DOCKS, custom house and town had all vanished from sight when the revenue cutter rounded Whitehead Point. At once, the south beach came into view, its carbonate sands sparkling in the light of a bright April morning. Soon the whole island would drop below the horizon, as the cutter Marion made its way gently over the reef into Hawk Channel and the broad Florida Strait.
The interests of the island engaged the cutter’s lone passenger for most of his journey, first by sea to Charleston, then by land to Washington and points further north. But it would be half a year before William A. Whitehead laid eyes once more on Key West.
Much had changed at the custom house in the fifteen months since Whitehead took charge as collector. In January 1831 he’d found, besides a boat’s crew of four men, only Thomas Eastin, “a man twice my age,” holding the position of inspector. With “both the business of the office and my own comfort” in mind, Whitehead gave priority to the immediate appointment of a deputy. During his long sojourn in the North, his choice to fill that position turned out to be of greater moment than he could have foreseen.
David Coffin Pinkham is thought to have been a Massachusetts native, very possibly from Nantucket, but the earliest definite record shows him practicing law in Louisville. Like many of his class and generation, Pinkham didn’t limit himself to one professional pursuit, but also entered the political arena and its confederate trades of newspaper publishing and printing. In 1825, he left Kentucky for Pensacola, where he restarted his legal practice and was twice elected to Florida’s territorial legislature. Three years later he quit the Panhandle for Key West, one of an influx of lawyers drawn to the Keys after Congress authorized a Superior Court for the south of the peninsula.
Pinkham had entered his late 30s when Whitehead named him deputy collector of the customs. Although “a man of gentlemanly bearing and fair education” he had, the collector admitted, no prior commercial experience. He “wrote an indifferent hand, and knew nothing of business forms or accounts.” Whitehead professed some surprise “that under these circumstances we should have harmonized so well,” but he’d no doubt settled on Pinkham as someone who, although a good deal older (Whitehead was just 21), would respect his expertise and acknowledge his authority. A faithful lieutenant would be indispensable, especially during an absence as long as Whitehead’s in 1832.
Once in the North, at a remove of a thousand miles or more, Whitehead could keep tabs only by means of sporadic correspondence from his deputy and others on Key West, or scraps of news reprinted in northern papers. That spring and summer were not a quiet time in the Keys, but the opening of Judge James Webb’s court in May settled at least one protracted controversy, the salvage case of the ill-starred brig Halcyon. Whitehead’s deputy, still a practicing attorney, had argued the case on behalf of the salvors, the notorious wrecking captain Jacob Housman at their head. An initial award for their services, 56.25% of the proceeds from sale of the vessel–held up as emblematic of the corrupt proceedings for which the wrecking economy of the Keys was widely known–was knocked down on appeal to just 25%.
In response to the worldwide cholera epidemic, Key West city fathers imposed a quarantine in April on vessels arriving from ports known to be affected. Then, in July, they made the restrictions much tighter: quarantine and a steep fine were required of anyone boarding or leaving an incoming vessel before inspection by the health officer of the port. This prohibition complicated the enforcement of the revenue laws with which Pinkham was entrusted, and for which Whitehead ultimately was responsible. And the deputy’s task was made more difficult still by the authorities’ declining to require health inspections after sunset. This exposed the port to a different sort of epidemic, one of after-hours smuggling.
Pinkham promised to cooperate with the city insofar as possible, even allowing the port physician use of the revenue boat. But if a vessel entered with a foreign cargo when this officer was not on hand, its goods could easily be offloaded and delivered without paying duty. One night in August, Pinkham learned that such a vessel had arrived from Havana and was anchored about 20 yards from the wharf. The health inspector being at home about a mile away, a customs inspector (Pinkham or another) approached in a small boat: “having ascertained that there was no sickness on board he proceeded to discharge his duty.” The next day, the authorities charged this officer with violating the ordinance, and fined him $300.
On the 13th and 14th of August, a fierce gale battered the Keys. “We apprehend,” announced the next day’s Key West Gazette, “that many vessels have been wrecked or injured by it.” Wrecking captains were thus alerted to the prospect of profitable work relieving disabled craft and recovering their cargoes. Whitehead, though far away, knew well that the harbor would bustle with schooners, sloops and fishing smacks striking out for the Reef and returning with cargo and articles to be sorted, entered, appraised and charged duty. Such a flurry of activity would entail long days for his deputy and for the inspectors, weighers and gaugers working under him.
Clearly there would be much to catch up on when Whitehead set foot again in the custom house. But nothing could have prepared the collector for the document awaiting him when he returned to his desk in October:
We the undersigned beg leave to represent that during your absence, those who have been obligated to transact business at the Customs House, have with very few exceptions, been subjected to great inconvenience and unpleasant feelings in consequence of the arrogance and insolence of D. C. Pinkham your Deputy.
