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Sunday Favorites: The Oldest Pirate


Juan Gomez lived to be 122. At least, that’s the number he gave people when they asked about his age. The retired pirate met his end in 1900, when some local fisherman found him floating alongside his tiny boat. From the looks of it, Gomez had become entwined in his cast net while fishing and drowned.

Photo of Juan Gomez on Panther Key

It was a fitting end to a former pirate that had served as Jose Gaspar’s protégé. Gomez was a man who had pillaged and spent a gold fortune most folks never see their entire lifetimes. 

Born on the Portuguese Island of Madeira in 1778, Gomez never had much of a taste for the mainland. He ran away at age 15 after his parents moved him to a new home in Lisbon, Portugal. After finding himself in France, Gomez enlisted as a cabin boy on a French naval warship. 

However, he deserted his post in the West Indies, opting to crew on a Spanish merchant ship, Villa Rica.  

Villa Rica was one of the last Spanish Galleons, or multi-decked sailing ships used by Europeans from the 16th through 18th centuries. Gomez visited some of the most exotic places in the world aboard the ship, including Cadiz, Barcelona, Puerto Rico and many other destinations in South America.

Gomez’s stint aboard the Villa Rica was cut short in 1801, after the vessel was blown off course during a hurricane. Pirates led by Jose Gaspar captured and looted the ship, finally setting it afire and killing the entire crew, except for Gomez.

As was Gaspar’s custom, he knifed the seamen in the back then sent them into a watery grave. Gaspar must have seen something in Gomez that persuaded him to spare his life. Gaspar took Gomez and 11 young Mexican girl passengers, all bound for a school in Spain, with him. 

Gomez watched as the ablaze ship he called home sank into the watery depths approximately 40 miles off the Florida coast. 

Gaspar gave 10 of the 11 girls to the members of his crew. He kept the last one, Josefa, who was rumored to be the daughter of the Spanish Viceroy of Mexico, for himself.

Gomez soon became a full-fledged member of Gaspar’s crew. When trust was established between the two men, Gaspar shipped Gomez to Europe to carry out the murder of his greatest enemy, Manuel de Godoy, the Spanish Prime Minister. 

The Villa Rica was one of the last Spanish Galleons. 

Before Gomez’s mission could be accomplished, he was drafted into a border patrol unit near the French border where he allegedly met Napoleon Bonaparte who told him he’d make a good soldier some day. 

Gomez deserted his post as soon as he could get away, eventually joining the crew of a slave ship, which sailed between parts of Africa and the West Indies. 

In 1818, Gomez once again captured by Gaspar’s ship and once again his life was spared. 

Over the next few years, Gomez lived with Gaspar on Boca Grande, which Gaspar had converted into his own island of debauchery and served as a home base for he and his crew. 

Gaspar finally met his end when an American warship in Charlotte Harbor attacked him. Gomez watched the assault from shore and narrowly escaped death by taking a small sailboat down Pine Island Sound to Panther Key, one of the 10,000 islands that border the western point of Florida south of Naples.

Gomez, now about 43 was not ready to retire from piracy just yet. After laying low for a while on Panther Key, Gomez joined the crew of another slave ship where he stayed for the next five years. 

The pirate couldn’t seem to stay away from political strife. In 1831, he became involved in the Cuban revolt against Spain. Again he narrowly escaped death by fleeing in a small rowboat. When he was finally rescued by a passing ship, he was near death, starving and sunburnt,. 

Piracy had come to an end in Florida. So Gomez retired from the industry and survived by succumbing to a simple mundane lifestyle, fishing and doing odd jobs to make ends meet. 

Perhaps that’s why Gomez joined General Zachary Taylor’s command and served as a scout during the second Seminole War. Gomez was involved in the Battle of Okeechobee on Christmas Day in 1837 when 26 U.S. troops were killed and 112 injured.

For his next career move, he herded native piney wood cattle along the Gulf Coast. The cattle were sold and shipped to Cuba. 

Finally at age 77, Gomez returned to Panther Key where he lived out the what seemed to be the last of his days in a Palmetto shack.

It wasn’t until 1870 that the first white man in the area, Walter Collier, first discovered Gomez still living on the island. Collier reported that Gomez was “well supplied with money.” He also told his friends that the old man, then 92, could still climb and coconut palm to retrieve coconuts. 

Gaspar or Gasparilla took a liking to Gomez and spared his life on two occasions. 

Collier, who shipped supplies to settlements from Cedar Key to Key West, maintained a relationship with Gomez from 1870 until his death in 1900. He would later convey that Gomez would often disappear for days in his little sailing skiff. The excursions were always kept secret and Collier assumed he was out digging up buried treasure. 

However when asked about his mysterious trips, Gomez told Collier he was out “hunting a wife.”

In 1884, to Collier’s surprise, Gomez returned from one of his expeditions with a woman. The couple told Collier they had been married in Tampa. Collier reportedly said the woman was “well preserved” for her 78 years. 

As the years past, Collier, who owned a trading post on Marco Island, began to notice that Gomez was going long periods without buying supplies. At one point, he speculated that three months had gone by since the old man had been to his trading post. 

When Collier visited the island to see what was going on, he found Gomez and the women looking very thin. They said they had been surviving on coconuts, palm cabbage, oysters and clams. Apparently Gomez had outlived his treasure stash and did not have a dollar to his name. 

Collier commissioned officials of the newly formed Lee County to help the elderly couple. The commission said they would allow Collier to deliver $8 of food and clothing per month to the starving couple, to be billed directly to the county clerk.

Eventually an admirer of Panther Key, Sampson Brown, told Gomez he would build him a sturdy home if Gomez would relinquish his squatter’s rights to the key. Brown planned to outlive the 112-year-old man and claim the island for himself, but he dropped dead about a year later leaving the ex-pirate with a nice shack and an island to himself once again. 

Word traveled that Gomez was living on the small island, and he would often get visitors who were awed by his tales of piracy on the seven seas. Sometimes, Gomez would even draw them treasure maps promising them riches from Gaspar’s lost fortune, for a small fee. 

Gomez lived to the ripe old age of 122. It was on a hot summer day that he became entangled in his own cast net. It wasn’t until a few days later that he was discovered by some local fisherman and buried in an unmarked grave on his island Panther Key. While the old man finally met his end, his story will live on in history. 


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