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Authors: Joseph Wheelan

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Whatever his motives, Lear openly criticized Eaton's scheme to build an insurgency around Hamet Karamanli and drive his brother Yusuf from Tripoli. “... I should place much more confidence in the continuance of a peace with the present Bashaw, if he is well beaten into it, then I should with the other, if he should be placed on the throne by our means.”
 
Tobias Lear had been Barbary's consul general for nearly two years. In his portrait from that time, he appears as an oval-faced man with large, intelligent eyes and a pointed nose, clad in an army officer's coat, with a sedentary man's double chin. Lear often signed his correspondence “Colonel Lear,” proud of the rank Washington had given him during the Quasi-War with France. Washington, picked to command American ground forces, had named Lear his chief aide. Washington's army never took the field because the French didn't send an army to North America; the Quasi-War was fought at sea. Lear, however, signed his correspondence with his titular rank for the rest of his days.
He had devoted nearly his entire adult life to America's first family. In May 1786 the twenty-four-year-old Harvard graduate became George Washington's personal secretary and moved to Mount Vernon. Over the years, he became more of a family member than employee, particularly after making two of Washington's nieces his second and third wives, after his first died in Philadelphia's 1793 yellow-fever epidemic. As Washington's personal secretary, he handled correspondence, kept the family books, tutored the children, attended to Washington's varied business
interests, and dined every day with the family. He followed Washington to New York and Philadelphia when he became president.
At the beginning of Washington's second term, Lear struck out on his own, hoping to make a fortune through business and land speculation in the new capital city being built on the Potomac. He continued to act as Washington's business agent and sent him letters full of shrewd observations whenever he traveled. He also served as a director of the Potomack Company, organized by Washington and other businessmen to make the Potomac River a commercial pipeline to the heartland.
In December 1799, when the ex-president was dying of pneumonia at Mount Vernon, it was Lear who held his hand as he uttered his last words. (Washington told him not to put him in his burial vault until he had been dead three days, just for good measure.) Washington's will granted Lear rent-free tenancy for life at Walnut Hill Farm at Mount Vernon.
Yet, during all his years with George Washington, the repository of all the early United States' hopes, Lear was an observer, not a participant. Only once had he been a central player in his own right, and it had not redounded to his credit. Lear was blamed for the sensational disappearance of all the correspondence between Washington and Jefferson from 1797 until Washington's death two years later.
This was significant because Washington and Jefferson, fellow Virginians and Revolution patriots and friends for twenty years, had quarreled bitterly in 1797 and had exchanged several sharp letters. The disappearance of the copies undoubtedly made of Washington's letters to Jefferson and Jefferson's replies to Washington—while they were in Lear's possession—erased all traces of their angry exchange. Of course, none of the letters
turned up among Jefferson's papers because Jefferson's indiscretion had caused the rupture in their friendship in the first place, and the letters would have reflected poorly on him.
Jefferson, as did all Republicans, had vilified the Jay Treaty as a dirty piece of bootlicking by Anglophile Federalists. But unfortunately, Jefferson also vented his unhappiness in a blistering letter to Philip Mazzei, a former Monticello neighbor who had moved back to his native Italy. Through circuitous means, the letter unexpectedly found its way into print in the United States, and a storm erupted. The catalyst was Jefferson's thinly veiled reference to Washington, already a national icon, in the line, “men who were Samsons in the field & Solomons in the council, but who have had their heads shorn by the harlot England.”
Jefferson was disconcerted by the letter's publication, and Washington was furious. The breach that opened up between the two old friends wasn't helped by the accusations that flew in a subsequent exchange of heated letters. Only one survived Washington's death. In it, Washington expressed outrage over the “grossest and most invidious misrepresentations” of his administration's actions.
John Marshall, the first U.S. Supreme Court chief justice and the era's leading Federalist, discovered the strange gap in the men's correspondence when he took possession of Washington's papers in early 1801—from Lear, who had them to himself for a year. (Marshall based his masterful, four-volume Washington biography on these papers.) Lear said nothing to Marshall about the gap. Later, however, he acknowledged to Alexander Hamilton and others that he had destroyed letters Washington would never have wished to be made public.
But Lear might have acted for more selfish reasons than concern
for Washington's posterity. In
The Checkered Career of Tobias Lear,
historian Ray Brighton suggests there might have been a quid pro quo between Lear and Jefferson, who was running for president when Lear had possession of the papers. Publication of the letters very likely would have cost Jefferson the election, which he only managed to win on the thirty-sixth ballot in the U.S. House, after an Electoral College tie with Aaron Burr.
Lear and Jefferson had been friends since Jefferson's years in Washington's Cabinet, and Lear privately agreed with Jefferson's Republican views. He also needed a job that paid well, for his unlucky business speculation in the new capital had plunged him deeply into debt.
While it will never be known whether Lear and Jefferson had an agreement about the letters, Jefferson and Madison made sure Lear had a government job for the rest of his short, eventful life. (In 1814 Lear saved the Army's records when the British burned Washington. Two years later, he committed suicide.)
Within weeks of Jefferson's inauguration, Lear was appointed to his first job: consul to Santo Domingo. This was a coveted post, because opportunities abounded for getting rich in the West Indies trade. But Lear happened to arrive during the tumultuous aftermath of a slave rebellion and was expelled months later when French troops invaded.
As consul general for the Barbary States, he had hoped to establish a reputation and accumulate wealth, but the war had afforded him a chance for neither.
 
