“I considered them,” Commodore David Porter declared with satisfaction, “as merely tolerated on the island….” So slight was the Navy commander’s regard for claims of the self-styled proprietors of Key West.1
Yet his presence, arguably, was the result of these men’s enterprise, especially that of the island’s original purchaser, John W. Simonton, who first caused the U.S. government to take notice of this southernmost point in its most recently acquired territory as “a harbour and rendezvous for our vessels of war, it being one of the most commanding places on the whole coast of Florida.”2
At least on this assessment, even through years of discord over their respective rights, the commodore and the proprietors would agree.3
Porter’s stated mission, however, to eradicate piracy from the Caribbean, had broader implications. As commerce in the Gulf of Mexico expanded, worries about European interference in the region loomed large. Key West, poised at the entrance to the Gulf, seemed the spot from which the nation’s entire southern flank could be defended, and the future of a new American empire secured.4 To the Gulf, in Porter’s mind, Key West would be “what Gibraltar is to the Mediterranean, and the one thousandth part of the money that has been expended on the one, would make the other all that could be desired.”5
But to the worldly fortunes of the proprietors, who included, besides Simonton, New England merchants John W. C. Fleeming and Pardon C. Greene and, representing their father in New Jersey, John Whitehead and later his brother William, Porter’s arrival spelled devastation. The “one good building” Fleeming and John Whitehead had managed to complete was soon hemmed in by navy storehouses, workshops, officers’ quarters, barracks and other structures, all meant for military use and erected in utter disregard of the proprietors’ plans and protests. Islanders’ livestock was destroyed. Wood they had cut and stacked was expropriated without payment. Any unauthorized construction for private purposes could lead to arrest.6
For three rancorous years, the proprietors were thwarted in their designs, although it’s certain that they bore some of the blame. After 1826, following three years’ occupation and the loss of many sailors and marines to yellow fever or other maladies, the Navy largely withdrew to Pensacola, and some of those left behind began to see the proprietors as dictators in their own right, ruling the island in much the same arbitrary fashion. Key West appeared to have exchanged one brand of tyranny for another.7
At the same time, there seemed to be little in the way of recognized authority, civil or military. By 1828 there were appeals from many quarters for the return of a military presence, both to protect shipping from a resurgence of piracy and to regulate the behavior of the inhabitants. Key Westers were a highly heterogeneous population: a newly appointed judge saw many of them as having “very erroneous & imperfect ideas of liberty,” tending “as soon as they land on our shores … to do as they please….”8
It was likely no accident that young William A. Whitehead made his maiden voyage to Key West at this time and in these circumstances. Even before all doubts as to their ownership were removed, the proprietors commissioned the 18-year-old Whitehead to survey the island and its natural resources, and map out the parcels allotted to each. We may never know whether this survey was meant to guard their lands from arbitrary seizure, prepare them for sale to the government, or simply provide for a less unfriendly situation than had existed under David Porter. But all looked to the imminent return of U.S. forces, and all were mindful of its implications.9
In March 1829, the Key West Register reported that the Army had agreed with the proprietors on a site for a garrison, and contracted with the collector for a waterfront battery on the grounds of the custom house.10 A lookout tower was planned as well.11 Forecasts of the size of the military presence varied from one company to three, rumors flew of a permanent navy yard in the works,12 and the editor of the Register celebrated the “considerable augmentation of our population” that was bound to occur:
Besides a considerable improvement to our society, additional inducements will be held out for men of capital and enterprize to come amongst us, and will draw in their train others of inferior calculations, all conspiring to enhance the value of property, and give spirit and activity to every kind of business.13
Although the Register downplayed the scourge, optimism withered quickly when a yellow fever epidemic struck in August.14 The proprietors found it hard as well to shake off the vestiges of their prior subjugation: buildings remained from the period of Commodore Porter’s governance, and doubts lingered about how to dispose of them.15
In 1830, Congress appropriated money for building barracks and “ditching, draining, and clearing” the grounds,16 but a shipload of recruits reaching Key West the next February found no site reserved for them.17 While the men lived in tents on the north side of the island, their commander and his family were billeted at the custom house, as guests of the new collector William A. Whitehead, then less than a month into his tenure.18 Despite further funding from the national government, soldiers still lacked proper housing,19 and the military’s presence on Key West became a source of acrimony once more.
