From Brooklyn to Palm Island: The Life of Alphonse Gabriel Capone

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He would earn the name Scarface and lead one of the most notorious crime syndicates in history.

By C.J. Oakes / 06.24.2017

Al Capone was born at the end of the 19th Century in Brooklyn in New York City to Italian immigrants. Eventually, he would earn the name Scarface and lead one of the most notorious crime syndicates in history from his base of operations in Chicago, Illinois. Although enormously successful in criminal terms, Capone was captured, sentenced, and served time for tax evasion. He died at the age of 48 at his mansion in Palm Island, Florida.

Rise to Lead Chicago Organized Crime

Al Capone gained fame during the Prohibition era as the co-founder and boss of the Chicago Outfit. His seven-year reign as crime boss ended with his arrest and conviction at the age of 33. Prior to taking charge of the Chicago Organized Crime family, Capone had been a Five Points Gang member. One of his jobs in New York City was a bouncer in organized crime brothels.

Capone in New York City

Al Capone was born in Brooklyn in New York City on January 17, 1899. His parents were Italian immigrants Gabriele Capone (1865 – 1920) and Teresa Capone (née Raiola; 1867 – 1952). The Capone family immigrated to the United States; they first moved from Angri, a town in the Province of Salerno, Italy to Fiume, Austria-Hungary (present day Rijeka, Croatia) in 1893, then to the U.S. shortly after. The Capone’s made their home in Brooklyn, NY where they would raise nine children, Alphonse being the eldest. The family initially resided at 95 Navy Street; when Al was 11, they moved to 38 Garfield Place in Park Slope, Brooklyn.

Al’s father, Gabriele Capone worked at a nearby barber shop at 29 Park Avenue. and his mother was a seamstress.

Brothers and Sisters

  • Vincenzo Capone, who later changed his name to Richard Hart became a Prohibition agent in Homer, Nebraska
  • Raffaele James Capone, AKA Ralph “Bottles” Capone who took charge of Al’s Beverage industry
  • Salvatore “Frank” Capone, who died in a gunfight with Chicago Police
  • Ermina Capone, who died at the age of One
  • Ermino “John” Capone, also called Mimi was spokesman for his older brother, possibly survived until 1994 under the name Martin
  • Umberto “Albert” Capone, largely avoided serious trouble with the law, changed his last name to Rayola in 1942, died 1980
  • Matthew Capone, called “the good one” lived until January 1967
  • Mafalda Capone (who married John J. Maritote), 13 years younger than Al, lived until 1988 and was never directly involved or implicated in any crimes

Frank Capone was killed by police on April 1, 1924. Capone had sent his brother and others to voting stations in support of Republican candidate Joseph Z. Klenha. Their methods included assault and threats of violence with each carrying machine and shotguns. When police arrived to confront Frank, gunfire ensued. Although the situation was controversial, the law enforcement officers were cleared.

For his part, Al spared no expense on his brother’s funeral, having $20,000 worth of flowers placed on a silver-plated casket. For the duration of the funeral, he closed the speakeasies and gambling dens in honor of Frank.

Marriage and Family

Capone married Mae Josephine Coughlin at age 19 on December 30, 1918. She was Irish Catholic and earlier that month had given birth to their son Albert Francis “Sonny” Capone. Capone was under the age of 21, and his parents had to consent in writing to the marriage.

Capone had already become involved with small-time gangs that included the Junior Forty Thieves and the Bowery Boys. He then joined the Brooklyn Rippers and shortly thereafter the powerful Five Points Gang based in Lower Manhattan. At one point, he was employed and mentored by fellow racketeer Frankie Yale, a bartender in a Coney Island dance hall and saloon called the Harvard Inn.

As with any newlywed young father, Al Capone was alert for opportunity. It did not take long for the right one to find him.

Capone Moves His Family to Chicago

At about 20 years of age, Capone left New York for Chicago at the invitation of Johnny Torrio, who was imported by crime boss James “Big Jim” Colosimo as an enforcer. In Chicago, he first worked as a bouncer in a brothel; this was where he contracted syphilis. Timely use of Salvarsan probably could have cured the infection, but he apparently never sought treatment.

In 1923, Capone purchased a small house at 7244 South Prairie Avenue in the Park Manor neighborhood on the city’s south side for US$5,500. In the early years of the decade, Capone’s name began appearing in newspaper sports pages, where he was described as a boxing promoter.

Chicago’s location on Lake Michigan gave access to a vast inland territory, and it was well-served by railroads. Torrio took over Colosimo’s crime empire after Colosimo’s murder on May 11, 1920. Capone was a prime suspect but nothing ever came of it.