 
 
Early in 1805, Lear temporarily moved from Algiers to Malta so he could be close to Tripoli if an opportunity arose for a parley. He was eager to negotiate a peace, no matter what Eaton and Hamet
accomplished. The shortest distance to his goal was through Barron, who lay helplessly ill in Syracuse. Lear shuttled between Malta and Syracuse, making sure nothing—such as a naval offensive—upset his plan for a diplomatic settlement. He also systematically undermined Hamet's credibility with Barron. Eaton had so favorably impressed the commodore during their Atlantic crossing that at the beginning of 1805, Barron had pledged to cooperate with Eaton and Hamet and to restore Hamet as bashaw. Lear, aware that if their desert expedition dethroned Yusuf his own efforts would inevitably become expendable, or, at best, secondary, inexorably turned the commodore against Hamet and Eaton.
He had to tread carefully because he didn't want to come across to Barron as a crank, and because no one really knew what the president had agreed to when he met with Eaton the previous year. So he took cover in others' opinions, such as those of Nissen, who assayed the damage caused by Preble's attacks as “very inconsiderable.” And there was Bainbridge, who in his letters from captivity clearly opposed any action that would jeopardize his crew's safety or extend its captivity. Bainbridge also thought little of Eaton's expedition, or of Hamet, a “poor effeminate refugee ... who had not spirit enough to retain his situation when placed in it,” and who had “wandered an Exile far from Country, Wife & Children for more than 8 years without disturbing the Regency of Tripoli.” Bainbridge, who had plenty of idle time to ponder the Tripoli situation, had concluded that blockading was futile. As he saw it, America had three options: bombard Tripoli and seek terms immediately; capture the city with an army; or “abandon us entirely to the hard fate which serving our Country plunged us into.”
Lear also pounced on Richard Farquhar's bitter complaints
about Eaton after Eaton expelled him from Alexandria for embezzling expedition funds. “He writes to the Commodore that Mr E. is a madman,” Lear gleefully told Captain John Rodgers, a friend from his brief Santo Domingo consulship. “He has quarreled with the Ex-Bashaw &c &c &c, We are in daily expectation of more authentic accounts from that quarter; but I make no calculation in our favour from that source.” Lear never identified the source, and nothing more came of the matter.
By the spring of 1805, as Eaton's expedition was pushing deep into eastern Tripoli, Barron was beginning to sound like Lear on the subject of Hamet: “I confess that my hopes from a Cooperation with him are less sanguine than they were.” He attributed his changed outlook to recent information “from persons well acquainted with the Bashaw [Hamet] of his Character & Conduct.” In other words, Lear. No report from Eaton had yet arrived to change Barron's thinking about the overland campaign. But Lear's influence over Barron—who, although invalided, still clung to his authority as regional commander to conduct the war as he saw fit—was nearly absolute after the commodore's long months of illness. Barron confessed to Lear that his newfound lack of confidence in Hamet, coupled with the expedition's cost and overly ambitious goals, “compel me to relinquish the plan.”
Barron also anticipated every conceivable drawback and obstacle whenever he weighed bringing his naval force into action against Tripoli. An attack was ill-advised without gunboats, the only vessels that could safely navigate the shallow harbor, and he had been unable to procure any from Naples or Venice. He was unsure when ten being built in the United States would arrive. The enlistment period of Preble's squadron began expiring in early autumn, “an important period in our Arrangements.” Three
frigates needed refitting. Under the circumstances, Barron made no plans to bring his large squadron against Tripoli.
The situation was rich in its circuitous irony. With Barron disinclined to launch a naval attack, Lear had to depend on the very force he was trying so hard to discredit—Eaton and Hamet's army, encamped on the heights above Derna—to force Yusuf to sign an honorable peace for which Lear could then claim credit.
XV
DERNA AND PEACE
Dorna, Saturday April 27, 1805
I shall see you tomorrow in a way of your choice.
—William Eaton in a letter to Mustifa Bey, governor of Derna
 