Every species of petty tyranny has been manifested in the discharge of his official duties, indicative of a bad heart, and a weak head.
He has neither the integrity, patience or temper, talent for or knowledge of business, so indispensably necessary for a public officer.
He has suffered himself invariably to be actuated and guided in the transactions of his official duties by his personal feelings and private concerns.
We are prepared to set forth these facts by the evidence of numerous witnesses.
Subscribing to this manifesto were four Key West citizens whom Whitehead knew well. And while the four went on to assure him of their personal esteem, and their confidence in his “willingness to do Justice to the feelings and for the injuries of those who have been aggrieved,” they attached a promise that, “should this means fail,” they wouldn’t hesitate to apply for Pinkham’s removal to the Secretary of the Treasury, Whitehead’s superior.
With their presentment they submitted names of a half dozen distinguished gentlemen, Judge Webb’s at the top of the list, who they said were prepared to speak of “the public opinion, feeling and sentiment” regarding the deputy’s conduct during his superior’s six-month absence. Whitehead obligingly wrote to all six, to learn particularly the feelings of “those persons who have business in my office. The investigation,” he declared, “however painful it may be, is a duty which I conceive I owe to myself and to all parties concerned.”
The quartet of David Pinkham’s accusers were all prominent if not universally respected figures in the island’s early development. Thomas Eastin, lone inspector of the customs when Whitehead arrived in 1831, had something of a checkered past. Once the editor of Key West’s first newspaper, he’d made an unsuccessful bid for the collector’s job, and gotten into a row with a previous deputy collector. At the time of Whitehead’s return from the North, Eastin had just quit the inspector’s position for that of U.S. marshal. Henry S. Waterhouse, a bookish, eccentric physician and druggist and the island’s first postmaster, also worked now and then as temporary inspector of the customs, as well as weigher, gauger and measurer of imported articles. Oliver O’Hara, Key West’s first mayor, served mercantile houses both foreign and domestic as a commission agent, and was Great Britain’s vice consul on the island. O’Hara and Pinkham had been on opposite sides in the Halcyon case. Finally there was Benjamin B. Strobel, another doctor; he launched and operated the island’s second newspaper, the Gazette, alongside his duties as surgeon to the army post, town health officer and port physician. As had O’Hara, Strobel found David Pinkham his adversary in a suit at law, a case more delicate and personal, and apparently still pending: Strobel sued Jacob Housman and his wife for alleging that he revealed the identity of an unmarried patient on whom he’d performed an abortion. Pinkham was the attorney for the defense.
If the reputations of these four men preceded them, the nature of their grievances seemed to Whitehead at first general and rather opaque. He got little clarity, at least in writing, from the six leading citizens he consulted. Three of them conceded that Pinkham was a very unpopular figure in the community, but on what basis they couldn’t say.
The four complainants, meanwhile, began assembling evidence in the form of affidavits to place before Whitehead. In his capacity as justice of the peace, Henry Waterhouse took one sworn statement from O’Hara and two from Strobel. According to O’Hara’s statement, the deputy had improperly denied him a bond for duties on certain imported goods. One of Strobel’s affidavits accused Pinkham of speaking to him in a “haughty, overbearing and insolent manner” about replacing a recently deceased lighthouse keeper. Strobel’s other statement complained of the peremptory discharge of a sailor, until then in Strobel’s care, on the pretext that the hospital fund for sick and disabled mariners administered by the collector had been exhausted.
The statements of the other two accusers had more directly to do with their employment under Pinkham. Thomas Eastin cited three specific altercations–including one over his boarding an arriving vessel with the health inspector in a boat–and claimed the deputy had used violent or ungentlemanly language toward him at each of these times. The charges leveled by Henry Waterhouse were filled with passion, rhetorical flourish and prolixity, but so devoid of details that Whitehead had to insist on specifics:
What duties has he called upon you to perform, for which he has not furnished you with proper data?
In what manner has he illtreated and abused you for not having performed such duties?
In what manner has he as Deputy Collector attempted to villify [sic] your character as a “subordinate agent of the Customs”?
How have you been prevented from obtaining a “just remuneration” for duties performed, from Mr. Pinkhams failing in his “promises” & what were those promises?
Towards whom has he conducted himself in your presence in his capacity of Deputy Collector “in a haughty, tyrannical, overbearing and abusive manner”? Please to specify names and time.
Oliver O’Hara’s complaint, a part of Eastin’s and the entirety of Waterhouse’s were rooted in the aftermath of the violent storm that August. Transatlantic commerce had suffered, much as Strobel’s Gazette predicted, relegating large shipments of foreign goods to the wharves and warehouses of the Keys. The American ship Shepard, making its way from Havana to Hamburg laden with 2,450 boxes of sugar, had gone ashore in the upper Keys, while a British vessel, Eliza Plummer, headed from Kingston to Liverpool with Jamaican rum, sugar and Madeira wine, foundered in sight of the many watchful eyes onshore at Key West.
