Numbers to neighbors

Monroe County, Florida, in 1827.

NINE years after lowering the flag of Spain and fifteen years before statehood, Florida made its debut as a contributor to the United States decennial census. The national enumeration of 1830 separately counts whites, slaves and free persons of color, but records the names only of “heads of families.” Enslaved and free dependents remain anonymous, their relations unspecified. Kinship ties can only be guessed from age ranges and racial distinctions, leaving bounteous room for error.

The result for Florida is a blurred and fragmentary portrait, but one that still teaches something of its population when William A. Whitehead first came to the territory and just before he became a resident. Within the census schedule one also encounters, if fleetingly, citizens and denizens of the Florida Keys whose lives touched Whitehead’s own.

In January 1831 Whitehead settled at Key West, the seat of Monroe County and easily its most populous place. But the 1830 census made no distinction between his nearer neighbors and the distant residents of a county whose immensity then embraced not just the Keys but all of southern Florida, as far north as Charlotte Harbor on the Gulf of Mexico and present-day Fort Lauderdale on the Atlantic.

The recorded population of this vast territory was a minuscule 517. It comprised 451 free residents (a number that included 92 non-citizens, or “aliens,” and 83 “free colored persons”) alongside 66 unfree people parceled out among 17 slaveholding “families.” As was typical of a frontier area, the inhabitants were overwhelmingly male: white males outnumbered females three to one, compared with a ratio of 1.25 to 1 in Florida as a whole.1

Two-thirds of the county’s 112 white male “heads of families” had at least one dependent, perhaps a sign that some level of social stability had been attained. But where a dependent was adult, female and free, the nature of their relationship must be illuminated from other sources: wives, sisters, daughters and other female kin are all treated the same in the 1830 census.

The lighthouse on Sand Key, sketched by William A. Whitehead.

Whatever identity or autonomy was in women’s power to assert most often resulted from widowhood. This is known to be true in the case of the first name on the Monroe County census, Rebecca T. Flaherty. Widowed sometime in 1830, the 32-year-old Flaherty replaced her husband as keeper of the isolated Sand Key lighthouse nine miles south of Key West. She maintained this critical aid to navigation until her remarriage in 1834. The census counted three dependents, but only her sister is known to have lived with her full-time. A description and pencil sketch of Sand Key survive in one of Whitehead’s journals.2

A pioneer on Key West, Irish-born widow Ellen Russell Mallory was its best-known businesswoman in Whitehead’s day. According to her son Stephen she made “rather more than a living” running what Whitehead judged “the only respectable boarding house on the island.” The kitchen of Mallory’s hotel on Duval Street also fed many of the town’s bachelors, a fellowship that included Whitehead during his first three years as collector of customs.3 Ellen Mallory’s boarders may have been included with three enslaved persons in her eight-member household, making it among the larger ones in the county.

The widow Mallory’s status entitled her to join 138 other petitioners to Congress for a regular mail route in 1829. But that petition also listed at least two signatories named in the census as free people of color: Lucy Boston, the head of a family of four, and Felix C. Ruby, with a household of seven.4 It’s thought that Lucy Boston lived in the Keys undisturbed into the 1850s,5 but the increasingly harsh conditions for free Black or mixed-race residents may be better reflected in Ruby’s experience.

Following the lead of most southern states, Florida in the 1820s and 1830s banned the entry of free Blacks,6 outlawed interracial marriage or concubinage, stripped civil rights from people of color, and contrived to expel or enslave them. In 1832, Key West passed its own ordinance requiring that free Blacks and those of mixed race “be licensed or are liable to be sold.”7 A 9 pm curfew was imposed on all persons of color, slave or free, forbidding them to “play the fiddle, beat a drum or make any other kind of noise after bell-ring … without written permission from the Mayor or an Alderman.”8

Detail of Whitehead’s 1829 map showing the Ruby lot on Whitehead Street.

In 1829, when Whitehead drafted his map of the town, he had designated a handful of lots not in possession of the original proprietors. One of those bore the name of Ellen Mallory; another, on Whitehead Street, belonged to Ruby.

His status as a landholder and his claim to be a resident of the Bahamas may have insulated Ruby from the worst features of a hostile environment, but apparently not for long.9 In 1835, perhaps from the relative safety of Nassau, he engaged Whitehead to help settle his accounts,10 and a month later this notice featured in the Key West newspaper:


THE Lot of Ground on Whitehead St. belonging to Felix C. Ruby, with the buildings erected thereon, consisting of a Dwelling House, Kitchen, and Work Shop, all in tolerably good repair. The lot contains about half an acre of ground, and is surrounded by a good stone fence. The premises rent at present for about $10 per month.


