad Giunta. These three men were conspiring to have Capone eliminated but Al got wise to their scheme. Capone invited them to a banquet and, after the meal, pulled out a club and bashed their brains in on the dinner table.
Just months prior to this, Capone orchestrated one of the most famous Mob hits of all time.
 North Side gang leader  Bugs Moran, working against the new under world order brought about Chicago's Armageddon which concluded with the St. Valentine's Day Massacre on Feb. 14th, 1929.
Head Line reads:
"Seven members or associates of the "Bugs" Morans' mob were machine gunned against a garage wall by rivals posing as police."
 As successful as the hit was, it was not a winner for Capone. The massacre of the seven north side mobsters was all over the news papers and the public's attitude to gangsters began to change. Wholesale slaughter was not what the public wanted. The hit also focused the efforts of the law enforcement community on Al Capone.
However, Capone had an iron clad alibi when the murders were taking place.
He was at his Miami condo talking to the local district attorney on the telephone at the time.
 
The investigative jurisdiction of the Bureau of Investigation during the 1920s and early 1930s was more limited than it is now, and the gang warfare and depredations of the period were not within the Bureau's investigative authority.
The Bureau's investigation of Al Capone arose from his reluctance to appear before a Federal Grand Jury on March 12, 1929, in response to a subpoena. On March 11, his lawyers formally filed for postponement of his appearance, submitting a physician's affidavit dated March 5, which attested that Capone, in Miami, had been suffering from bronchial pneumonia, had been confined to bed from January 13 to February 23, and that it would be dangerous to Capone's health to travel to Chicago. His appearance date before the grand jury was re-set for March 20.
On request of the U.S. Attorney's Office, Bureau of Investigation Agents obtained statements to the effect that Capone had attended race tracks in the Miami area, that he had made a plane trip to Bimini and a cruise to Nassau, and that he had been interviewed at the office of the Dade County Solicitor, and that he had appeared in good health on each of those occasions.
Capone appeared before the Federal Grand Jury at Chicago on March 20, 1929, and completed his testimony on March 27. As he left the courtroom, he was arrested by Agents for Contempt of Court, an offense for which the penalty could be one year and a $1,000 fine. He posted $5,000 bond and was released.
On May 17, 1929, Al Capone and his bodyguard were arrested in Philadelphia for carrying concealed deadly weapons. Within 16 hours they had been sentenced to terms of one year each. Capone served his time and was released in nine months for good behavior on March 17, 1930.
On February 28, 1936, Capone was found guilty in Federal Court on the Contempt of Court charge and was sentenced to six months in Cook County Jail. His appeal on that charge was subsequently dismissed.
Meanwhile, the U.S. Treasury Department had been developing evidence on tax evasion charges - in addition to Al Capone, his brother Ralph "Bottles" Capone, Jake "Greasy Thumb" Guzik, Frank Nitti and other mobsters were subjects of tax evasion charges.
On June 16, 1931, Al Capone pled guilty to tax evasion and prohibition charges. He then boasted to the press that he had struck a deal for a two-and-one-half year sentence, but the presiding judge informed him he, the judge, was not bound by any deal. Capone then changed his plea to not guilty.
On October 18, 1931, Capone was convicted after trial, and on November 24, was sentenced to eleven years in Federal prison, fined $50,000 and charged $7,692 for court costs, in addition to $215,000 plus interest due on back taxes. The six month Contempt of Court sentence was to be served concurrently.
While awaiting the results of appeals, Capone was confined to the Cook County Jail. Upon denial of appeals, he entered the U.S. Penitentiary at Atlanta and later on the island prison of Alcatraz in San Francisco harbor.
Capone's time in Alcatraz was not easy. Although he could gain favor from some with enticements of money, other criminals were not so taken with the mighty Al Capone. There were many attempts on Capone's life in Alcatraz. He was stabbed in the back and attempts were made to poison him, strangle him and stick him in the head with a device called a sash weight.
On November 16, 1939, Al Capone was released after having served seven years, six months and fifteen days, and having paid all fines and back taxes.
Suffering from paresis derived from syphilis, he had deteriorated greatly during his confinement. The infection spread to his brain and he was a virtual vegetable most of the time. Immediately on release he entered a Baltimore hospital for brain treatment, and then went on to his Florida home, an estate on Palm Island in Biscayne Bay near Miami, which he had purchased in 1928.
Following his release, he never publicly returned to Chicago. He had become mentally incapable of returning to gangland politics. In 1946, his physician and a Baltimore psychiatrist, after examination, both concluded Al Capone then had the mentality of a 12-year-old child. Capone remained with his wife and immediate family, in a secluded atmosphere, until his death due to a stroke and pneumonia on January 25, 1947.