By Marcy Shortuse
History:
THE
SHADIER
SIDE
OF PARADISE
Drug smugglers and bootleggers
of Gasparilla Island
Paradise is a term you can interpret in
a number of ways. For most people
who visit the Gulf Coast of Florida, it
brings to mind the turquoise waters that
can be found in the calm months of winter,
temperate beach visits and endless fi shing
trips. After all, the Gulf of Mexico offers a
rare bounty of fi sh that is known far and
wide; it is a true sportsman’s paradise. But
there are other reasons people choose to
frequent the barrier islands along the Gulf,
reasons that are not quite as wholesome
and pure.
For centuries, the less-inhabited side of
Florida has been a paradise for rumrunners,
bootleggers and drug smugglers. Dense
swamps that are almost impossible for
the common man to traverse became
easy hideouts for a Floridian who grew up
here and knew the way through, and the
mangroves along the coast still provide
hidden inlets and outlets that run for miles
… if you know your way around. It’s very
easy to believe that hundreds of years
ago pirates could have, in fact, made our
coastline their hiding spot for treasure, and
for refuge in general.
While Cuban “smacks” (small sailing ships
that ran from Cuba to destinations in Florida
– including Boca Grande that carried rum
that hadn’t been taxed), were prevalent
many, many years earlier. In the Roaring
20s the Volstead Act (Prohibition) put an
end to casual drinking. This was a popular
pastime for many of America’s wealthiest
population, some of whom frequented
homes in Boca Grande and had little else to
do while at their vacation homes. That was
why bootlegging became a very lucrative
industry, especially for the fi shermen of the
area who already had seaworthy boats but
preferred to make a little more than pennies
per pound from fi sh.
In a May 2020 article in the Palm Beach
Post, journalist Eliot Kleinberg wrote,
“Perhaps nowhere did Prohibition fail so
68 GASPARILLA MAGAZINE • January/February • 2021