While the degrees of independence enjoyed by Rebecca Flaherty, Ellen Mallory, Lucy Boston and Felix C. Ruby are hard to assess, these individuals were exceptions to be sure. In the world they inhabited, full freedom, wealth, prestige and influence were reserved for a segment of society expanding sometimes slowly, sometimes swiftly, but almost exclusively populated by white men. Both on the census and in the annals of politics, law, business, learning and religion, white males predominate. Some who came to southern Florida had little more than determination and ambition to propel them, others had wealth and well-established networks behind them. But even in the fluid and sometimes discordant society over which they believed it their right and duty to preside, power was not likely to be shared across lines of color or gender.

Robert B. Stanard was one of these men, a longtime Key West resident and the fourth person named on the 1830 census. Fortune briefly smiled on this attorney from Virginia in April 1831, conferring an appointment as auctioneer of shipwrecked goods for the county.12 When he succumbed to illness just one month later, Stanard was mourned as a pillar of the community. Although little more than 40 years of age at his death, he was pronounced “one of the oldest inhabitants of our town.” As there was no clergyman on the island Whitehead read the funeral service, at a gravesite that an obituary writer assured his eight survivors (among them three free persons of color, according to the census) “will not be neglected.”13

Not all of Key West’s white men were deemed worthy of such respect. Lemuel Otis, the gullible “old sea-captain” (the census places him in his fifties) who assisted young Whitehead with his 1829 survey, was gently mocked in print for what would prove a disastrous marriage to a much younger woman. Yet he still enjoyed the title of marshal or sheriff for the town, and kept its substandard jail.14

Replacing the jail was one of the tasks assigned to Whitehead soon after he became a Key West resident. He shared this commission with Lackland McIntosh Stone (the census gives his first name as Lacklan). A former member of the legislature from West Florida, Stone had arrived without his family to take up an appointment as U.S. marshal for the Southern District. (A scathing letter from Whitehead’s brother may have instigated the removal of Stone’s predecessor.15)

Lackland Stone would soon lock horns with the formidable Richard Fitzpatrick, scion of a South Carolina planter family whose entry in the 1830 census lists only him and 15 slaves. In 1831, while Fitzpatrick represented Monroe County in the territorial legislature, Stone united with Dr. Benjamin B. Strobel to launch the second newspaper in the island’s history. As fall elections neared, this became a vehicle for Stone’s campaign to unseat Fitzpatrick.16 Stone failed in the attempt, losing by a vote of 37-31,17 and departed the island well before completion of the jail. This left Whitehead to counter assertions by a Fitzpatrick-led grand jury that the jail was so poorly constructed as to be “entirely unfit.”18

A physician and amateur naturalist from Charleston, Benjamin Beard Strobel lived on Key West without dependents, according to the census of 1830. He supplemented his public practice of “Medicine, Surgery and Midwifery”19 with an appointment as surgeon to the army post in 1831, and election as town health officer and port physician in 1832.20 Stone and Strobel jointly published the Key West Gazette until October 1831, and remained chief editors until their departures from the island in February and September, respectively, of the following year.

David Coffin Pinkham of Kentucky was one of a vanguard of lawyers who migrated to Key West on creation of southern Florida’s first court in 1828. Although Pinkham was a generation older and had no knowledge of custom house matters, Whitehead’s first act as collector was to make him his deputy, and he didn’t regret the choice. He admired the older man’s “gentlemanly bearings,” and the two worked quite harmoniously together.21

But harmony didn’t prevail in all quarters. Having left Pinkham in charge for seven months while he attended to affairs in the north, Whitehead returned to complaints from a few citizens and merchants about unkind treatment received at the deputy’s hands. Resisting calls for Pinkham’s dismissal, Whitehead smoothed over matters where he could, but of the offended parties none was more relentlessly strident than Benjamin Strobel, a figure Whitehead considered too much engaged for anyone’s good in “matters of public or private disputation.”22

Before leaving the island, Strobel in a farewell editorial declared his “readiness to give redress to such as may be aggrieved,”23 and the editor’s continuing abuse impelled Pinkham to redeem that promise by challenging Strobel to a duel. Whitehead said of his deputy that, as he knew nothing of guns, to demand satisfaction in this way amounted to little more than “standing up to be shot at.” Nonetheless, Strobel and Pinkham met on the south beach in March 1833. On the first fire Pinkham lost his life, and Whitehead his deputy.24

The mass of Key West’s residents led humbler, quieter lives than these men, but even the island’s most sensational characters have imprinted themselves very unevenly on its past. Of those who didn’t die there as did Stanard and Pinkham, many like Richard Fitzpatrick and Lackland Stone moved on, unable to realize their ambitions. And without, for example, the services of a woman lighthouse keeper, or the talent and toil of an enslaved boarding-house cook, many of these men would have had very different lives, and deaths.