Becoming Chicago’s Crime Boss

Johnny Torrio headed what was essentially an Italian organized crime group that was the biggest in the city of Chicago, with Capone as his right-hand man; Capone was both a bodyguard and trusted assistant to Torrio. As head of a criminal syndicate that illegally supplied alcohol—the forerunner of the Outfit— that was politically protected through the Unione Siciliana, Torrio was wary of being drawn into gang wars and tried to negotiate agreements over territory between rival crime groups.

At the height of Prohibition, the only organized crime gang to avoid bloodshed were the Policy Kings. An African American crime group, they agreed to refrain from the trade in alcohol. This wise move kept them out of the ensuing turf wars and off the radar of even Federal law enforcement for the duration of the period.

The smaller, mixed ethnicity North Side Gang led by Dean O’Banion (also known as Dion O’Banion) came under pressure from the Genna brothers, who were allied with Torrio. O’Banion found that, for all Torrio’s pretensions to be a settler of disputes, he was unhelpful with the encroachment of the Gennas into the North Side. In a fateful step, Torrio either arranged for or acquiesced to the murder of O’Banion at the latter’s flower shop in October 1924. This placed Hymie Weiss at the head of the gang, backed by Vincent Drucci and Bugs Moran. Weiss had been a close friend of O’Banion, and the North Siders considered revenge on his killers a priority.

Conflict with the North Side Gang

In January 1925, Capone was ambushed, leaving him shaken, but unhurt. Twelve days later, Torrio was returning from a shopping trip when he was shot several times. After recovering, Torrio decided to retire and handed control to Capone.

A photo of young Al Capone with his mother / Wikimedia Commons

At the age of 26, Al Capone became the new boss of an organization that consisted of illegal breweries and a transportation network that stretched into to Canada and included political and law-enforcement protection. In turn, he could use violence to increase revenue. Refusal by an establishment to purchase liquor from him often resulted in the premises being blown up. As many as 100 people were killed in such bombings during the 1920s.

Capone based himself in Cicero after using bribery and widespread intimidation to take over during elections for the town council. The location made it difficult for the North Siders to target him. Capone’s driver was found tortured and murdered, and there was an attempt on Weiss’s life in the Chicago Loop. On September 20, 1926, the North Side Gang used a ploy outside the Capone headquarters at the Hawthorne Inn, aimed at drawing him to the windows. Gunmen in several cars then opened fire with Thompson submachine guns and shotguns at the windows of the first-floor restaurant. Capone was unhurt and called for a truce, but the negotiations fell through. Three weeks later, Weiss was killed outside the former O’Banion flower shop North Side headquarters. In January 1927, the Hawthorne’s restaurant owner, a friend of Capone’s, was kidnapped and killed by Moran and Drucci.

Using Political Alliances to Gain and Hold Power

As crime boss in Chicago, Capone made friends with those in positions of local authority including many on the police force and in the Mayor’s office including the mayor himself. He was generous in public and came to be viewed as a Robin Hood figure. In a short time, he gained enormous popularity and though he would lose much of it, is ties to the community would shield him from most of the later efforts by law enforcement to obtain evidence against him.

His mutually profitable relationships with Mayor William Hale Thompson and the city’s police made Capone believe his Outfit safe from law enforcement. But it was a short-lived illusion.

The protagonists of Chicago’s politics had long been associated with questionable methods, and even newspaper circulation “wars”, but the need for bootleggers to have protection in city hall introduced a far more serious level of violence and graft.

Home of Al Capone, viewed at an angle from across the street, located at 7244 Prairie Avenue in the Greater Grand Crossing community area of Chicago, Illinois. An automobile is parked along the curb in front of the house. / Wikimedia Commons

Capone is generally seen as having an appreciable effect in bringing about the victories of Republican William Hale Thompson, especially in the 1927 mayoral race when Thompson campaigned for a wide-open town, at one time hinting that he’d reopen illegal saloons. Such a proclamation helped his campaign gain the support of Capone, and he allegedly accepted a contribution of $250,000 from the gangster. In the 1927 mayoral race, Thompson beat William Emmett Dever by a relatively slim margin. Thompson’s powerful Cook County political machine had drawn on the often-parochial Italian community, but this was in tension with his highly successful courting of African Americans.

Capone continued to back Thompson. Voting booths were targeted by Capone’s bomber James Belcastro in the wards where Thompson’s opponents were thought to have support. On the polling day of April 10, 1928, the so-called Pineapple Primary, at least 15 people were killed after more than 60 bombs were thrown at voting stations. The word pineapple referred to the type of grenade used.

