George Washington, like all men in the American colonies, was entrusted with the estates of the women and children in his family.

Not only shall a father be concerned with the future of his child, but he should also secure a financial well-being for it. A parental guardian, like the non-biological father of a boy, owes the child this same fiduciary duty. This duty, if not upheld, can be grounds for the removal of custody of a child. Therefore, the father should act responsibly and err on the side of conservatism rather than act according to the frivolities of emotion and love by which a father might otherwise spoil his child. Such was the mindset of George Washington when rearing his teenage step-son, Jacky Custis.

George Washington married Martha Washington, the widow of Daniel Parke Custis, a wealthy Virginia socialite. It was the custom in those days for the new husband of a widow to manage the widow’s inherited estate with the caveat that the new husband have no right to sell any of the estate. That right was reserved by the legal owner, the inheriting widow, in this case, Martha Washington. The same went for the inheritance of the Martha’s son, John Parke “Jacky” Custis. George Washington had to responsibly manage the Custis estate once he married Martha.

The teenage Jacky Custis inherited a relatively unprofitable lot of land from his father. It was hardly fertile and grew an insignificant amount of tobacco cash-crop. In fact, it mostly just incurred expenses as it employed approximately 60 slaves who had to be furnished, fed, and cared for. While Washington managed this land, Jacky spent most of his time chasing the trivial pursuits common in the 1760s, such as hunting, shooting, and horse racing.

When Jacky’s tutor, Johnathon Boucher, ardently suggested that Jacky go on a Grand Tour of Europe, the matter of financial responsibility became the deciding factor. George Washington had no desire to prevent the boy from taking the trip. He recognized the benefits the boy could reap from it, like “to perfect his education,” and to develop him as a gentleman. However, he hoped that the promise of such a trip would help the boy focus on his school rather than those fanciful pursuits of his. Nonetheless, the matter of cost was of chief concern.

George Washington learned from his friends and peers that such a trip regularly costed over 1500 sterling pounds a year, the highest denomination of currency used in the Colonies. To give an idea of how much money that really was at the time: 1210 sterling was the cost of an 1806-acre plot of good land near Mount Vernon that Washington purchased a few years prior. Jacky’s estate only provided him an allowance of approximately 500 sterling pounds a year. Therefore, Washington considered it to be as imprudent as it was unfeasible to send Jacky on such an expensive trip that Jacky alone could not afford. Washington would not expend his own money unless Jacky improved his performance in school.

This matter was frequently deliberated between Washington and the tutor Boucher. Washington urged Boucher to take Jacky back to school as soon as possible because he was observing in Jacky a sluggishness in conduct and a lack of motivation to study, which grew worse the longer Jacky spent away from school. The matter was never decided and Jacky never took the trip.

Jacky eventually received full control of his inheritance a few years later when he turned 17 in 1773. He would marry a year later, to the surprise of George and Martha Washington who thought he and his fiancé were too young.

Washington’s efforts to raise Jacky largely failed. Jacky was more concerned with his high-born status than the work it took his fathers to achieve such status. His business dealings, including a foolish, high interest loan to buy a plantation for himself and his young family, nearly bankrupted him. His lack of education and discipline made him a poor delegate in the Virginia House of Burgesses as he could neither intelligently handle political matters nor even show up on time to meetings. The young Jacky Custis died only a few years later in 1781 at the age of 26 due to typhus, which he contracted in a war camp at the siege of Yorktown during the Revolutionary War.