LIEUTENANT Matthew C. Perry guided the Shark, battered by a spell of “boisterous weather,” into Havana harbor for repairs. The damage to the schooner, though slight, signified that its next assignment, to police the Caribbean and Gulf of Mexico, was to be no easy affair.
Of late the Shark and its steely skipper had helped deter slave traders and laid the foundations for a freedmen’s colony that would evolve into the Republic of Liberia. Further adventures and dangers awaited them on distant horizons from Africa to Mexico, the Mideast to the Pacific, but in Spring 1822 the Shark had one comparatively peaceful mission. With Florida newly ceded to the United States by Spain, the Secretary of the Navy dispatched Perry to claim an archipelago reaching from Cape Florida some 180 miles into the Gulf, known as the Florida Keys.
The ceremonies took place on the southernmost island, which Perry however was not the first of his countrymen to claim. John W. Simonton, a merchant from New Jersey with business interests in Cuba and the Gulf, had bought the island the year before from Juan Pablo Salas and his wife for “a valuable consideration,” enumerated elsewhere as the neat sum of two thousand dollars.1
As Perry took possession, he and the U.S. government were clearly yielding to the desires of Simonton and his associates. Petitioning Congress for the island to be made a port of entry for foreign goods, Simonton had extolled its many virtues: its sheltered, deepwater harbor, abundant supply of wood, fresh-water springs and copious salt deposits, but above all its strategic value both commercial and military for the United States. All of these advantages Perry included in his report to Navy Secretary Smith Thompson.2 Perry further obliged the proprietors (and himself, he said) by giving the island Thompson’s name, but its Spanish name persisted in a distorted form: on English-speaking tongues, Cayo Hueso became Key West.3
In anticipation of the U.S. takeover, Key West had seen a spurt of building and land clearing. Later Simonton would assert that he established himself there “when no living person was on said island,”4 but numerous “improvements” already underway were making the place into “a considerable Settlement.” Simonton had also begun to sell shares of Key West, with the result that on 25 March Perry could name three other proprietors in attendance “on the Occasion of planting the Standard.” They were John Warner, the American agent in Havana, and two merchants from northern states having commercial interests in the South: John W. C. Fleeming of New Bedford, Massachusetts, and John Whitehead of Perth Amboy, New Jersey.5
The half-brother of William Adee Whitehead, John had first seen the Keys by accident after being shipwrecked in the Bahamas. In his dealings on Key West he acted alternately on his own behalf and that of his father, who never set foot there but found himself the owner of one-fourth of the island in 1826.6 His purchase was one of a welter of divisions and transfers taking place under a cloud of disputed title which cast a shadow on the sale by Salas.7 With Simonton’s claims finally confirmed, in part by Act of Congress, John Whitehead had one more obstacle to overcome: a father’s refusal to let his youngest son join his oldest on Key West.
That resistance would falter and fail, and in his nineteenth year William A. Whitehead went to sea–“a most important and novel event.”8
Copyright © 2017-2021 Gregory J. Guderian
 “John W. Simonton vs. The United States. For Cayo Hueso, or Key West,” 25 November 1823, in Asbury Dickins and James C. Allen, edd. American state papers. Documents of the Congress of the United States, in relation to the public lands… (Washington 1859) 4:705-707.
 “Memorandum by John W. Simonton,” 7 December 1821, in Clarence Edwin Carter, ed. The territorial papers of the United States. Volume XXII. The Territory of Florida 1821-1824 (Washington 1956), 411-412. “Memorial to Congress by John W. Simonton and Associates,” 31 January 1822, ibid. 352-353. “Matthew C. Perry to the Secretary of the Navy,” 28 March 1822, ibid. 385-388.
 William A. Whitehead preserved a local tradition–worthy of “all the credit conferred upon the same authority in other parts of the country”–tracing the name to the gruesome aftermath of a last-ditch battle between two rival Indian tribes: “This battle strewed the Island with bones, as it is probable the conquerors tarried not to commit the bodies of the dead to the ground, and hence the name of the Island Cayo Hueso (in Spanish “Bone Key”) which the English, with the same ease that they transformed the wine Xeres Seco into ‘Sherry Sack,’ corrupted into ‘Key West.'” Notices of Key West for John Rodman Esq. St. Augustine, written December 1835, 1b, manuscript copy in Florida Miscellaneous Manuscripts Collection, P. K. Yonge Library of Florida History, Special Collections, George A. Smathers Libraries, University of Florida. The text was printed in Rember W. Patrick, ed. “William Adee Whitehead’s Description of Key West,” Tequesta: The journal of the Historical Association of Southern Florida 1:12 (1952) (61-72) 62-63.
 The wording given comes from a copy of the memorial of 25 November 1823 digitized by the Florida State Archives; the printed version reads “where no living person was on said island.” “John W. Simonton vs. The United States,” 706.
 According to William A. Whitehead, Simonton sold a half-interest in the island to Fleeming and John Whitehead and a quarter to Warner and Warner’s deputy John Mountain, “soon after making the purchase” on 20 December 1821. Notices of Key West 2a (Patrick 63).
 Historical Records Survey, Spanish land grants in Florida (Tallahassee 1940-41) 5:87 no. 13.
 See Mary Haffenreffer and Karl Haffenreffer, “Deeds and misdeeds: The title to Key West 1815-1833.” Florida Keys sea heritage journal 21:4 (Summer 2011) 6-12.
 “Childhood and Youth of W. A. Whitehead 1810-1830.” A transcription of this memoir is held by the Florida History Department, Monroe County Public Library, Key West, Florida, and by the P. K. Yonge Library of Florida History, George A. Smathers Library, University of Florida; page 23 of the transcription contains the reference.