Anna Maria Island, August 26, 1987

The Cracker meets some bootleggers

By Gib Bergquist

In a recent column, the Cracker told about vacationing on Indian Rocks Island as a boy in the late 1920s and 1930s when that Island was sparsely populated.

The company for whom the Cracker’s dad worked, in Pierce, built eight vacation beach cottages for use by its employees as well as a fishing pier stretching 300 feet out into the Gulf. As soon as school was out, the family would head for the beach and stay for most of the summer. Dad would be there for his regular vacation and then join us on weekends for the remainder of our stay.

This was also true of the seven other families who were vacationing at the same time. It therefore frequently happened that, during the week, there were no dads around — just moms and a passel of bronzed kids. On one such occasion during the summer of 1932, when Prohibition was still in effect, we brothers noticed a fairly large ship anchored a half-mile or so off the end of our pier.

When the families gathered on the pier to watch the sun sink into the Gulf of Mexico that same evening, we saw that the ship was still there. About the same time, a big black car drove up to the pier parking area and two tough-looking armed men emerged.

The two men walked out on the pier and very sternly ordered my mother and the other mothers present to vacate the pier immediately. Our moms also were instructed to remain in the cottages until morning. The mothers had no choice but to comply, but my gutsy mom did permit us boys to climb to the top of a water tower which was set back several hundred feet from the beach in the cottage area.

From our vantage point atop the tower platform, the Cracker, at the age of eight, was able to peek around the tank and get a bird’s eye view of a major crime in progress.

The ship approached the pier and tied up at about the same time as a convoy of several trucks arrived. In the twilight, we saw men unloading wooden boxes from the ship. The boxes were carried off the dock and loaded into the waiting trucks. After the ship was unloaded, it shoved off into the night. We excitedly watched as the headlights of the convoy traced a pattern of light up the oyster shell road toward the bridge and then disappeared.

Obviously, what we had witnessed was a “rumrunner” ship unloading its cargo of contraband booze from Cuba or some other spirit-producing country. Much the same thing still goes on in various rural Florida locations to this very day — except now it’s cocaine and marijuana.

Adult comment at the time was that local law enforcement officers “had to be in the know,” because no straight-thinking bootlegger would have so blatantly off-loaded his cargo on an Island that exited over only one bridge — the chance of being bottled up was just too great. This tainted the Cracker’s respect of local law enforcement in Florida during the Prohibition Era. My knowledge of lawmen up to that point was limited to our town marshal, “Uncle Joe” Overstreet, whom I admired and loved.

The Cracker’s decision to devote his life to law enforcement was not fomented on the spot, but after the frightening experience of seeing at an early age our laws broken and our freedom curtailed, the incident certainly left a deep and lasting impression.

While on the subject of the Prohibition Era, everyone will agree that Al Capone was the best-known hood of that time. Largely because of ol’ Scarface’s notoriety, our Italian friends may have unjustly borne the brunt of being the ethnic group most closely associated with organized crime in America during Prohibition.

In their defense, the Cracker has compiled a list of the best-known organized crime hoodlums of 1930 and lists them as follows: Al Capone, Vincent “Mad Dog” Coll, Owney Madden, William Vincent Dwyer, “Lucky” Luciano, “Dutch” Schultz, “Legs” Diamond, George “Bugs” Moran and Hymie Weiss.

You be the judge.


From Cracker's Crumbs, 1995 Gib Bergquist


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