A mysterious letter, signed simply “X” and printed in a Washington paper (the Key West Gazette republished it in full, only to deem its charges “so false and perverted as to render it unworthy of notice”), accused certain “deeply interested persons” of having extracted public funds to “dig ditches and otherwise improve” private property, on an island of little value commercial or otherwise. Congress, the anonymous author claimed, had even been fooled by a “trumped up” tale about the risk of a pirate raid on the custom house, owing to the large sums of money kept there.20
Pardon Greene, the only one of the original proprietors resident on Key West, complained to the War Secretary of vandalism and violence perpetrated by enlisted men. Their commanding officer, responding with accusations of his own, pointed out that army discipline was all but impossible to enforce in a town “where almost every third house is kept as a grog shop by the most depraved of men…”21
Worse yet, when Lieutenant Timothy Paige took over the post in the last month of 1833, he renewed the charge that the government had been bamboozled. Finding no accommodations for his men Paige sent a blunt message to the War Department: “If Troops are to be stationed here it is necessary that Quarters be immediately built or they will all die.” A fortnight later, he argued at length for abandoning the station, weighing what he saw as the island’s insignificance, its inhospitable climate and its lawless citizenry against the exorbitant cost of keeping a garrison there. It seemed to Paige, from the shoddy buildings in place on which large sums had already been spent, that “the government never had its money more miserably and erroneously squandered.” He singled out Simonton and the “collector of the customs,” whom he didn’t name, as the authors of this deception.22
Paige enlarged his attacks on the Key West station the following year, reaching a national audience through the pages of The Military and Naval Magazine. But his predecessors at the post refuted them in the same journal a few months later,23 and there was little risk that the Army would pull up stakes, if only because Washington could not bear the embarrassment.
Paige had, however, made at least one worthwhile observation: if Key West mattered, it was as a seaport, not as an army base. “This place is important only as a marine station,” he wrote; “as such it should be occupied, if occupied at all, and fortified.” The Keys had had no naval station since David Porter left.
William Whitehead had started to make this case as early as 1832, on an extended visit to Washington during his second year as collector.24 In 1835, as editor of the Key West Enquirer, he printed extracts of Navy Department correspondence that, a dozen years earlier, had first drawn government attention to the island.25 He gave prominence to Commodore Porter’s judgments as well, written years after he had departed the place:
Key West has been tried, and is proved to possess all the advantages which are desirable in a naval depot and rendezvous. … Where, then, is the necessity of making further disbursements or useless experiments, when one has already been made in Key West, and has proved satisfactory?26
There’s poignancy in the decision to reprint Porter’s words, and the audacity of forgetting their author’s purported outrages. But Whitehead was prepared to marshal all his historical knowledge, his rhetorical skill and his influence as a newspaper editor to convince decision-makers of the “propriety of fortifying Key West.” Although the threat of piracy had passed, the prospect of losing control of the nation’s commerce should a foreign nation manage to capture Cuba, or even Key West itself, seemed to him a far greater one.27
The dangers imagined by Whitehead weren’t imminent, but others were: not from a powerful nation across the Atlantic, or unruly islanders, but from the Florida mainland in dugout canoes would calamity come to the Keys.
Copyright © 2021-2022 Gregory J. Guderian
 David Porter, Washington, 18 August 1824, to Lieut. James M. McIntosh, H. Rept. 189, 30th Congress, 1st Session (Washington 1848) (hereafter H. Rept. 189) (61-63) 62; cf. 42-43.
 Memorandum of John W. Simonton, Havana, 7 December 1821, H. Rept. 189 (12-13) 13.
