John "Caribbean Jack" Gilbert


1903 - 1941

From January 29th, 1920 to March 23rd, 1933, the Volstead Act, better known as the 18th Amendment, prohibited citizens from legally consuming alcoholic beverages in the 48 United States. The distillation and consumption of alcoholic beverages in surrounding countries such as Canada, Mexico, and the Caribbean, however, was legal and booming. John "Jack" Gilbert saw an opportunity and, as he had done his entire life, jumped on-board with all his passion and determination.
Jack, an experienced mariner, began "running" rum from the nearby Bahamian waters to Florida's east coast. From ports in Miami all the way north to Jacksonville, Jack's cargo was transferred to bootleggers who in turn carried the contraband to speakeasy's all along the eastern seaboard and eventually into Chicago's famed Four Deuces. As the Coast Guard pressure increased, Jack and other Runners incorporated go-fast mahogany Garwood and Hacker boats to "run" the rum from the 3-mile international watermark into Florida ports. As Congress increased the "Rum Line" to 12 miles, Jack stayed one step ahead of the law in his now thriving business by switching from sea to air to transport the spirits in newly purchased S-29 Sikorsky Seaplanes. On one particularly turbulent butt-kicking ride, Jack uttered his now-famous "Time Flies when you're having Rum."