Web Xtra: Al Capone’s Miami Bootlegger

Few know of Al Capone’s use of pilots to transport illegal booze into Florida. This story is about one of them.

For more on Capone’s South Florida legacy, pick up the July-August issue of Boca Raton.

Flying Ace for Capone

Robert Hanley, 17, was juggling high school at Miami Beach’s St. Patrick Catholic School, flying, and his part-time job at a Miami restaurant when he met the infamous Chicago gangster Al Capone. The year was 1926, the height of Prohibition.

The Chicago mobster asked the young aviator whether he’d be interested in transporting certain “cargo” from the Bahamas back to Miami. Young Hanley jumped at the chance. After lying to his parents, the teen hopped a boat to West End in the Bahamas where, at dusk, he climbed into the cockpit of his plane. Just over an hour later, he arrived in Biscayne Bay where he delivered his first load—26 cases of prohibited whiskey—for which he was paid $300. Occasionally he flew Sundays, returning on Mondays late for school.

On one Sunday delivery, he heard shouts—“Hey! Get outta here!”—then the cargo hatch slammed shut. Someone had blown the whistle on him. Hanley made it into the air, but he was headed toward a Coast Guard cutter. Instead of turning out to sea, he did a 180 and buzzed the vessel. A loud BOOM, excruciating pain, and blood soaked pants soon revealed Hanley had been hit by gunfire.

“I remember praying and feeling groggy like I was going to faint and got down close to the water. That’s all I remember,” wrote Hanley in his memoirs, a thick typewritten document.

Capone’s men found Hanley in a mangrove swamp miles from West End and transported him by speedboat to Capone’s base just off Bimini. There the bullet was removed and his leg patched up. Back in school and on crutches, word that Bob Hanleywas a rumrunner and had been shot resulted in a bolstered reputation.

This harrowing experience should have ended young Hanley’s rum running career. It didn’t. On a subsequent run in a land plane, he was to off-load 115 cases of whiskey at an obscure inland airfield, but government agents were waiting. He abandoned his mission and headed north, a Coast Guard aircraft in hot pursuit.

At dusk, he set down in a field in Georgia. The rough landing and heavy cargo, however, collapsed the landing gear. The resident farmer helped Hanley unload the liquor and remove the plane’s engine and instruments. Hanley then set his plane ablaze after which he phoned Capone—he and the cargo were intact.

The next day, a truck ferried the booze to Capone’s enterprises and a big black car returned Hanley to Miami. Frank “The Enforcer” Nitti Capone’s second in command, told Hanley: “You did such a beautiful job we’d like you to take it easy for a while and lay low.” He handed the teen $2,000 in cash (almost $30,000 today!).

After 80 runs, Hanley retired from rum running. Proceeds from his short-lived but lucrative career paid for a car, his college education and then some. It also gave him the impetus he needed to make flying his career.

His son, Stuart, who is a commercial pilot in south Florida, holds tightly to his father’s memoir that includes his time flying ace for Capone.