Deputy Pinkham, facing not only this incoming cargo but chains, cables, anchors and furniture from the lost Eliza Plummer, much of it having to be weighed and all of it subject to duty prior to its imminent sale, pressed Thomas Eastin and Henry Waterhouse into service. According to the affidavit of the latter, when Pinkham discovered him weighing items not requiring it, he was berated “for not knowing which parcels were and which were not to be weighed.” The deputy also withheld from him appraisers’ returns needed to calculate damage. And by stopping him in the middle of his work, Pinkham had made it plain, without actually saying so, that he considered Waterhouse incompetent or untrustworthy. “If this was not plainly & incontrovertibly on his part an ‘attempt to villify my character’,” said the temporary inspector, “I do not either understand the meaning of a plain action, or the import of terms.”
Waterhouse and Eastin further accused Pinkham of denying them a “just remuneration” for their services, having first promised them the weighing of Shepard’s entire cargo of sugar, then trusting them only with the few boxes that were damaged, assigning the bulk of it to others. Eastin wound up his deposition by saying that Pinkham was “obnoxious” to many in Key West, and that he’d heard “general complaints” of the deputy collector’s “tyranny and hauteur” from the seafaring population.
Whitehead was not long in digesting these and other charges before he presented them to his deputy for a response. Pinkham, preliminary to giving an answer, chose to address the matter of his alleged unpopularity by gathering testimonials to his professionalism and willing service to merchants and ship masters. They were of one mind in their satisfaction with Pinkham’s performance, regarding any differences of opinion as resulting from his strict compliance with the law. Some even vouched for the propriety with which he treated his subordinate officers.
In a lengthy letter to Whitehead, Pinkham then addressed the complaints of each of his accusers in turn. He had stricken the injured sailor from the hospital rolls based on Benjamin Strobel’s admission that he no longer needed care but was kept on because he had no other means of support. It was “to correct the cupidity of Doctors & nurses” that Pinkham monitored the state of marine hospital patients. The sailor in question was, in fact, returned to the rolls when Pinkham judged that he wasn’t yet healed, and eventually received paid passage off the island.
Appointed agent for Eliza Plummer and its cargo, Oliver O’Hara had already given bonds for nearly $18,000 in duties when he declared he would sell the ship’s entire cargo at auction. When he presented another bond for $205, and would not postpone the sale until Whitehead’s return, Pinkham insisted those duties be paid in cash, which O’Hara would not do. Pinkham stood by his judgment: “had I taken his bond, the charge of partiality and personal feeling would have been much more applicable to me than at present.”
The more elaborate complaints of his sometime assistants the deputy collector was compelled to treat at greater length. But the substance of his defense came down to the one man’s inattention, the other’s duplicity, and the insubordination of both. On Eastin’s watch, “a great deal of petty smuggling was carried on” in which at times he seemed to be complicit, and he openly defied an order of Pinkham’s, leading to his suspension from the inspector’s job. Found weighing articles that he knew didn’t need to be weighed, Waterhouse was certainly trying, “by trick and artifice,” to increase his fees, and he declined to follow directions in the weighing of the sugar, producing returns that Pinkham regarded as “worse than useless.” To the charge of attempting to “vilify his character as a subordinate agent of the Customs,” Pinkham stated that he must plead guilty if it was done in the course of preventing Waterhouse from illegally enlarging his fees.
In a summation such as one would expect from a defense attorney, Pinkham adverted to the ill-will and baseness of his attackers. During most of the time the collector was absent, leaving his deputy “a very difficult and arduous duty to discharge,” they had operated to injure and discredit him. In what he wryly termed this “honorable employment” of theirs, “Dr. Strobel was the principal actor, and Waterhouse the willing instrument….” The former, having no other knowledge of custom house business than what he was paid for hospital patients, seemed annoyed mainly “that I did not keep them there as long as he wished.” Waterhouse had proved to be a man “full of low cunning,” and recently had been indicted for theft. Eastin’s “gross negligence & incapacity,” he predicted, would surely manifest itself in his new position as marshal. And O’Hara was “a man vain, proud & overbearing in his private character, entirely ignorant of the most ordinary knowledge or duties of a merchant, & with vanity equal to his ignorance.”
