William “Bill” McCoy   

William “Bill” McCoy and his brother Ben started a motor boat service and boatyard based in Jacksonville and Holly Hill, Fla. in the early 1900s. They built high quality yachts for big names in the area. But, after the business started slowing down, McCoy transformed his boating business into a rum runner operation from the Bahamas to locations all over the Eastern Seaboard.

While the saying “the real McCoy” was popular before McCoy’s birth, people came to know him as The Real McCoy due to his sale of pure, non-watered down liquor and honest dealings.

During the time of McCoy’s coastal reign, plenty was happening in Jacksonville proper. The Acosta Bridge, then called the St. Johns River Bridge, was the Gateway to Florida.  Bootleggers used it to smuggle liquor from Mineral City (Ponte Vedra Beach) and Miami to northern states.      

John Hylser

One particular bootlegger, John Hysler, was called the Whiskey king of Duval County. His ties to Al Capone made his role as a bootlegger important on the First Coast. He was known for smuggling red whiskey from Mineral City.

In September of 1928, prohibition authorities caught wind that Hysler would be running whiskey into downtown Jacksonville, so they camped on the St. Johns River Bridge and waited for him.

The prohibition agents stopped Hysler’s hot roadster at the toll booth, but he attempted to thwart their plans by speeding off. The agents unloaded their .45 caliber automatic weapons into his car, hitting Hysler in the shoulder, chest and neck. He died later that evening from the wounds. Hysler was remembered by Jacksonville residents as a lifeline to alcohol. Over one thousand people showed up to his funeral to honor his memory, and morn his loss.