Eighteen-year-old Lewis Littlepage (1762–1802)1 arrived at Madrid in late October 17802 to study “law and politics” under Jay’s tutelage. Littlepage had been brought to Jay’s attention by Thomas Adams as a favor to Littlepage’s uncle, Benjamin Lewis, a Virginia planter.3 Littlepage had been tutored by the Reverend Thomas Hall (1750–1825) from 1774 to 1777, was a Nottoway scholar at the College of William and Mary from 1778 to 1779, and was a volunteer in the Virginia Artillery in the fated Matthew-Collier Raid of 1779.4 He came recommended as a person “whose talents and disposition merited better opportunities of improvement.”5 Jay took at face value Littlepage’s desire to engage in serious study and offered to provide him room and board at Madrid. He also cautioned Colonel Edward Fleming6 that his ability to finance his new charge was limited.7

Littlepage expected to enter an exciting and aristocratic social world, preferably in France, but instead found himself in the household of a sober minister who was unrecognized and snubbed by the Spanish court and inadequately financed by Congress. Bored with his studies, Littlepage informed Jay that he wanted to volunteer his services to the duc de Crillon, commander of the campaign to take Minorca from the British.8 Jay emphatically disapproved, since he had neither the authority nor the funds to sanction Littlepage’s military career.9 Ignoring these objections, Littlepage secured Crillon’s promise of a post as aide-de-camp, subject to Floridablanca’s approval, which neither Jay nor Crillon thought it likely he would obtain.10 Jay wrote Floridablanca on 17 June that although he withheld his consent from Littlepage’s venture, he would not restrain him.11

Much to Jay’s surprise, on 23 June, Floridablanca gave his permission.12 Jay, who was himself pressed for funds, reluctantly allowed Littlepage to draw enough money through Richard Harrison to cover his expenses until he joined Crillon, who had already left for Cádiz en route to Minorca. He instructed Littlepage, however, to draw further only if he was taken prisoner.13 Jay then informed Benjamin Lewis that Littlepage had joined Crillon and enclosed an account of his expenses.14 He also enclosed copies of his 15 June letter to Littlepage stating his opposition to the youth’s plans, his 17 June letter to Floridablanca, and his 24 June letter to Montmorin absolving himself from any further responsibility.15 Only his prior promises to Littlepage’s friends and his own good conscience kept him from relinquishing all responsibility for Littlepage.

On 3 July 1781 Littlepage requested that his credit be doubled, for although he was honored with the position of aide-de-camp, volunteers in the Spanish army were unpaid.16 Although Harrison declared Littlepage’s expenses justified, Jay questioned both the necessity of Littlepage’s employing a servant and his overly expensive journey from Cordova to Cádiz,17 and refused to honor a bill from Harrison for Littlepage in excess of the established credit.18 Littlepage continued, however, to importune Jay for further funds.19

At the end of the Minorcan campaign, Jay authorized Littlepage to draw on him for twenty guineas and instructed him to return to Madrid by the least expensive means.20 By the time Littlepage arrived in Madrid on 9 April, Jay had formed a permanent impression of him as a shallow, impetuous spend-thrift but felt unable to relinquish his responsibilities to his young ward.21 Before he left for Paris, he agreed to give Littlepage a room and a small allowance until March 1783. Despite Jay’s objections, however, Littlepage left Madrid in June 1782 to rejoin Crillon’s forces at the siege of Gibraltar.22

The Jay-Littlepage correspondence, only a small portion of which is published in this volume, reveals the growing rift between the pair. Typical of Littlepage’s inflated demands is an 8 October letter, enclosed in a 25 November 1781 letter. Jay’s lengthy reply of 26 October and his letter of 13 December document a rising irritation, not entirely bereft of understanding. Jay did not escape Littlepage’s importunities even when he went to Paris. Littlepage further inflamed Jay’s relations with William Carmichael by alleging that Jay had left him in Spain to spy on Carmichael and had given him a cipher in which to send his reports, something Jay vehemently denied.23 Later, in America, when Jay sought repayment of his advances to Littlepage, the two would have a notorious, politically embarrassing confrontation, during which the details of the dispute and much of the Jay-Littlepage correspondence was circulated in pamphlet form.24