Whitehead was inevitably linked to others of his race and sex, and would shape Key West’s history from within the prevailing social frameworks rather than outside them. He accepted leadership positions in the town almost from the beginning, and as editor of the Key West Enquirer stepped into the void left by Benjamin Strobel. Yet, in these influential roles and in his relationships with other prominent men, a combination of youth and exceptional self-discipline set him apart.

He too was destined to leave Key West, but also to see the island in retrospect as home for the most important ten years of his life. Key West became for Whitehead a defining interval in two seemingly contradictory ways: the company of men superior in age, experience and education gave him a “fixed determination to render myself worthy” of their regard; the dangers, on the other hand, of “outside associations and influences” deepened his devotion to solitary reading and study.25

As it happens, Whitehead appears on no census return for Key West.26 If he did, there perhaps would be less, not more, of his story to tell.

Copyright © 2022-2023 Gregory J. Guderian

[1] The population schedules for Monroe County are designated “Territory of Florida, Southern District,” sheets 107-111. Fifth Decennial Census of the United States, 1830 (NARA Microfilm Publication M19), Record Group 29, Records of the Bureau of the Census.

[2] Thomas W. Taylor, Florida’s territorial lighthouses, 1821-1845: a legacy of concern for the mariner (Allandale, Fla. 1995) 132. Whitehead appended to his sketch the following note: “Ten Miles from Key West the nearest inhabited land. The Light is kept by Mrs Rachel [sic] R Flaherty who with her sister are the only inhabitants of the Island (which is not more than 400 yds in circumference) with the exception of a seaman who has charge of a boat and catches fish for a livelihood who occasionally visits them.” Memorandums of peregrinations by land & water, Volume 2, facing page 87, in the collections of the Key West Art & Historical Society. Barbara Mabrity was for a time Rebecca Flaherty’s counterpart on Key West: named by Whitehead keeper of the Key West light on her husband’s death in 1832, she served in that capacity for a remarkable thirty-two years.

[3] Stephen R. Mallory, Diary and reminiscences, 1861-1872, 2:170, Southern Historical Collection no. 02229, University of North Carolina Special Collections. 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 (hereafter “Childhood and youth”); page 30 of the transcription contains the reference.

[4] “Memorial to Congress by inhabitants of Key West,” 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) 134-137. Another petitioner, Joseph Merriman, was probably the “Merriman Joseph” of the census, a free man of color with two female dependents, one a girl under 10. Boston, Ruby and Merriman were all aged 24-35 in 1830. William A. Whitehead also signed the petition, although he was not yet a permanent resident.

[5] In 1856, attorney William R. Hackley recorded that he “drew up a memorial from Lucy Boston to allow her children and grandchildren to come from Nassau. Fontane [presumably Philip J. Fontane, Monroe County’s representative in the state House of Representatives] will try to get a law passed, to that effect.” William R. Hackley, Diary, in Goulding Collection, Special Collections, Florida State University Libraries, Tallahassee, MSS 0-128 (hereafter Hackley, Diary), entry of 13 November 1856.

[6] It appears that these laws were unevenly enforced, and unpopular with some in the community. A presentment by a Monroe County grand jury in 1834 complained of “the introduction of free negroes and mulattoes into this county, particularly from the British West India Colonies which is done almost daily and with impunity, and in utter disregard of the laws.” Key West (Fla.) enquirer 3 January 1835 2:2. Publication in the Bahamas of Florida’s prohibition on admittance of free Blacks led the Key West Enquirer to comment, “The Legislative Council has thus deprived our wreckers of their most useful seamen.” The enquirer (Key West, Fla.) 8 August 1835 3:1. Cf. Judge James Webb’s verdict in the case of William Delancy, and Whitehead’s publication of the Act of Congress that exempted seamen of color from the ban of 1803: The enquirer 2 May 1835 3:2-4.

[7] Key West (Fla.) gazette 23 May 1832 3:3-4.

[8] Key West gazette 1 August 1832 1:1.

