Where Washington wrote about Patsy with unfeigned affection, with Jacky he always seemed to bite his tongue and resort to euphemisms. Something about Patsy’s sweet simplicity he found irresistible, whereas Jacky’s feckless nature was to him intolerable. To Washington fell the thankless task of being the family disciplinarian, and he had to tread delicately in criticizing Jacky for fear of antagonizing his indulgent mother. Lacking the full legitimacy of a biological father, he found himself in a predicament as he tried to reform Jacky’s habits without running afoul of Martha. Though he might be the master of Mount Vernon, George Washington was far less powerful in the tiny emotional domain of his nuclear family.

Having been denied an adequate education, Washington went to inordinate lengths to educate his stepchildren properly. Starting in 1761, he hired a young, self-effacing Scottish immigrant, Walter Magowan, to tutor the children at home, and they were soon introduced to the Greek Testament and Latin poets and other things George Washington never learned. Toward the end of 1767 Magowan surrendered the post and returned to England, hoping to be ordained as an Anglican minister. In seeking a new teacher for thirteen-year-old Jacky, Washington contacted the Reverend Jonathan Boucher, an Anglican clergyman who ran a small academy for wealthy boys in his home near Fredericksburg. In his introductory letter, Washington described Jacky as “a promising boy” who was “untainted in his morals and of innocent manners,” but then he tipped his hand and confessed his “anxiety to make him fit for more useful purposes than a horse racer.”⁷ He was trying to be loyal to Jacky and frank at the same time, a tenuous balancing act he would perform for many years. A toadying character straight out of a Jane Austen novel, Boucher, with a tug of the forelock, answered in an unctuous manner: “Ever since I have heard of Mast[e]r Custis, I have wish[e]d to call him one of my little flock.”⁸ In short order, Washington rode off to Boucher’s school with Jacky, Jacky’s young slave Julius, and two horses.

At first Boucher expressed high hope for his young charge, and Washington placed an order in London for one hundred books, many in Latin. A transparently insincere fellow, Boucher laid on the flattery with a trowel, telling Washington what he thought he wanted to hear. His first letter described Jacky as a little angel, “a boy of so exceedingly mild and meek a temper” that Boucher worried he might be too artless, with “all the harmlessness of the dove” and none of “the wisdom of the serpent.” Of this little paragon, he concluded, “I have not seen a youth that I think promises fairer to be a good and a useful man than John Custis.”⁹

A year later, having discovered Jacky’s profligate nature, Boucher whistled a different tune. “You will rem[embe]r my having complain[e]d of Jack’s laziness, which, however, I now hope is not incurable,” he wrote to Washington.¹⁰ The reverend’s dismay steadily deepened: “The chief failings of [Jacky’s] character are that he is constitutionally somewhat too warm, indolent, and voluptuous.” He trembled for the fate of the Custis fortune: “Sunk in unmanly sloth, [Jacky’s] estate will [be] left to the managem[en]t of some worthless overseer and himself soon be entangled in some matrimonial adventure.”¹¹ Cognizant of the exorbitant wealth he would inherit, Jacky saw little need to apply himself to studies, which couldn’t help but distress his stepfather with his nagging work ethic.

In 1770 Jonathan Boucher became a rector in Annapolis, Maryland, and Jacky followed him there. Boucher’s scathing strictures on Jacky’s behavior came in private exchanges with Washington and probably weren’t communicated to Martha. Always concerned with Jacky’s health, she feared he would drown and urged Boucher not to let him swim too frequently. When Boucher devised an elaborate plan to chaperone Jacky on a grand European tour, Washington vetoed it as too expensive but probably suspected as well that Martha would never allow her son to travel for an extended period, especially on an ocean voyage.

In the end, Jacky became so uncontrollable that he started gallivanting about with friends after school and often spent the night elsewhere. Washington knew that Annapolis, with its horse races and theater, tempted his stepson with its many sinful haunts. “I would beg leave to request,” Washington told Boucher, “that [Jacky] may not be suffered to sleep from under your own roof . . . nor allow him to be rambling about at nights in company with those who do not care how debauched and vicious his conduct may be.”¹² No longer feeling obligated to flatter Master Custis, Boucher dropped all pretense. “I must confess to you,” he replied, “I never did in my life know a youth so exceedingly indolent or so surprisingly voluptuous. One would suppose nature had intended him for some Asiatic prince.”¹³ When Boucher suggested that the best way to control Jacky was to send his two horses back to Mount Vernon, Martha furiously refused her permission.

In dealing with his stepson, Washington betrayed the exasperation of a hardworking man coping with a spoiled rich boy. Jacky was spurning the very education that Washington had so sorely missed. Having never learned French himself, Washington told Boucher to teach it to Jacky: “To be acquainted with the French tongue is become a part of polite education and, to a man who has an[y idea] of mixing in a large circle, absolutely necessary.”¹⁴ Jacky never learned French or Greek or mathematics, as he was supposed to do.

One reason that Washington monitored Jacky’s education so narrowly was that he took seriously his role as guardian of the Custis estate. When he turned down Boucher’s request for the grand tour, he explained that its costs would exceed Jacky’s income, forcing him to draw down capital. This “might be deemed imprudent in me to allow without the sanction of the court, who are the constitutional guardians of orphans.”¹⁵ Jacky’s estate consisted of four plantations in New Kent County, 15,000 acres of land, somewhere between 200 and 300 slaves, and nearly 10,000 pounds in financial securities. One wonders how Washington felt about this devil-may-care stepson whose immense wealth easily rivaled his own.

In early 1773 Washington decided that the time had come to ship Jacky off to college. For Martha, William and Mary would have been the most desirable place, given its proximity to Mount Vernon, but Washington found the atmosphere at the Virginia school too lax. He wanted to send Jacky to the College of New Jersey (Princeton), but Boucher steered him instead to King’s College (predecessor to Columbia) in New York. Boucher argued that King’s was located in “the most fashionable and polite place on the continent,” and that he counted its president, Dr. Myles Cooper, as a personal friend.¹⁶ It is worth noting that Washington, taking a dim view of the moral climate in Virginia, wanted to educate his stepson in the North.

Once Washington decided in favor of King’s, Jacky introduced a fresh complication into the picture. This sexually precocious youth had spent considerable time wooing the opposite sex. “Jack has a propensity to the sex,” Boucher warned Washington, “which I am at a loss how to judge of, much more how to describe.”¹⁷ It was only a matter of time before Jacky became seriously involved with a young woman. In December 1771, when Jonathan Boucher moved again, this time to Prince George’s County, Maryland, he took along three students. One was Jacky and another was Charles Calvert, son of the wealthy Benedict Calvert of Mount Airy. Jacky courted Eleanor (Nelly) Calvert, Charles’s beautiful, dark-eyed sister, and by early 1773 had proposed to her. All this happened without the Washingtons’ knowledge. Shocked by the news, they tried, at a bare minimum, to slow things down. On April 3, 1773, Washington wrote an artful letter to Benedict Calvert, stating that he had heard of Nelly’s “amiable qualifications” and that “an alliance” with the Calverts would please him and Martha. He then went on to cite Jacky’s “youth, inexperience, and unripened education” as “insuperable obstacles . . . to the completion of the marriage.”¹⁸ Washington suggested that the marriage be deferred for two or three years until Jacky completed his education. In the letter, he distanced himself from Jacky and discreetly registered his disapproval without openly disavowing him. Benedict Calvert agreed that Jacky should spend two years at King’s College before marrying his daughter.