The deputy collector’s job was no doubt a coveted position. When Whitehead first advertised it, there had been eight applications in the first twenty-four hours. Upon David Pinkham’s selection, it was recalled, there was “great uneasiness” in the community, “particularly the commercial & mercantile part of it,” which only increased when it became known that Whitehead would be leaving on a visit to the North. It’s curious, therefore, that among the nearly 20,000 words about Pinkham’s case filling 85 foolscap pages in the National Archives, most of them laboriously transcribed from originals by Pinkham’s successor Stephen Mallory, there’s hardly a whisper from anyone taking the side of Pinkham’s accusers. It’s difficult to know how to regard this near unanimity of satisfaction with a man who was thought so unpopular. But William Whitehead had chosen him, and would stand by him. The high esteem in which Whitehead was held may have done much to mitigate the defects of his deputy.
Indeed, Whitehead saw the complaints of Pinkham’s accusers for what they were. “I have not been unmindful that two of you,” he wrote, “have repeatedly & openly expressed to me the personal dislike & enmity that you have felt towards him, long before any of the acts now complained of occurred.” Eastin and Waterhouse, in the collector’s absence and at the instigation probably of Strobel, if not of O’Hara as well, had allowed their personal hostility to Pinkham to be transformed into something more malignant. Whitehead fully endorsed his deputy’s actions concerning hospital patients, supported his ruling on the custom house bond, and agreed with the censure of his subordinates. If any of the complainants wished to continue seeking redress for their grievances, he felt the right course would be “to apply to the party from whom the injuries have been received.”
One detail in Henry Waterhouse’s charges, however, remained to be clarified: a mention of “perquisites” he and Eastin expected from gauging the rum and wine saved from the ship Eliza Plummer. It appeared Waterhouse and others were claiming the right to set aside some of the imported liquors for their own consumption, or to sell. Pinkham had questioned this right, he said, giving in when certain reputable merchants informed him that it was customary at Key West and elsewhere. But Whitehead notified both Waterhouse and Pinkham of his “unqualified disapprobation” of the practice, regretting that in his absence “it was done so openly and as if it was a right possessed by the officers.” This prompted the deputy to prepare a further statement to the effect that he had received no liquor other than samples of wine for revenue purposes.
It would fall to Whitehead to report that his deputy left this statement unsworn, for much more had to be resolved than a minor question of embezzled liquor. Pinkham was restored to his post, but Benjamin Strobel, who had shut down the Key West Gazette and closed his medical practice, remained a presence on the island and an annoyance to the deputy collector. “The Doctor, whose complaints were least in consequence if at all,” so persisted in his abuse of Pinkham that “nothing would do but he must seek redress….” Pinkham, who knew nothing of firearms, challenged Strobel to a duel.
This turn of events can be variously explained, but it’s very likely that Strobel, dissatisfied with Whitehead’s refusal to dismiss his deputy, had gone over his head and complained to Washington. Otherwise the Treasury Department would have had little knowledge of the whole affair.
The doctor and the deputy met by appointment before daybreak on 23 March 1833, on the south beach, Key West’s usual “field of honor.” At first fire Pinkham collapsed, a ball lodged in his breast. His friends carried him home, where he lingered for almost three weeks before expiring.
On the day of Pinkham’s death, Whitehead received a letter from Treasury concerning the charges against him. He replied with the news that Pinkham was no more, forwarding his deputy’s answer and his own settlement of the matter, with the wish that, “as a satisfaction to his friends and to myself,” the department would indicate whether he had proceeded appropriately. In June, the department fully affirmed his decision, and notified him that none of the complainants should be employed by the custom house in future.
Benjamin Strobel left the island soon after the duel, it is believed for good, so it seems strange to find from him anything like a posthumous vindication of his enemy. Yet here is what he wrote in the Charleston Courier that summer:
… great antipathies will exist against public officers, among those, whom it is their duty to bring to justice. This hostility has been repeatedly manifested by charges preferred to the heads of department at Washington. In many cases these charges are secretly preferred, and it is not at all times in the power of an officer to meet them as they should be met. … My object is to urge the importance and necessity (whether an Officer be right or wrong) of affording him a fair chance of vindication. More especially, when the peculiar difficulties of his situation are taken into consideration. Where such causes exist, a ready pretext will be found in the most trifling incident upon which to ground the most serious charges, and an efficient Officer might be dismissed on account of animosities created by a faithful discharge of his duties.
Whitehead would have had good cause to doubt Strobel’s sincerity here, but the opinion of custom house work offered to Pinkham by another Key West figure–a complicated character in his own right–harmonized well enough with Whitehead’s own that he chose to repeat it in part:
One thing I am certain of, that any man in the same office as yourself who is strictly correct in all its details, can not fail to be unpopular for a time with some part of the community, but in the end he will become more popular when it is seen that he acts only from a sense of duty to his government.
Popularity among officers of the Customs is what I have never seen in any country, & I apprehend that our Government will always prefer to have strict, faithful & correct Custom house officers to popular ones.
Copyright © 2026 Gregory J. Guderian