 David Porter, Chester (Pa.), 29 December 1829, in S. Rept. 359, 24th Congress, 1st Session (Washington 1836) (hereafter S. Rept. 359) 13-15, reprinted (with alterations) in The enquirer (Key West, Fla.) 8 August 1835 3:2-4. Petitions of Simonton and his associates for compensation of their losses under military rule were brought before Congress on several occasions in the years following, the last time by Florida Senator Stephen Mallory in 1852. See S. Rept. Com. 48, 32d Congress, 1st Session (Washington 1852).
 The Navy’s senior officer predicted in 1823 “that the first important naval contest in which this country shall be engaged, will be in the neighborhood of this very Island.” John Rodgers, Washington, 24 November 1823, to Samuel L. Southard, in Documents accompanying the message of the President of the United States, to both houses, at the commencement of the First Session of the Eighteenth Congress (Washington 1823) 192-194 (193).
 “Porter’s Squadron,” Niles’ weekly register 19 July 1823 309. The comparison to Gibraltar would be expounded by Porter at greater length in 1829 (see S. Rept. 359 14-15), and sustained by the island’s press: “In the attainment of great national objects, we consider the situation of Key West as still more important. If strongly fortified, (and of which, it is fully susceptible,) it would be to the Gulf of Mexico, what the Rock of Gibraltar is to the Straits of the Mediterranean; and without such fortifications, in times of war, the whole of our western commerce will be at the mercy of every foe, possessing a strong naval force….” Key West (Fla.) gazette 27 April 1831 2:1.
 See esp. affidavit of Griffith W. Roberts, Remsen, N.Y., 3 November 1842, H. Rept. 189 (22-24) 22-23 and the many letters and affidavits printed ibid. 27-38, 54-61.
 Daniel Turner, U.S.S. Erie, 31 October 1827, to Charles G. Ridgely, in Clarence Edwin Carter, ed. The territorial papers of the United States. Volume XXIII. The territory of Florida 1824-1828 (Washington 1958) 930-931; Charles G. Ridgely, U.S.S. Natchez, Pensacola, 21 November 1827, to Joseph M. White, ibid. 975-977.
 James Webb, Key West, 27 October 1828, to Joseph M. White, in Clarence Edwin Carter, ed. The territorial papers of the United States. Volume XXIV. The territory of Florida 1828-1834 (Washington 1959) (hereafter Territorial papers XXIV) 112-113. Florida’s Legislative Council agreed on 19 November that it was “essentially necessary for the better protection of the revenue and of the inhabitants … that a Military force be established and located upon said Island.” Acts of the Legislative Council of the Territory of Florida, passed at their seventh session 1828 by authority (Tallahassee 1829) 300-301. Judge Webb’s letter was forwarded to the Secretary of War by Joseph White, the Territory’s delegate to Congress, who, it was claimed, had been working to bring back a military detachment since the summer: “Justitia,” “Communicated,” Key West (Fla.) register, and commercial advertiser (hereafter Key West register) 5 March 1829 2:2-3.
 Unsurprisingly, disagreements would arise as to whether land for the garrison would be sold to the government or ceded at no cost: see P. B. Porter, Washington, 24 December 1828, to Joseph M. White, Territorial papers XXIV 124; Joseph M. White, Washington, 30 December 1828, to P. B. Porter, Territorial papers XXIV 125; Gen. Alexander Macomb, Washington, 10 January 1829, to Col. George M. Brooke, Territorial papers XXIV 133-134.
 Key West register 12 March 1829 3:2.
 Commercial advertiser (New York, N.Y.) 7 May 1829 2:3; Evening post (New York, N.Y.) 2:4. Both items republish Delegate Joseph White’s circular letter from Key West register 16 April 1829.
 Key West register 16 July 1829 2:4, 23 July 1829 2:3.
 Key West register 30 July 1829 2:4.
 E. Ashby Hammond, “Notes on the medical history of Key West, 1822-1832,” Florida historical quarterly 46:2 (October 1967) (93-110) 104-105.
 See Lackland M. Stone, Key West, 21 April 1830, to Martin Van Buren, Territorial papers XXIV 401 and cf. ibid. 52n.; The papers of Andrew Jackson, Volume VIII, 1830 (Knoxville, Tenn. 2010) 766.
