Samuel, the eldest of his own brothers, and his junior by but two years, though constantly corresponded with, was not a favorite.  He seems to have had extravagant tendencies, variously indicated by five marriages, and by (perhaps as a consequence) pecuniary difficulties.  In 1781, Washington wrote to another brother, “In God’s name how did my brother Samuel get himself so enormously in debt?” Very quickly requests for loans followed, than which nothing was more irritating to Washington.  Yet, though he replied that it would be “very inconvenient” to him, his ledger shows that at least two thousand dollars were advanced, and in a letter to this brother, on the danger of borrowing at interest, Washington wrote, “I do not make these observations on account of the money I purpose to lend you, because all I shall require is that you return the net sum when in your power, without interest.”  Better even than this, in his will Washington discharged the debt.

To the family of Samuel, Washington was equally helpful.  For the eldest son he obtained an ensigncy, and “to save Thornton and you [Samuel] the expence of buying a horse to ride home on, I have lent him a mare.”  Two other sons he assumed all the expenses of, and showed an almost fatherly interest in them.  He placed them at school, and when the lads proved somewhat unruly he wrote them long admonitory letters, which became stern when actual misconduct ensued, and when one of them ran away to Mount Vernon to escape a whipping, Washington himself prepared “to correct him, but he begged so earnestly and promised so faithfully that there should be no cause for complaint in the future, that I have suspended punishment.”  Later the two were sent to college, and in all cost Washington “near five thousand dollars.”

An even greater trouble was their sister Harriot, whose care was assumed in 1785, and who was a member of Washington’s household, with only a slight interruption, till her marriage in 1796.  Her chief failing was “no disposition ... to be careful of her cloathes,” which were “dabbed about in every hole and corner and her best things always in use,” so that Washington said “she costs me enough!” To her uncle she wrote on one occasion, “How shall I apologise to my dear and Honor’d for intruding on his goodness so soon again, but being sensible for your kindness to me which I shall ever remember with the most heartfelt gratitude induces me to make known my wants.  I have not had a pair of stays since I first came here:  if you could let me have a pair I should be very much obleiged to you, and also a hat and a few other articles.  I hope my dear Uncle will not think me extravagant for really I take as much care of my cloaths as I possibly can.”  Probably the expense that pleased him best in her case was that which he recorded in his ledger “By Miss Harriot Washington gave her to buy wedding clothes $100.”