In the beginning, the public glamorized Capone’s activities and identified with him as a modern day Robin Hood. It wasn’t long, however, before public opinion started turning against him when it was believed that he had ordered the death of a famed local public prosecutor named Billy McSwiggin. The young prosecutor had earlier tried to pin the violent murder of a rival gang member on Capone. Although many argued against Al’s involvement in McSwiggin’s death, there was a great outcry over gangland violence at the time, and public sentiment went against Capone.

Capone quickly went into hiding, fearing he would be tried for McSwiggin’s murder. He remained out of sight for nearly three months, and then after realizing he couldn’t live the remainder of his life underground, he negotiated his own surrender to the Chicago Police. The authorities eventually recognized that they lacked sufficient evidence to bring Capone to trial, and though the decision proved very unpopular with the public, he was eventually set free. The community was outraged and law officials were left publicly embarrassed by the incident. “Big Al” had become one of the most powerful crime czars in Chicago. It was said that Capone was now larger than life, and more powerful than the Mayor himself.

By 1929 Capone’s personal empire was worth over $62 million and he was ready to wage war on his most prominent bootlegging rival, George “Bugs” Moran. Bugs was another of Chicago’s principal gangsters. He was known to talk openly against Capone and he maintained an attitude of spiteful arrogance that was said to anger Capone so much that Moran became one of Al’s regular topics of discussion. It was rumored that Capone gave orders to take Bugs down by assassinating his gang members from the bottom up, not stopping until they reached Bugs himself.

Capone was now living lavishly on Palm Island in Miami Beach, Florida, and he drafted one of his top associates Jack “Machine Gun” McGurn to mastermind the hit. McGurn had one of his bootleggers lure members of the Moran gang into a garage to buy liquor at an unreasonably cheap price. The deal was made and the delivery was scheduled to take place on St. Valentine’s Day, 1929. McGurn and his men awaited their victims in stolen police uniforms. When the rival mobsters arrived, McGurn’s gang pretended to be policemen making a bust and ordered all of Moran’s men to stand facing the wall. Thinking that they had just been caught by the police, seven members of the Moran gang turned to the wall awaiting arrest. McGurn and his men then opened fire with machine guns, killing all of the gangsters. Bugs himself had seen the police car before stopping his vehicle and thinking that it was a raid, he fled the scene. Capone was credited with what would be one of the most famous mass murders in American history, the “St. Valentine’s Day Massacre.”

A waterfront view of Al Capone’s Palm Beach Mansion.

A mug shot of Capone taken in Miami, Florida.

The scene of the brutal St. Valentine’s Day Massacre.

Seven members of George “Bugs” Moran’s gang were lined up against a wall and mowed down by two machine gunners impersonating police officers.

A diagram showing how the massacre unfolded at the S.M.C. Cartage Company at 2122 North Clark Street in Chicago. Chicago Gangster Frank Gusenberg (left) suffered twenty-two bullet wounds and later died at the hospital. Jack “Machine Gun” McGurn (right) was one of Capone’s hit men and speculated as the mastermind of the massacre.

Law enforcement officials recreate the massacre at the North Clark Street property.

The massacre received national attention and Capone was glamorized in books and newspapers across the country. Capone was now a high-class, family-oriented and self-made gangster-millionaire, who had everyone’s full attention. Many local politicians began complaining about Capone and his self-proclaimed political stature. However the publicity surrounding Capone ultimately backfired, by attracting the attention of President Herbert Hoover. Hoover had just started his presidential term and as one of his first moves, he demanded that Capone be brought to justice. Hoover pressured Secretary of the Treasury Andrew Mellon to spearhead the government’s battle against Capone. Mellon collected damning evidence which exposed his gang affiliations, bootlegging, prostitution rings and flagrant evasion of taxes.

Al Capone in 1931, at a baseball game in Chicago. Note the bodyguard behind Capone, who is reaching for his handgun as the peanut vendor approaches. Frank “The Enforcer” Nitti (known as Capone’s master killer) is seen seated next to Capone, along with his son.

It would take nearly five years of an intensive undercover operation before Capone was finally convicted. Then on October 17, 1931, Alphonse Capone was sentenced to eleven years in prison and $50,000 in fines, and was forced to pay court fees totaling over $30,000. The judge refused to allow Capone to be released on bail and the gangster remained confined at the Cook County Jail until arrangements were made for his transfer to Atlanta. On May 4, 1932 Capone began serving out his federal prison sentence at the Atlanta Federal Penitentiary. Capone flaunted his power even in prison, and quickly secured the ability to dictate his own privileges. He was given unlimited access to the Warden and was said to maintain large reserves of cash hidden in his cell, often generously “tipping” guards who would assist him by yielding to special requests. His time spent at Atlanta would not be as plush as his confinement at Cook, but he still found means to manipulate the system.

Capone boarding the prison train for Atlanta Federal Penitentiary on May 3, 1932. He is seen here under heavy guard with federal agents and U.S. Marshal Henry Laubenheimer as his personal escort.

Capone’s criminal history from his inmate file.

A request by Capone to use the prison recreation yard at Atlanta State Penitentiary.

A contemporary photograph of Capone’s uniquely furnished cell at Eastern State Penitentiary. Before his arrival at Alcatraz, Capone had managed to set the terms of his own privileges while incarcerated at other prisons.

Before his transfer to Alcatraz, Capone had already become a master at controlling his environment at the federal penitentiary in Atlanta. Despite strict rulings from the courts, Capone was always able to persuade his guards to bend rules and accommodate his unique requests, often setting his own terms of confinement. It was rumored that he had convinced many of the guards to be on his payroll and his cell boasted expensive furnishings including personal bedding, and many other amenities that were not extended to other inmates serving lesser sentences. His cell was carpeted and he had a radio around which many of the guards would sit with him, conversing and listening to their favorite serials. His friends and family maintained residence in a nearby hotel, and each day he was flooded with visitors who were personally escorted to his cell.