[9] The property designated as Ruby’s, Lot 4 in Square 25 on Whitehead’s map, was granted to “Cassimir Ruby” by Pardon C. Greene in a deed of 26 October 1829. A year later, Greene mortgaged another Whitehead Street property, Lot 2 in Square 39, to “Felix C. Ruby.” Monroe County Deed Records, Monroe County Public Library, Key West, Book A:210-211, 258-259. In November 1830 “a negro man of the name of Ruby” was charged with trying to set fire to Ellen Mallory’s house; the British vice-consul on Key West, objecting to his confinement on the grounds that Ruby “claimed to be a subject of the British government,” was himself jailed and fined for contempt of court. Hackley, Diary, entry of 25 November 1830. Cassimir Ruby and Felix C. Ruby may have been one and the same: Cassimir, detained with four other men in 1835, ostensibly for violating the territorial ban on migration of free persons of color, signed the detainees’ petition “Felix C. Ruby”: John W. Stewart et al. to the Hon. James Webb, Judge of the Superior Court for the Southern District of Florida, 1 May 1835, Monroe County Public Library, Key West.

[10] Key West inquirer 26 December 1835 3:4.

[11] Key West inquirer 30 January 1836 3:2.

[12] Key West gazette 27 April 1831 3:3.

[13] Key West gazette 25 May 1831 3:2. “I read the Funeral Service at the grave W.A.W.”: marginal note in Whitehead’s copy. Stanard’s “disease was the consumption to which he has been subject for many years and some other diseases. … He was buried under some trees about 150 yards East of the Light House.” Hackley, Diary, entry of 13 May 1831.

[14] Key West (Fla.) register, and commercial advertiser 19 February 1829 2:4, 23 April 1829 2:4. “Hymenial,” Key West enquirer 6 December 1834 3:3. See “Childhood and youth” 24-25.

[15] John Whitehead, Washington, 29 May 1829, to Martin Van Buren, Secretary of State, in Territorial papers XXIV 221-222.

[16] Key West gazette 12 (13 as printed) October 1831 2:1-2; 19 October 1831 2:1; 26 October 1831 2:3-4; 2 November 1831 2:2-3.

[17] Key West gazette 9 November 1831 2:4.

[18] Key West enquirer 3 January 1835 2:1; The enquirer 11 April 1835 2:1-2.

[19] Key West register 31 December 1829 4:3.

[20] Key West gazette 21/28 March 1831 2:3; 11 April 1832 2:3.

[21] “Childhood and youth” 29; W. A. Whitehead, Reminiscences of Key West no. 9, published in Key of the Gulf (Key West, Fla.) in May or June 1877, on which was based the edition of Thelma Peters, “William Adee Whitehead’s Reminiscences of Key West,” Tequesta: the journal of the Historical Association of Southern Florida 1:25 (1965) (3-42) 27-30. The letterbook manuscript copy at the New Jersey Historical Society, part of Manuscript Group 734, supplies some variant readings. References to Peter’s text appear in parentheses thus: (Peters 28).

[22] Strobel’s “special grievance” according to Whitehead “was that the Deputy Collector had struck off from the Marine Hospital roll the name of a man whom, having been seen walking about the town was thought well enough to be discharged, without first consulting him, he being at that time in charge of the hospital patients.” Reminiscences of Key West no. 9 (Peters 28). Complaints against Pinkham also included allegations that he sold property stolen during a salvage operation, then charged duty on it: see “Look at this,” Key West gazette 5/8 September 1832 2:1-2.

[23] B. B. Strobel, “To the public,” Key West gazette 5/8 September 1832 2:2-3.

[24] “Childhood and youth” 29-30; Reminiscences of Key West no. 9 (Peters 28).

[25] “Childhood and youth” 43-44.

[26] When the census was conducted in summer 1830, Whitehead was in the north; he left the Keys permanently in 1838, two years before the next enumeration. The census did find another William Whitehead, known to be the master of a wrecking vessel and in 1830 a non-citizen resident of the Keys.

Images: 1) Monroe County: Map of Florida according to the latest authorities (detail), from A new American atlas, designed principally to illustrate the geography of the United States of North America… (Philadelphia: A. Finley, 1826), page 13 (detail), David Rumsey Map Collection. 2) Sand Key light: W. A. W[hitehead], Memorandums of peregrinations by land & water recorded for my own amusement, vol. 2nd, facing page 87, Key West Art & Historical Society. 3) Map of the Town of Key West, together with the island (detail), Harvard Map Collection, Harvard Library.

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