Belcastro was also accused of the murder of lawyer Octavius Granady, an African American who challenged Thompson’s candidate for the African American vote. Granady was chased through the streets on polling day by cars of gunmen before being shot dead. Four policemen were among those charged along with Belcastro, but all charges were dropped after key witnesses recanted their statements. An indication of the attitude of local law enforcement to Capone’s organization came in 1931 when Belcastro was wounded in a shooting; police suggested to skeptical journalists that Belcastro was an independent operator.

Increasing Caution

Capone became increasingly security-minded and desirous of getting away from Chicago. As a precaution, he and his entourage would often show up suddenly at one of Chicago’s train depots and buy up an entire Pullman sleeper car on a night train to places like Cleveland, Omaha, Kansas City, Little Rock, or Hot Springs, where they would spend a week in luxury hotel suites under assumed names.

In 1928, Capone paid $40,000 to beer magnate August Busch for a 14-room retreat at 93 Palm Avenue on Palm Island, Florida, in Biscayne Bay between Miami and Miami Beach. However, he never registered any property under his name. He did not even have a bank account, but always used the Western Union for cash delivery, though never more than $1,000 at a time. By 2009, the estate was put on the market for nearly $10 million USD.

In April 1930, Capone was arrested on vagrancy charges when visiting Miami Beach; the governor had ordered sheriffs to run him out of the state. Capone claimed that Miami police had refused him food and water and threatened to arrest his family. He was charged with perjury for making these statements but was acquitted after a three-day trial in July.

In September, a Chicago judge issued a warrant for Capone’s arrest on charges of vagrancy then used the publicity to run against Thompson in the Republican primary.

In February 1931, Capone was tried on a contempt of court charge. In court, Judge James Herbert Wilkerson intervened to reinforce questioning of Capone’s doctor by the prosecutor. Wilkerson sentenced Capone to six months, but he remained free while on an appeal of the contempt conviction.

Still, these minor charges indicated that the winds of change were coming for Capone.

Fall from Grace

Al Capone had grown accustomed to using violence as a means of controlling the illegal trade in alcohol and other vices. The Chicago Police under the direction of the Mayor looked away because the gangster paid for their cooperation. The citizens ignored his acts because he showered them with gifts as if Robin Hood. That all changed on February 14, 1929, when seven men were murdered by gunfire in broad daylight.

The 1929 Saint Valentine’s Day Massacre led to public disquiet about Thompson’s alliance with Capone and was a factor in Anton J. Cermak winning the mayoral election on April 6, 1931.

Valentine’s Day Massacre / Wikimedia Commons

Capone was widely assumed to have been responsible for ordering the 1929 Saint Valentine’s Day Massacre to kill Bugs Moran, the head of the North Side Gang. Moran was the last survivor of the main North Side gunmen; his succession had come about because his similarly aggressive predecessors Vincent Drucci and Hymie Weiss had been killed in the violence that followed the murder of original leader Dean O’Banion.

To monitor their targets’ habits and movements, Capone’s men rented an apartment across from the trucking warehouse and garage at 2122 North Clark Street that served as Moran headquarters. On the morning of Thursday, February 14, 1929, Capone’s lookouts signaled gunmen disguised as police to start a “raid.” The faux police lined the seven victims along a wall without a struggle, then signaled for accomplices with machine guns. It was a slaughter.

Photos of the victims shocked the public and damaged Capone’s reputation and public image in Chicago. Because of the boldness of the murders, influential citizens began to demand that authorities act to stop the gang violence. Newspapers dubbed Capone Public Enemy No. 1.

Within days, Capone received a summons to testify before a Chicago grand jury on violations of the federal Prohibition Law, but he claimed to be too unwell to attend at that time.

Guy Murchie Jr. of the Chicago Daily Tribune would later attribute at least 33 deaths to Al Capone, whether directly or indirectly.

Federal Authorities Close In

Eliot Ness, a new agent for the Federal Bureau of Investigation was selected to lead the fight against prohibition violators in Chicago. Capone was the focus of his investigation. Although every effort was made to connect the crime boss to murder, rackets, and many other criminal acts, no such ties could ever be made. President Herbert Hoover himself wanted Capone stopped and Ness, a former Treasury Agent, devised an ingenious strategy.

