Gangsters in Paradise: Miami’s History with the Mafia

Palm Island is a narrow, man-made island located in Biscayne Bay sitting between Miami and Miami Beach. 93 Palm Island was originally built in 1922 as an investment property by Clarence M. Busch, a member of Anheuser-Busch brewing family that was later sold to an insurance broker. The two-story white mansion had fourteen rooms and a view of Biscayne Bay. Capone paid $40,000 for the mansion and closed on the property in March 1928. He immediately made improvements and renovations including adding an enormously large pool with a salt and fresh water filtration system. Capone spent over $100,000 on additions to his new purchased residence.

Even in Miami, Capone plotted to kill those who were his enemies and Frankie Yale, A Brooklyn crime boss was no exception. Yale had double crossed Capone hijacking some of trucks carrying whiskey through Long Island. Yale felt slighted by Capone for not supporting Joe Aiello’s bid for union president.

In July 1928, Capone’s hit squad killed Frankie Yale in New York City; however, they left one of the firearms used in the murder in a vehicle the crew abandoned. The automatic pistol was traced back to Parker Henderson an associate of Capone in Miami. Henderson confessed to authorities that he had purchased twelve firearms at Capone’s request. Henderson, the manager of the Ponce de Leon hotel near Biscayne Boulevard purchased the twelve firearms from a pawn broker and left them in empty rooms of the hotel as requested by Capone. Authorities later questioned Capone on his knowledge of this murder. This set off numerous revenge killings against Capone’s associates like Tony Lombardo, a handpicked president of the Unione Siciliana by Big Al.

Some residents resented having Capone in South Florida while others embraced him. Capone had a variety of business interests in Miami including in gambling and drinking establishments like the Palm Island Club, the Floridian Hotel gambling room in Miami Beach and dog racing near South Beach. The Miami Beach Kennel Club opened in January 1929 and the owner had an illegal gambling house on the corner of Ocean Drive and Biscayne Street which Capone later involved himself with.

On February 14th, 1929, known as the Saint Valentine’s Day massacre, Big Al had an air tight alibi during the massacre in Chicago since Capone was meeting with the Dade County Solicitor and assistant district attorney from New York at the downtown courthouse in Miami. It is believed Capone gave the order for his gang to kill rival gang members pertaining to George “Bugs” Moran. The assailants dressed as police officers, rounded up seven men and shot them while they were facing a back wall with .45 caliber Thompson “Tommy” machineguns and then drove away. Bugs Moran was running late and missed being included in the ambush. Moran later commented about the massacre of his crew that only Al Caponekills in this manner.

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Due to public pressure and the label of being Public Enemy #1, authorities served Capone a subpoena to appear in Chicago concerning Prohibition violations and was later cited for contempt of court for postponing his appearance.

In May 1929, Capone and an associated were arrested outside a Philadelphia theatre for carrying concealed firearms on them. Both men plead guilty and were sentenced to one year incarceration in Pennsylvania. This was the first time Al Capone had ever been incarcerated in a state prison. He was released ten months later and was on the cover of Time Magazine heightening law enforcement’s attention. Chicago and Miami made it clear they did not want Capone or his gang back in town. The Florida Governor at the time even banned Capone from entering the state of Florida and would be escorted to the state line if he entered.

On March 20th, 1930, local authorities raided Capone’s Palm Island home looking for a fugitive from Ohio. Capone had not yet returned to South Florida and the fugitive was not there. A few of Capone’s family members and friends were arrested on vagrancy charges and possession of illegal alcohol.

Eventually, Capone returned to his Miami Beach home after hiring a pair of young attorneys who filed federal lawsuits against state and local officials. Capone’s attorneys won an injunction against Florida law enforcement from unlawfully seizing, arresting, kidnapping and abusing Capone.

Regardless of the injunction against them, local authorities continued to arrest Capone when seen in South Florida. Big Al responded with another lawsuit this one was aimed at the mayor, commissioner and others in Miami who were conspiring to falsely imprison him. The judge on the case made it clear that this behavior would stop or other public officials would go to jail.

In October 1931, Al Capone was convicted of federal income tax evasion in Chicago, Illinois and was sentenced to ten years in federal prison. After allegations that Capone was receiving special treatment in the Atlanta Federal Penitentiary, the Attorney General at the time had Capone transferred to Alcatraz Island known as “The Rock.” It was considered unescapable since it was surrounded by rough cold waters and sharks in San Francisco Bay. During his time at Alcatraz, Capone had syphilis and this condition deteriorated spending his time in the prison hospital under treatment. In November 1939, Capone was released from prison and went to Baltimore to be treated for his illness.

Capone returned to Miami Beach after losing his illegal income in tax liens, court costs, and attorney fees leaving him his residence on Palm Island. In January 1947, died from a cardiac arrest after years of suffering from the symptoms of syphilis. According to doctors, Capone had the mental capacity of a twelve-year-old. His body was buried on Chicago’s South Side at Mount Olivet Cemetery. His wife sold the mansion in the early fifties to a Cleveland Real Estate broker for $64,000.

