IF in any way early Key West deserved a reputation for lawlessness, it had good reason. Located at the farthest end of a vast wilderness, the island knew no permanent residents until 1822, and was initially and problematically governed by a military force. When William A. Whitehead settled there in 1831, he came from a place that had known civilian government for more than a century and a half. On Key West the rule of law and the orderly conduct of public business were comparative novelties.
Civilian affairs in Florida during its territorial period were the responsibility of a distant national authority, and were managed by men who owed their positions more to political connections than to on-the-ground experience. Florida’s early legislators, judicial officers and governors were all appointed by the executive in Washington. The territorial capital of Tallahassee, from Key West’s point of view, seemed equally remote.
In a significant step toward representative government, the territory’s unicameral assembly, the Legislative Council, became an elective body in 1826, with a single delegate sent from Monroe County, including the county seat of Key West. By an 1828 act of this body, Key West obtained a form of home rule, southern Florida’s first town council.1
The Keys proved a natural seedbed for politics, and early campaigns were rife with improprieties. The captain of a revenue cutter was accused of twice landing his Charleston-based crew at polling places, in order to affect the results of local elections.2 In 1830, the required vote for Key West’s town council never took place; the following year, three of the seven winners allegedly didn’t know they were candidates. The Legislative Council was compelled to certify the disputed results of this election, the seats of the unwitting, presumably unwilling victors going to three others–one of them William A. Whitehead. And it was mandated that all future Key West elections be advertised.3
Thus Whitehead, within weeks of assuming the duties of collector of customs, found himself also a council member, in the year the town first tried to raise funds by a tax on real estate. While agreeing with the idea in principle, he was obliged to point out that the town’s present charter authorized no such levy.4 Some of the already collected taxes would have to be refunded, and Whitehead wryly recommended that future councilors “have the good of society sufficiently at heart, to induce them to read the Act incorporating Key West;–in order that it may not be left to particular circumstances to ‘discover’ what that document contains.”5
At the beginning of 1832, the territorial legislature expanded the town’s taxing powers with a new charter, and made of the town of Key West a city. A mayor and six aldermen were now empowered to raise revenue on real property, including “unimproved lots” taxable up to 12½ cents per acre.6
This newly emboldened local government was destined, however, to lock horns with Richard Fitzpatrick, recently reelected as county representative to the Legislative Council. Fitzpatrick’s feuds with Key West’s city fathers predated the city itself, and as a justice of the peace, he remained a powerful figure even after losing his Legislative Council seat in 1833. Returning to the legislature at the beginning of 1835, he would prove still more disruptive to affairs in the city.
On the strength of a petition from “Sundry Inhabitants” of Key West for the abrogation of its charter,7 Fitzpatrick brought forth a bill to that end. The act of repeal, passed on 24 January and made law on the 29th, prohibited all but county and territorial taxes within the city limits; it required that all money collected “in any manner whatsoever” and all related records be turned over to justices of the peace; and it levied on former city officials a $50 fine for each refusal.8
Although there was little doubt that Fitzpatrick himself had been the leading force for repeal, if not its instigator, Whitehead’s policy as editor of the Key West Enquirer was to abstain from “party controversy.”9 He took refuge, initially, in satire. Donning the persona of “Timothy Pull-Down,” an imaginary merchant bent on mayhem, he published a plan to sell instruments to itinerant musicians “desirous of disturbing the peace of the community”; hogs and goats to wander the city at large; and numerous other nuisances, “calculated to make Key West as ‘horrible’ a place as its enemies could wish.”10
Wielding a more serious pen on the subject of the upcoming Legislative Council elections, Whitehead pleaded, without naming names, for a delegate who would restore the charter, and guarantee “the privileges that the inhabitants of every town or city in the Union are allowed to enjoy….”11 Not all of Key West agreed, of course; even among Whitehead’s associates in the custom house, there was division. Hence he allotted space in the Enquirer to the jests and fulminations of Adam Gordon, his deputy and the late mayor, but also to the critiques of his inspector and sometime protégé Stephen R. Mallory, a Fitzpatrick ally, although Whitehead could not keep from casting aspersions on Mallory’s style, or on his arguments.12