An inside, high-resolution picture of Al Capone’s cell as it exists today at Eastern State Penitentiary. / Wikimedia Commons

Unable to tie Al Capone directly to criminal acts, Ness determined that his money had to be coming from somewhere. If Capone could not legitimately account for his assets, they were clearly criminal. More than this, Capone had invented money laundering. He bought several laundries in Chicago to funnel his money through – in dirty, out clean. Ness made the necessary connections in this scheme and brought Capone up on charges of Tax Evasion.

Prosecuted in 1931 for this federal crime, it was a novel strategy during the era. During a highly publicized case, the judge allowed into evidence Capone’s admissions of his income and unpaid taxes during prior failed negotiations to pay the government back taxes owed. Capone was convicted and sentenced to 11 years in federal prison.

After conviction, he replaced his old defense team with experts in tax law and his grounds for appeal were strengthened by a Supreme Court ruling. However, his appeal ultimately failed.

Making the Case against Capone

In May 1929, Capone had been sentenced to a prison term in Philadelphia’s Eastern State Penitentiary; he was convicted within 16 hours of being arrested for carrying a gun during a trip there. A week after his release in March 1930, Capone was listed as the number one “Public Enemy” on the unofficial Chicago Crime Commission’s widely publicized list.

On March 27, 1929, Capone was arrested by FBI agents as he left a Chicago courtroom after testifying to a grand jury that was investigating violations of federal prohibition laws. He was charged with contempt of court for feigning illness to avoid an earlier appearance.

Although arrested many times and convicted on minor charges, none of the major charges sought by authorities found traction. So, Federal law enforcement officers under the direction of Ness took another approach: They opened an IRS investigation of Al Capone. The Internal Revenue Service (IRS) would accomplish what criminal investigators could not.


In 1927, the Supreme Court ruled that illegally earned income was subject to income tax. Justice Oliver Wendell Holmes Jr. rejected the argument that the Fifth Amendment protected criminals from reporting illegal income. The IRS special investigation unit chose Frank J. Wilson to investigate Capone, with the focus on his spending.

The key to Capone’s conviction on tax charges was proving his income, and the most valuable evidence in that regard originated in his offer to pay tax. Ralph, his brother and a gangster in his own right, was tried for tax evasion in 1930. Ralph spent the next three years in prison after being convicted in a two-week trial over which Wilkerson presided.

Al Capone Portrait / Wikimedia Commons

Capone ordered his lawyer to regularize his tax position. Crucially, during the ultimately abortive negotiations that followed, his lawyer stated that Capone was willing to pay tax on income for various years, admitting income of $100,000 for 1928 and 1929, for instance. Hence, without any investigation, the government had been given a letter from a lawyer acting for Capone conceding his large taxable income for certain years.

In 1931, Capone was charged with income tax evasion, as well as with various violations of the Volstead Act (Prohibition) at the Chicago Federal Building in the courtroom of Judge James Herbert Wilkerson. U. S. Attorney George E. Q. Johnson agreed to a deal that he hoped might result in the judge giving Capone a couple of years, but Judge Wilkerson had been aware of the deal all along and refused to allow Capone to plead guilty for a reduced sentence.

On the second day of the trial, Judge Wilkerson overruled objections that a lawyer could not confess for his client, saying that anyone making a statement to the government did so at his own risk. Wilkerson deemed that the 1930 letter to federal authorities could be admitted into evidence from a lawyer acting for Capone.

Much was later made of other evidence, such as witnesses and ledgers, but these strongly implied Capone’s control rather than stating it. The ledgers were inadmissible on grounds of statute of limitations, but Capone’s lawyers incompetently failed to make the necessary timely objection; they also ran a basically irrelevant defense of gambling losses.

Judge Wilkerson allowed Capone’s spending to be presented at very great length. There was no doubt that Capone spent vast sums but, legally speaking, the case against him centered on the size of his income.

Capone was convicted on October 17 and was sentenced a week later to eleven years in federal prison, fined $50,000 plus $7,692 for court costs, and was held liable for $215,000 plus interest due on his back taxes. The contempt of court sentence was served concurrently.

Appeal and Imprisonment

New lawyers hired to represent Capone were Washington-based tax experts. They filed a writ of habeas corpus based on a Supreme Court ruling that tax evasion was not fraud, which apparently meant that Capone had been convicted on charges relating to years that were outside the time limit for prosecution. However, a judge interpreted the law so that the time that Capone had spent in Miami was subtracted from the age of the offenses, thereby denying the appeal of both Capone’s conviction and sentence.