My head or yours.
—Mustifa Bey
 
 
 
H
idden in the sparsely wooded hills overlooking the city, Eaton, Hamet, and their officers studied the white buildings and palm trees fringing the harbor. With upwards of 10,000 inhabitants, Derna was Tripoli's second-largest city. Bananas, dates, grapes, melons, oranges, and plums flourished in the city's orchards and irrigated gardens, whose cultivation dated to the 1493 arrival of the Moors exiled from Spain. To the north, the Mediterranean's sparkling blue waters stretched to the horizon. Mussolini would call Derna “the pearl of the Mediterranean,” but other visitors, immune to its charms, were oppressed by its isolation and the air of desolation bestowed by the endless sea and the nearby hills.
Derna was the administrative and military hub of Cyrenaica, Tripoli's distant eastern province and traditionally its most restive, as a result of its 500-mile remove from the capital across stretches of hostile territory. Its nomadic Berber and Bedouin tribesmen
remained largely outside Yusuf's authority. Hundreds of them had rallied to Hamet's standard, swelling his ranks to 1,000 fighting men. Derna itself was only nominally in the bashaw's camp and just as liable to switch sides.
 
After Eaton, Hamet, and their army occupied the hills overlooking the provincial capital on April 26, Eaton scouted the enemy defenses with a small mounted force and gathered intelligence from dissident city chiefs. What he learned was not reassuring. The city was defended by at least 800 government troops, a shore battery of eight 9-pounders and a 10-inch howitzer on the terrace of the governor's palace. A third of the populace was firmly in Yusuf's camp, and most of them lived in the city's southeast district. They had fortified that area of the city by cutting firing ports in the walls of the homes. In the northeastern sector, defenders had thrown up breastworks tying in with the buildings. The chiefs warned Eaton that he would have difficulty dislodging the troops because they knew that if they held out, Yusuf's 1,200 cavalry and infantry would relieve them in a day or two. This information made Eaton eager to attack as soon as possible, but disheartened Hamet. “I thought the Bashaw wished himself back to Egypt,” Eaton noted drily in his journal.
After reconnoitering Derna and seeing to his army's disposition for the night, Eaton joined Lieutenant Isaac Hull on the Argus, and they mapped out a battle plan for the next day. Eaton spent the night on the brig and awakened the following morning with the fatalistic thought that this day might well be his last. Before boating ashore to rejoin his army, he left instructions for doling out his personal effects in the event that he was killed in battle. Hull would get his cloak and smallsword; Captain James Barron,
his Damascus saber; his stepson, Eli Danielson, his gold watch and chain; and Charles Wadsworth, his estate executor back in America, was to receive the rest.
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