On February 15th, 1933, president-elect Franklin Delano Roosevelt (FDR) returned from a fishing trip in the Bahamas and was passing through Miami where he planned on giving a short speech. FDR arrived at Biscayne Park after 9pm and gave a one-minute speech at Biscayne Bay Park where he met with Chicago Mayor Anton Cermak. After the speech, Cermak enter Roosevelt’s vehicle for an informal discussion about Chicago’s future economic plans. As the mayor was exiting the vehicle, shots were fired by lone gunmen later identified as Giuseppe Zangara, an Italian immigrant who shot five rounds with an Iver Johnson .32 caliber revolver. Zangara was short in statue and stood on an unstable folding chair while he fired over the shoulder of a female watching FDR. Zangara fired the first shot and his arm was grabbed by onlookers while he fired four more wild shots striking five people including the Chicago mayor. President-elect Roosevelt was not hit by the assassin and cradled the seriously wounded Cermak in his arms as they were driven to Jackson Memorial hospital. Cermak died nineteen days later from his wounds and before he died allegedly told FDR, “I’m glad it was me, not you.”

Zangara plead guilty to murder and was sentenced to death in Miami by the Circuit Court Judge by electrocution at Raiford, Florida. After ten days on death row, he was executed on March 20th, 1933 by the electric chair known as “Old Sparky”. His last words were “Viva Italia! Goodbye to all poor people everywhere! Push the button! Go ahead, push the button!”

There are numerous theories that Zangara’s true target was actually Mayor Cermak who was hired by the Chicago Outfit to kill him in retaliation for the mayor’s alleged attempt to have Frank Nitti killed by the Chicago Police Department during a raid in his office. Nitti was head of the Chicago Outfit at the time since Capone was incarcerated for tax evasion and the mayor wanted to cripple the Outfit.

A plaque honoring the late mayor still lies in Miami at the scene of the murder at Bayfront Park with the words “I’m glad it was me instead of you” allegedly said by Cermak to president-elect Roosevelt after the shooting.

Mafia crime figures and professional boxing have a long history going back to the late 19th century in the United States. One man in particular named Frankie Carbo was the mob’s so-called commissioner in professional boxing starting in the 1940s. Carbo was an Italian immigrant from Sicily to New York and was in and out of prison starting at an early age. During the early 1930s, he began working for Murder, Inc. hired assassins for the National Crime Syndicate. Carbo was allegedly involved in high profile murders of bootleggers like Mikey Duffy in Atlantic City, Harry Greenberg in California, Bugsy Siegel in Beverly Hills and other mobsters.

During the 1940s, Carbo became a boxing promoter with others knowns as “The Combination” since they were able to fix high-profile boxing bouts. In the late fifties, Carbo and his partner Blinky Palermo owned a majority interest in Sonny Liston’s contract who was a heavyweight fighter and later champion. Around this same time, he was convicted and sentenced to Riker’s Island in New York City for illegally managing boxers without a license. After his release from Riker’s Island, Carbo was subpoenaed to testify before U.S. Senate investigating committee and took the fifth 25 times in order not to incriminate himself.

Former champion Carmen Basilio testified before a Senate Judiciary Committee on Antitrust and Monopoly and provided evidence against Carbo, Palermo and other known mafia members. He testified that his managers had to pay off organized crime in order to have his title shots.

In 1961, Carbo and Palermo were charged with conspiracy and extortion against the National Boxing Association welterweight champion Don Jordon. The attorney General at the time Robert Kennedy served as federal prosecutor on the three-month trial. Both were convicted and Carbo was sentenced to twenty-five years to Alcatraz Island near San Francisco, California. Due to his poor health, Carbo would be released early and died in Miami Beach in November 1976.

On February 25th, 1964, Miami Beach Convention Hall hosted the world heavyweight championship title between reigning champion Sonny Liston and Cassius Clay who later changed his name to Mohammad Ali. Liston had twice beaten former champion Floyd Patterson by first round knockout and was considered by many as one of the best heavyweight boxers of all time. Liston’s ties with organized crime were well known and documented and gave the sport a bad reputation for fight fixing. Clay, twenty-two years old had great hands and foot speed but was knocked out earlier in his career to a journeyman named Sonny Banks. Many saw this fight as a David vs Goliath with Clay having zero chance of winning.

However, Liston was nursing a shoulder injury which severely impacted his training for the upcoming fight and many believed he was years older than what was reported possibly as old as forty. Clay upset the champ with Liston quitting the fight before the start of the seventh round. He cited his should injury with doctors confirming a torn tendon in his left shoulder.

After the fight, there were numerous allegations of fight-fixing especially with the way the fight ended and the odd makers favoring Liston 8–1. After a month-long investigation, authorities concluded there was no evidence of a fix. However, their rematch fight would be more controversial then the first one.

Over a year later, the rematch occurred in Lewiston, Maine becoming one of the most controversial boxing bouts in the history of the sport. This time Clay now known as Muhammad Ali knocked out Liston in the first round of the bout with a quick punch that the audience and reporters did not see questioning Liston’s motives once again. Ali was also heard yelling at Liston, “Get up and fight, sucker!” “Nobody will believe this!” Many spectators were yelling “Fix!” and calling Ali’s knockout blow a “phantom punch.” There are many theories behind the fight including that Liston was forced to take a dive by the mob or he betted against himself to pay off debts he owed the mafia. At the end, it was never was never proven that Liston fixed the fight; however, many saw Liston’s actions as clear indicator of thrown fight by a former champion while seeing Ali’s reaction not believing his punch was strong enough to knock him out. This fight solidified Ali as a world champion while ruining Sonny Liston’s career and reputation.

The legalization of alcohol and gambling all over the United States ended their profitable rackets including in Cuba where their hotels and casinos were nationalized. South Florida played a pivotal role with the mafia and other crime syndicates. Miami will always be tied to the most infamous gangsters in history and their stories will live on for generations.

Interested in learning about the alleged connections between the CIA and the Mafia? Read our in-depth article to explore the historical claims, key events, and the stories behind one of history’s most debated collaborations. Read the full article here: connections between the CIA and the Mafia?