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The Maroons of Lostman’s Key & Capt. Jocelyn

By Craig Woodward

If you are a frequent reader of this column you know that the last issue mentioned how Lostman’s Key and River were named. That information piqued my interest into researching this story and finding out more of the details.

Lostman’s Key. Photo provided by Google map

It turns out that the villain in the story was a notorious character in Southwest Florida around the late 1800s. Captain Jocelyn (also sometimes spelled Joselyn) was described in 1875 as having “fame in Florida rivaling that of the most bloodthirsty pirate of the China Seas.” While he claimed to be an Englishman from Plymouth, the locals believed he was really an American from the northeast. Jocelyn had come to Florida during the Civil War as a union “blockade runner” and learned the coast well. After the war, he stayed in Florida sailing a green- hulled sloop named the “Flirt” (unusual at the time as most of the vessels were rigged as schooners,) and soon became “the terror of the whole coast as a pirate and murderer.” His notorious reputation included stories that at least four strangers and more than one Spanish fisherman had disappeared visiting him on an island on which he resided in Pine Island Sound (east of Captiva). All of those who disappeared, in his own account, had accidently “been knocked overboard by the boom of the Flirt’s mainsail and drowned.” Another description was that “he boarded unprotected and stranded or wrecked vessels on the Florida reef, robbed the passengers of money and jewelry, taken what he wanted of the cargoes and then decamped to some unknown rendezvous…” It was said that: “Because of his vile reputation, Jocelyn could only get seamen of very low character or strangers to sail with him.”

Fredrick Townshend, while on a trip in Florida, met Captain Jocelyn in Punta Rassa (now the mainland side of the Sanibel causeway) and described him as:

“…a more cut-throat-looking desperado I never beheld. Apparently between forty-five and fifty-five years of age, of medium height, very strongly built, with long black hair and beard, and flashing black eyes shaded by heavy eyebrows, he was quite the beau-ideal of a pirate, and his dress and arms fully kept up the character. He wore a blue flannel shirt and a ragged pair of pants tucked into long sea-boots, a red leather belt round his waist containing a revolver and long knife, and carried a rusty old rifle which he never let out of his hands.”

In 1862, John Weeks, who was then living at the entrance to the Barron River with his three daughters, relayed a story to William S. Allen, a former mayor of Key West, who later settled in the area now known as Everglades City and built his home where the Rod & Gun Club currently stands. Weeks’ encounter with Captain Jocelyn was described in his own words as:

“Thar’s one man though that’s treated me mean, an’ that I’d shore like t’ meet.  He kem yere a year or so ago an’ took all th’ stuff I hed, bananas, sugar cane an’ punkins, saying he’d be right back from Key West with a lot o’ grub for me, an’ I aint laid eyes on th’ damn scoundrel sence;  … His name is Joselyn – Captain Joselyn…” 

Allen told Weeks that he had seen Jocelyn in Key West and that he had a bad name. Furthermore, he knew that Jocelyn was under bond to appear in a U.S. court charged with smuggling, was once a pirate, was very rich, and had a hiding place among the Ten Thousand Islands where he hid the loot he stole from wrecked vessels.

So some time after Weeks relayed this story to William S. Allen, Captain Jocelyn met up with five soldiers in Key West who agreed to pay him $200 if he would take them in his sloop to Punta Rassa. They were dressed in civilian clothes, but Jocelyn understood them to be Army or Navy deserters. He hid them in his sloop while leaving Key West during the night and the following night anchored off Lostman’s Key, a remote area located approximately half way between Cape Sable and Everglades City.

Here it was reported that he ordered the “helpless credulous dupes to disembark, telling them they were on the mainland and that they would find a settlement with a saw mill where they could

get work a short distance back into the woods.” They were happy to leave “such a harsh and vile scoundrel” as Captain Jocelyn was and without a supply of food or water, and carrying only the clothing they wore, they landed on Lostman’s Key.

An unknown amount of days later, Scotty, the helmsman of Allen’s schooner “Jennie” along with George W. Allen (William S. Allen’s son) sailing north from Key West spotted a man on the beach waving a signal flag. Near shore they found five men, some “almost dead from hunger, thirst and exposure.” They had to be helped on board and, when on the deck, they were described as “wild of eyes, half crazed by anxiety, and emaciated by hunger and privation, they presented a woeful aspect.”

The youngest of the maroons and the most talkative, “Spud,” relayed the above story of what happened at the hands of Captain Jocelyn. To feed the men, the vessel stopped at Pelican Key where they collected several hundred clams, while George Allen shot two raccoons and two curlew (young white ibis). On their way to the Allen place in Everglades they stopped at Chokoloskee Island. George and Spud made their way into the center of the island where they found among the shell mounds an abandoned hut. Nearby, they reported that under a gumbo limbo tree, was a “cairn of alligator skulls, and turtle shells, all surmounted by several deer antlers. The place, in weird abandonment, bespoke only want, suffering, disaster or tragedy at some time in the dim past.”

At the Allen Place the maroons, to show their appreciation for being saved, worked hard and helped clear the land around the present day Rod & Gun Club. When they were healthy enough, they were taken north, except for Spud who stayed and worked for the Allens as well as working for a month with John Weeks before being  taken to Punta Rassa.

Because of this incident William S. Allen named the Key “Lostman’s” and the adjacent river also got the same name.  Meanwhile Scotty, the pilot of Allen’s schooner “Jennie,” said that he thought the name should really have been “Found Man’s Key.”

Craig Woodward moved to Marco Island in 1968 and has practiced law in Collier County since 1980. Craig is the Chairman of the Collier County Historical and Archeological Preservation Board.


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