When East Florida and West Florida were still Spanish territories, they were wild, sparsely-populated frontiers. 

The Spanish had established two ports. On the Atlantic coast, there was the Spanish port of St. Augustine. Along the long curve of land that spills into the Gulf of Mexico, there was the port at Pensacola. Hoping to begin to tame the land, Spain encouraged settlement of the territory and offered land grants to those willing to brave the frontier and make at least some small portion of it inhabitable.

The acquisition and development of the property were sanctioned through a program of land grants implemented in 1790 and would come to affect Key West’s colorful history. These property transactions are referred to as Spanish Land Grants. There was good news for the Spanish landowners when the territory was transferred to the American government under the Adams-Onis Treaty. If adequate documentation could be shown to American authorities, the land grants would be recognized. 

In the Florida Keys, only a handful of islands had been legally acquired while they had been under Spanish rule. The Baccas Keys land grant was originally assigned to Francisco Ferreira. The transaction occurred after Ferreira, who had been in St. Augustine at an opportune time, petitioned the Governor on Jan. 4, 1814, “to grant him in absolute property a Key situated among those called the Florida Keys, and is also known as Key Baca and also four small islands which are situated in the vicinity. ..”

The petition was approved the next day, “as the services rendered by the petitioner are well known, and in consideration of the great losses which he has suffered by the Revolution.” The 1814 Ferreira land grant included the islands recognized today as Key Vaca, Long Key, Knights Key, Boot Key and Duck Key. 

Key West was the other primary Florida key legally acquired during Spanish ownership. Before it became an American property, the island’s second to the last owner was Don Juan de Estrata. In 1815, Estrata sold the island to Juan Pablo Salas, the island’s last legal owner under Spanish rule, and Salas sold the island to its first American owner, John Simonton.

John Watson Simonton was born in New Jersey in 1791. Simonton grew up a merchant and businessman operating between Mobile, Alabama, and Cuba. Because of the route he traveled, he understood Key West’s advantageous position. He also understood the importance of the island’s naturally deep harbor and easy access to the shipping channels between the Mississippi River, Gulf of Mexico and the Atlantic coast. On Dec. 20, 1821, Simonton paid Juan Pablo Salas $2,000 for the island, a sum he paid in full.

One month later, on Jan. 19, 1822, Salas sold the island again, this time to an attorney named John Strong. Adding some Key West flavor to the island’s already colorful hues, Strong, the attorney, turned around and sold the island twice, too. He sold Key West to both John Geddes of Charleston and George Murray, president of the Legislative Council of the Territory of Florida.

Though the Florida Reef and the Florida Keys had been included in the Adams-Onis Treaty, Lt. Mathew Perry of the U.S. Navy was given orders in February to sail the U.S. schooner Shark to Key West, survey the island and harbor, and officially declare the island a U.S. possession. By the time Perry arrived at Key West and raised the first U.S. flag over the island on March 25, 1822, several families were already calling the island home, and they gathered to witness the event.

This year, the bicentennial honors Perry’s raising of that first flag over the island in 1822. In the meantime, thinking he was the undisputed owner of Key West, Simonton took on three partners, selling parcels of the island to John Whitehead, John Fleming, and Pardon Greene. All of these men remain prominent names of Key West streets: Simonton, Whitehead, Fleming and Greene. It took years for the courts to wade through the documents and determine the island’s rightful owner. Simonton was declared the legal owner on May 23, 1828.

In other bits of period history, Monroe County became the Florida Territory’s sixth county when it was established on July 2, 1823. Named after the then sitting and fifth president of the United States, James Monroe, county boundaries originally extended north to the southern shore of Lake Okeechobee and west to the Gulf of Mexico. Key West, the most populated community in the territory, was named the county seat. On Jan. 8, 1828, the city of Key West was officially incorporated. 

That same year, Key West was added to the list of St. Augustine and Pensacola as an official U.S. port of entry.

If you would like to have the Weekly delivered to your mailbox or inbox along with our daily news blast, please subscribe here.

Brad Bertelli is an author, speaker, and Florida Keys historian. His latest book, “The Florida Keys Skunk Ape Files,” is a fun blend of two of his favorite subjects — Florida Keys history and the Skunk Ape.