 Peter Force, The national calendar, for MDCCCXXXI. Vol. IX (Washington 18312) 230.
 James M. Glassell, Key West, 19 February 1831, to Col. Roger Jones, Territorial papers XXIV 503-504. Glassell’s company arrived with “materials for building barracks”: Key West gazette 21-28 March 1831 2:3.
 Transcription of an unpublished memoir under the title “Childhood and youth of W. A. Whitehead 1810-1830,” of which copies are held by the Florida History Department, Monroe County Public Library, Key West, Florida, and by the P. K. Yonge Library of Florida, George A. Smathers Libraries, University of Florida; page 32 of the transcription contains the reference.
 In 1835 Whitehead expressed “regret” at the unfinished state of barracks begun four years earlier: “A large and handsome building is left half finished, in a great measure exposed to the weather, and unless something is soon done towards its preservation or completion, the public purse will have been resorted to for no good purpose, as the building if left much longer, will require to be rebuilt to be of any utility.” “Fortifying Key West,” Key West (Fla.) inquirer 19 December 1835 3:1. See also “Indian affairs,” Key West inquirer 12 March 1836 2:2.
 The United States telegraph (Washington, D.C.) 7 June 1832 3:1; Key West gazette 18 July 1832 2:1-2. A correspondent in Washington alerted the editor of the Gazette to the attack in the Telegraph, and a handwritten note in the University of Florida copy of the Gazette identifies the informant as John W. Simonton: Key West gazette 18 July 1832 2:2.
 Pardon C. Greene, Key West, 15 October 1832, to Lewis Cass, Territorial papers XXIV 743-744; James M. Glassell, Key West, 14 December 1832, to Col. Roger Jones, Territorial papers XXIV 761-763. See also ibid. 795-797.
 Timothy Paige, Key West, 1 December 1833, to Roger Jones, Territorial papers XXIV 915; Timothy Paige, Key West, 15 December 1833, to Roger Jones, Territorial papers XXIV 926-928.
 T. P., “Key West,” The military and naval magazine of the United States 3:1 (March 1834) 19-20; J. M. Glassell and F. D. Newcomb, “Key West,” ibid. 3:4 (June 1834) 308. Paige’s reproaches were reprinted in The sailor’s magazine, and naval journal 6 (July 1834) 330-331 (but cf. 6:349), while Glassell and Newcomb’s answer was reprinted in the Key West (Fla.) enquirer 15 November 1834 3:2-3. Both letters were published in Charlton W. Tebeau, “Two opinions of Key West in 1834,” Tequesta: the journal of the Historical Association of Southern Florida 1:20 (1960) 45-49.
 In an unpublished journal held by the Key West Art and Historical Society, Whitehead noted a brief visit with Navy Secretary Levi Woodbury in which he “endeavoured to portray, as much as possible, the advantages of our little sea-girt Isle for a naval station.” Memorandums of peregrinations by land & water 2:. The conversation occurred in late April or at the beginning of May.
 The enquirer (Key West, Fla.) 21 March 1835 3:1, 3:3.
 S. Rept. 359 15; cf. The enquirer 8 August 1835 3:4.
 “Propriety of fortifying Key West,” The enquirer 14 November 1835 3:1-2; cf. “Fortifying Key West,” Key West inquirer 19 December 1835 3:1; “Fortifying Key West,” Key West inquirer 30 January 1836 2:3-3:1. Simonton forwarded the first of these items to Senator Samuel L. Southard, who was favorable to a permanent naval presence: J. W. Simonton, Washington, 13 January 1836, to Samuel Southard, Samuel Southard Papers, Princeton University, C0250, Box 56/2 (where the original clipping is preserved). Whitehead’s arguments were also taken up by newspapers in other Southern ports, whose remarks he duly reprinted: see “Propriety of fortifying Key West,” Key West inquirer 23 January 1836 2:1-2, “Fortifying Key West,” Key West inquirer 20 February 1836 3:1-2.