Unemployed men queued outside a depression soup kitchen opened in Chicago by Al Capone, 02-1931 – NARA – 541927 / Wikimedia Commons

Capone was sent to Atlanta U.S. Penitentiary in May 1932, aged 33. Upon his arrival at Atlanta, the 250-pound Capone was officially diagnosed with syphilis and gonorrhea. He was also suffering from withdrawal symptoms related to cocaine addiction, the use of which had perforated his septum. Capone was competent at his prison job of stitching soles on shoes for eight hours a day, but his letters were barely coherent.

As an inmate, Capone was considered weak and was so out of his depth dealing with fellow inmates that his cellmate, seasoned convict Red Rudinsky, feared that Capone would have a breakdown. Rudinsky was formerly a small-time criminal associated with the Capone gang and found himself becoming a protector for Capone. The conspicuous protection by Rudinsky and other prisoners drew accusations from less friendly inmates and fueled suspicion that Capone was receiving special treatment. No solid evidence ever emerged, but it formed part of the rationale for moving Capone to the recently opened Alcatraz Federal Penitentiary off the coast of San Francisco.

At Alcatraz, Capone’s decline became increasingly evident as neurosyphilis progressively eroded his mental faculties. On June 23, 1936, Capone was stabbed and superficially wounded by James C. Lucas. He spent the last year of his sentence in the prison hospital, confused and disoriented. Capone completed his term in Alcatraz on January 6, 1939, and was transferred to the Federal Correctional Institution at Terminal Island in California to serve out his sentence for contempt of court. He was paroled on November 16, 1939.

Release from Prison and Death

Capone was already showing signs of syphilitic dementia early in his sentence, and he became increasingly debilitated before being released after eight years. He spent another eight years of freedom and labored retirement in Miami before his final arrest.

The location of the Miami home of Al Capone where the infamous criminal finally met his end, his final arrest being cardiac. / Google Maps

After Capone was released from prison, he was referred to Johns Hopkins Hospital in Baltimore for the treatment of paresis (caused by late-stage syphilis). Hopkins refused to admit him based solely on his reputation, but Union Memorial Hospital accepted him. Capone was grateful for the compassionate care that he received and donated two Japanese weeping cherry trees to Union Memorial Hospital in 1939. A very sickly Capone left Baltimore on March 20, 1940, after a few weeks inpatient and a few weeks outpatient, for Palm Island, Florida.

In 1946, his physician and a Baltimore psychiatrist performed examinations and concluded that Capone had the mentality of a 12-year-old child. The former crime boss spent the last years of his life at his mansion in Palm Island, Florida. On January 21, 1947, Capone had a stroke. He regained consciousness and started to improve, but contracted pneumonia. Then his final arrest came; he suffered a cardiac arrest on January 22 and by January 25 the gangster died, surrounded by his family.

Al Capone was buried аt Mount Carmel Cemetery in Hillside, Illinois.

The Vain Nature of Capone

On one occasion, Capone inadvertently insulted a woman while working the door at a Brooklyn night club and was slashed by her brother Frank Gallucio. The wounds led to the nickname that Capone loathed: Scarface. Yale insisted that Capone apologizes to Gallucio; the two must have made amends because Capone later hired Gallucio as his bodyguard. In keeping with his vain nature, when photographed, Capone hid the scarred left side of his face saying that the injuries were war wounds.

Further demonstrating his vain nature Capone was called “Snorky” by his closest friends because his clothing was impeccable always.

Capone indulged in custom suits, cigars, gourmet food, and drink (his preferred liquor was Templeton Rye from Iowa. A womanizer, he was particularly known for his flamboyant and costly jewelry. His favorite responses to questions about his activities were: “I am just a businessman, giving the people what they want” and “All I do is satisfy a public demand.” Capone had become a national celebrity and talking point.

Throughout his criminal career, Capone seemed to crave attention. When he appeared at ball games, spectators cheered. When he later bought a Mansion in Miami, he was treated as a celebrity in the city. He made donations to various charities and was viewed by many to be a modern-day Robin Hood.

Perhaps this was the driving force behind Capone’s entry and rise in the criminal world. Although many claim that crime does not pay, in many ways it does. For those who seek adoration and attention, crime can provide a rapid means to those ends. Perhaps this point is best made by another Scarface, the one played by Al Pachino in the movie of the same name. The character said,

“First you get the money, then you get the power, then you get the girls.”


One could surmise that Capone’s craving for attention was the result of not getting enough attention at home. The oldest child of immigrant working parents, he likely watched his father struggle to provide for his family. The tutoring of a successful criminal such as Johnny Torrio would have surely made an impact. Working in brothels would have taught the young man that women can be had for the right price. Then, being given the reigns of enormous power at an early age would have solidified these lessons. Really, for Capone not to have become such an infamous criminal would have been odd.


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