Whitehead could no longer pretend patience with the government in Tallahassee: the charter’s revocation was of a piece with a tendency in Florida “to repeal or modify, each session, about nine out of every ten acts which previous Legislatures have enacted.”13 “Laying aside all satire,” he stated his conviction that most Key West citizens desired an effective local government, and that “no commercial place of equal extent” needed one more.14 Even in the pro-charter party’s defeat he found vindication: Fitzpatrick, with a slim three-vote victory at the Key West polls, would have come in a distant second if not for the many out-of-towners who had cast ballots there.15
With little likelihood of remedy in the territorial capital, Key West’s mayor and council, together with Whitehead and two dozen other leading citizens, petitioned the United States Congress to restore their right of self-government.16 There was slim chance of the charter repeal being upheld in Washington, and while no Act of Congress materialized the petition seems to have had its effect in Tallahassee: Key West was soon rechartered, albeit with a somewhat diminished power to tax.17
Richard Fitzpatrick’s sway over the island’s affairs had also weakened, although he remained preeminent on the territorial level, becoming president of the legislature at the start of 1836. His struggle for control in South Florida was soon to take a new and devilish turn. But in Whitehead’s pragmatic view the city of Key West, having won back its local government, had best “adopt the principle of the homely adage, and endure what we cannot cure; we shall therefore go to the polls with a determination, so far as our own vote will effect it, to make the best of the privileges so kindly restored to us by the Legislative Council.”18
Elections, duly held, brought Key West a new mayor and council, and with them new hope. As editor of its only newspaper, professing to have spoken and acted always on behalf of “the good of society, and the prosperity of the place,”19 Whitehead had exerted an influence as far-reaching as any citizen’s.
But if gratitude was due for the restoration of Key West’s legal authority, Whitehead felt it his to give, not to get. So, at least, were his thoughts on departing the island with his family to spend the coming summer in the north: “Truly thankful are we,” he reflected, “that it can no longer be said ‘There is no government here.’”20
Copyright © 2022 Gregory J. Guderian
 The first charter, passed and signed into law in January 1828, was entitled “An Act to incorporate the island of Key West.” Its text, however, incorporated seven named individuals as “the Town Council of the town of Key West.” This was supplanted in November by “An Act to incorporate the Town of Key West,” defined as “all the free white inhabitants of that part of the Island of Key West in the county of Monroe, comprehended within the limits prescribed by the plan of said town, now on file in the clerk’s office of said county.” This plan is thought to be the unlocated map of H. L. Barnum, on whom see my earlier post The forerunner. It was replaced by William A. Whitehead’s “Map of the Town of Key West together with the island” executed the following year. See Acts of the Legislative Council of the Territory of Florida, passed at their 6th session, 1827-8 (Tallahassee 1828) 61-64; Acts of the Legislative Council of the Territory of Florida, passed at their seventh session 1828 (Tallahassee 1829) 296-298.
 Theodore Owens, Key West, 8 August 1829, to President Andrew Jackson, 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) 256-258; see also Key West (Fla.) register, and commercial advertiser 4 June 1829 2:4.
 “An Act concerning the town of Key West,” in Acts of the Legislative Council of the Territory of Florida, passed at their ninth session commencing January third, and ending February thirteenth, 1831. With also, the resolutions of a public or general character, adopted by the Legislative Council at said session (Tallahassee 1831) 15. Attorney William Hackley recorded the names of the seven councilors first elected, including R. G. Porter, George E. Weaver and Robert B. Stanard, none of whom had sought the office. Benjamin B. Strobel in the inaugural issue of his Key West Gazette named himself, William A. Whitehead and Fielding A. Browne as councilors, along with four of the men named in Hackley’s diary: President David C. Pinkham, Pardon C. Greene, Joseph Cottrell and George E. Weaver. One of those named by Hackley, David L. Wakely, was not included in the roster of the Gazette. William R. Hackley, Diary, in Goulding Collection, Special Collections, Florida State University Libraries, Tallahassee, MSS 0-128, entry of 3 January 1831; Key West (Fla.) gazette 21/28 March 1831 2:3.
 “Proceedings in Town Council,” Key West gazette 26 October 1831 3:1.
