Prohibition was in effect for over a year and a half when on the evening of Aug. 2, 1921, Sheriff Frank Tippins observed a boat plying between Sanibel and Punta Rassa. On a hunch, he approached the vessel and boarded. Spotting demijohns of liquor, Tippins bargained with the captain and purchased some Cuban rum for $25, then placed him under arrest. “Captain and Crew of Cuban Smack Caught in Big Liquor Raid” was the headline in the morning paper.

Sensational Raid

In what the paper deemed “a sensational raid,” Sheriff Tippins and his son, Deputy Sheriff Frank Tippins, Jr., “arrested the captain and the four members of the crew of a Cuban smack, confiscated three demijohns of liquor and the smack itself, and landed the five men in jail.”

The Tippins had been en route to Sanibel to make an arrest when their suspicions were aroused seeing a Spanish fishing smack. As the elder Tippins began to apprehend the captain, “he became crazed and attacked the sheriff, fighting like a mad man,” reported the paper. “It required a physical argument, in which Sheriff Tippins came out victorious, to convince the captain that he was up against the real thing.”

During the scuffle, Tippins hollered for his son to shoot, but the younger Tippins refrained for fear of injuring his father.

Human life is as nothing to them

None of the crew spoke English, and the reporter noted their outward show. He wrote he was “struck with the pirate appearance of the crew, barefoot, two of the crew having heads bandaged up and one with a badly discolored eye. They are of the same mold and cast as the pirates in days of old, and human life is as nothing to them.”

The following morning, armed with a search warrant, the sheriff returned to the boat and discovered two more demijohns of liquor and a fourth crew member. He immediately arrested the deckhand and confiscated the remaining liquor.

Legal Matters & Years of Trying

After going through legal procedures in the circuit court, the vessel was to be sold and the money invested in the Fines and Forfeiture Fund used for the prosecution of criminal matters.

The captain of the smack, Antonio Lopez, was found guilty and fined $500 ($6,500 in 2014) for “attempting to bring liquor into the county.” Crew members were fined the same amount.

Three weeks later, Judge George W. Whitehurst released the smack back to the company that owned it. The president of the company convinced the judge that “the captain had only four demijohns of rum aboard and this without the knowledge or consent of the owners.”

Boarding smacks and trying to break up rum runners was not new to Tippins. For several years he attempted to collect evidence and arrest runners, including one time posing as a fisherman offering to trade mullet for Cuban rum, which was met with no success.

Inspections Causing Troubles

An article that appeared on the front page of the paper alongside the news of the Cuban smack being released was, “'Booze Ships’ Stories Cause Many Troubles For Tarry Old Salts.” It reported how the “fisher folk [are] disturbed by ceaseless activity of the rum sleuths,” and all the “official and unofficial” inspections taking place.

Other fishermen said as soon as you drop a hook in the water they whisper, “You’re a rum runner.”

By the time prohibition ended in 1933, Tippins had become a U. S. Marshall and fishermen were again enjoying their trade without any hassle from law enforcement.

About the author

T.M. Jacobs, authorT.M. Jacobs is a member of the Board of Directors of the Southwest Florida Historical Society, member of the Corporate Board of the Gulf CoastWriters Assoc. and president owner of Jacobs Writing Consultants in Fort Myers. A student of the American Revolution, he is the author of several historical works, including the recently published Almost Home: The 1864 Diary of Sergeant Samuel E. Grosvenor. The book is available at and has been featured in both the Santiva Chronicle and on CSPAN2's Book TV.