Today, I am going to write about a man who spent time in the Florida Keys in the ’30s. He had a reputation as a fighter, was married multiple times, and was also a successful writer.
Those few details may conjure up the image of Ernest Hemingway, and if I were talking about the 1930s, Hemingway would undoubtedly be the man in question. However, I am not writing about the 1930s and referencing one of Key West’s favorite characters — whose footsteps still echo through the island’s streets. The man I’m writing about arrived nearly 100 years earlier, and his name was Edward Zane Carroll Judson.
He was born in Harpersfield, New York, on March 20, 1821. His father was a teacher, writer and a lawyer who wanted his son to become a lawyer, too. When Edward was 12 years old, he and his father had a horrendous fight, and the boy was struck. The blow drove him to run away from home, jump on a ship and become a working sailor on a West Indian schooner shipping fruit.
At 17, he saved the lives of several people involved in a boating accident in New York’s East River. As a reward for his brave actions, President Van Buren appointed him a midshipman in the U.S. Navy. His first orders were to report to Commodore Ridgley of the West Indian Squadron.
One of the things that defined the life of Edward Zane Carroll Judson is that he was a fighter. A popular story about him is that he once challenged 13 of his fellow sailors to a fight. As the tale unfolds, Judson fought seven of them, wounded four and left the affair uninjured. He would not always be so lucky.
While serving in the Navy during the second escalation of the Seminole War (1835-1842), he was assigned to three ships that sailed in the waters surrounding the Florida Keys: Constitution, Flirt, and Ostego. Two of those ships, Flirt and Ostego, were familiar with Indian Key as the small island just offshore of the Matecumbe Keys became a part of Fort Paulding, a base of military operations in the Keys. The island was the site of the southernmost attack during the war.
The Navy spent about $12,000 building three red-bricked cisterns, barracks and a makeshift hospital tent in the weeks following the Aug. 7, 1840 attack. Midshipman Judson would have likely been on Indian Key from time to time and met the island’s most colorful character, Jacob Housman. After resigning from the Navy on June 8, 1842, Judson began writing for a living and penned stories about his time in Florida, Housman, and the Indian Key attack.
He became one of the most successful writers of the 19th century. However, Judson was not the name appearing on the bulk of his work. He is best remembered by his nom de plume Ned Buntline. A contemporary of Mark Twain, the nom de plume of Samuel Clemens, Buntline wrote as many as 400 dime novels, inexpensive melodramatic adventures published in paperback between the 1850s and 1920s.
In the 1860s, he was said to have earned $20,000 per year – about $400,000 In 2024 dollars. One of his most popular stories chronicled the exploits of a buffalo scout Buntline met circa 1869. The scout’s name was William F. Cody. Buntline called him Buffalo Bill and serialized his story, but also wrote a play that starred Buffalo Bill Cody called “Scouts of the Prairie.”
Unlike Hemingway, Buntline was not a drinker and gave speeches supporting temperance; still, the two writers seem to have been cut from the same cloth. It seems criminal to travel across the country to a Hemingway seminar, deliver the closing keynote presentation and not bring up the Buntline story.
Of course, it is not just the connection the two writers seemingly share but Buntline’s connection to piracy that makes him the perfect addition to the story. As I’ll be talking about pirates and piracy in the Florida Keys, one story I’ll be sharing is that of the island chain’s legendary pirate, Black Caesar.
In 1847, Buntline wrote two pirate novels. The first was “The Black Avenger of the Spanish Main: Or, the Fiend of Blood.” The story had a Black Caesaresque theme and was about a servant who eloped with his master’s daughter and turned to a life of piracy. The second was “The Red Revenger: Or, the Pirate King of the Floridas.” In Buntline’s opening, he writes, “Off the island of Matecumba, distant perchance a mile from the reef, lay a vessel becalmed, which in her appearance was so strange that we must describe her.”
Buntline also wrote the short story, “Jack Weatherwax: The Wrecker of Caesar’s Creek, A Tale Of The Florida Reef in the Olden Times.” Though the story tells the tragic tale of the wrecker Weatherwax, Buntline tells his version of the story of how the creek received its infamous name Black Caesar’s Creek, “because it was formerly the hiding place and rendezvous of a noted pirate known as Black Caesar, who was destroyed, and his gang broken up, by Commodore Porter’s expedition, in 1822 or 3 — perhaps by the same gallant ‘Old Plug,’ of whom I spoke in the Mercury not long since. It is a dark and crooked lane of water, leading to the inner bay, shaded by shelter on either side by high mangroves, and afforded an excellent hiding place for the pirates, who could suddenly dart out upon the merchant vessels passing up or down the Gulf Stream.”