 G. P., “Communicated,” Key West gazette 21 December 1831 2:3; cf. Key West gazette 28 December 1831 2:2.
 “An Act to incorporate the City of Key West,” Acts of the Legislative Council of the Territory of Florida, passed at the 10th session, commencing January 2d, and ending February 12th, 1832 (Tallahassee 1832) 11-13; Key West gazette 29 February 1832 1:2-3. The exclusion from the city’s jurisdiction of lands in the northeast part of town, currently “used and occupied by the United States for the erection of barracks and for other purposes,” had been Whitehead’s recommendation, probably anticipating their sale by the proprietors to the national government: Key West gazette 28 December 1831 2:2.
 Minutes of 8 January 1835, Journal of the Florida Territorial Legislative Council, January 5 – February 10, 1835, State Archives of Florida.
 “An Act, to repeal An Act, entitled An Act to incorporate the City of Key West,” Acts of the Governor and Legislative Council of the Territory of Florida: passed at the thirteenth session, begun and held at the city of Tallahassee, on Monday Jan. 5th, and ended Saturday Feb. 14th, 1835 (Tallahassee 1835) 301-302.
 “Approaching election,” The enquirer (Key West, Fla.) 3 October 1835 3:2. Reporting on a piece in the Florida Herald that treated the repeal of the charter “in the terms it merits,” Whitehead noted without comment its charge that the abrogation was due “entirely to the member from Monroe County,” “Rights of Key West,” The enquirer 1 August 1835 3:1. Months later, when Stephen R. Mallory objected that Whitehead had thus “deviated from the path of strict neutrality,” he responded: “This we unequivocally pronounce untrue, and refer to the paper for proof of what we state, for if our readers will trouble themselves so far as to look at the Enquirer of that day, they will find, we were adverting to an article that we had seen in a St. Augustine paper, the writer of which had made the observation alluded to. So strong was our desire to avoid any cause for the imputations now cast upon us, that we did not copy the article in extenso, as it was far more personal than any thing relating to the abolition of the charter that had appeared in our columns.” The enquirer 31 October 1835 2:4-3:2. The 17 June 1835 issue of the Florida Herald to which Whitehead referred is not thought to survive. He would restate his intention to keep the Enquirer “as free from controversy as possible,” without however sacrificing the right of “candidly stating his own sentiments….” The enquirer 5 December 1835 3:1.
 The enquirer 21 February 1835 3:2-3.
 “Approaching election.”
 Whitehead printed three letters (two in answer to “Timothy Pull-Down’s” satirical advertisement) and two editorial pieces attributable to Gordon in The enquirer 21 March 1835 3:2, 11 April 1835 3:1, 3:2-3, and 6 June 1835 3:1-2. Two letters of Mallory’s (signed “E. B. M.” and “M. E. B.”) with withering criticism by Whitehead appeared in The enquirer 24 October 1835 3:2 and 31 October 1835 2:4-3:1. Gordon was to succeed Whitehead as collector of customs in 1838, and Mallory would take Gordon’s place in 1845.
 “The late corporation,” The enquirer 11 April 1835 3:1-2.
 The enquirer 28 March 1835 2:1-2; “Approaching election.”
 “The prospect,” The enquirer 17 October 1835 3:1.
 “Memorial to Congress by inhabitants of Key West,” 16 November 1835, in Clarence Edwin Carter, ed. The territorial papers of the United States. Volume XXV. The territory of Florida 1835-1839 (Washington 1960) 196-197.
 “Key West charter,” Key West (Fla.) inquirer 13 February 1836 2:2; “An Act to incorporate the City of Key West,” Acts of the Governor and Legislative Council, of the Territory of Florida: passed at the fourteenth session, begun and held at the city of Tallahassee, on Monday January 4th, and ended Sunday February 14th, 1836 (Tallahassee 1836) 59-62.
 “Reorganization of the city government,” Key West inquirer 2 April 1836 3:3-4.
 “Something like censorship of the Press,” Key West inquirer 12 March 1836 2:1.
 Key West inquirer 16 April 1836 3:2. Whitehead’s remark concludes the report of a conversation between a passenger and the pilot of a vessel entering Key West harbor. In the University of Florida copy, someone wrote across the article in large script the single word “Fact.” The same paper records Whitehead sailing “to-day for Charleston” with “Lady, child and servant.” Key West inquirer 16 April 1836 3:4.