The year is 1757. George Washington is 25 years old and is engaged in the French-Indian War. Near Charlottesville, Virginia, Thomas Jefferson’s father, Peter, has just died at age 49 at his home in Shadwell. Young Thomas is only 14 years old -- the third of ten children and the oldest son. While his father was not well educated, he made sure that Thomas received schooling and had books to read. Yet, with his father gone, what would he decide to do with his future? Years later, speaking of this time in his life, Jefferson wrote to his eldest grandson (Thomas Jefferson Randolph): "When I consider that at fourteen years of age the whole care and direction of myself was thrown on myself entirely, without a relative or a friend qualified to advise or guide me, and recollect the various sorts of bad company with which I associated from time to time, I am astonished that I did not turn off with some of them, and become as worthless to society as they were. From the circumstances of my position, I was often thrown into the society of horseracers, cardplayers, foxhunters, [as well as] scientific and professional men … and many a time have I asked myself … "Well, which of these kinds of reputation should I prefer--that of a horsejockey, a foxhunter, … or the honest advocate of my country's rights?" As we know, young Thomas made his choice to develop his reputation, not as not a “horsejockey, cardplayer or foxhunter,” but as an “honest advocate of his country’s rights.”
In his short biography of George Washington, Founding Father, Richard Brookhiser, states that “Washington and his contemporaries thought of reputation as a thing that might be destroyed or sullied…reputation was held to be a true measure of one’s character—indeed, in some sense identical to it.” In 1814, at the age of 70, Thomas Jefferson reflected on Washington’s character:
I think I knew General Washington intimately and thoroughly; and were I called on to delineate his character, it should be in terms like these. His mind was great and powerful, without being of the very first order; his penetration strong, though, not so acute as that of a Newton, Bacon, or Locke; and as far as he saw, no judgment was ever sounder … His integrity was most pure … He was, indeed, in every sense of the words, a wise, a good, and a great man … it may truly be said, that never did nature and fortune combine more perfectly to make a man great, and to place him in the same constellation with whatever worthies have merited from man an everlasting remembrance …We knew his honesty … I felt on his death, with my countrymen, that ‘verily a great man hath fallen this day in Israel.’
While partisan animosities had splintered their previous friendship, Jefferson’s opinion of Washington’s virtues had not diminished. Perhaps his keen observations of Washington’s character traits may be indicative of those that Jefferson himself sought and valued in his own life: a penetrating mind, sound judgment, wisdom, goodness, integrity, and honesty. We may presume that to him, as to Washington and their contemporaries, one’s character and reputation were not to be trifled with and truly mattered in the grand scheme of things.
In the founding generation, a man’s character, or his virtuous characteristics and behavior, meant both private and public virtue, civic and religious. America’s first dictionary published by Daniel Webster in 1828, defined “Virtue” as “moral goodness; the practice of moral duties and the abstaining from vice, or a conformity of life and conversation to the moral law. In this sense, virtue may be, and in many instances must be, distinguished from religion. The practice of moral duties from sincere love to God and his laws is virtue and religion. In this sense it is true, that virtue only makes our bliss below.” This contemporaneous definition fittingly describes Jefferson’s own pursuit of virtue. His moral philosophy was founded on an understanding of each person’s innate sense of right and wrong, or conscience. This moral sense, said Jefferson in a letter to Peter Carr, “may be strengthened by exercise … [and] is as much a part of man as his leg or arm.” In the same letter, Jefferson stated that “[you should] lose no occasion of exercising your dispositions to be grateful, to be generous, to be charitable, to be humane, to be true, just, firm, orderly, courageous &c. Consider every act of this kind as an exercise which will strengthen your moral faculties, & increase your worth.” He also believed that the simple combination of morality and common sense was more likely to be found in the average man, such “a ploughman,” than in the highly educated man, such as “a professor,” who are “led astray by artificial rules.”
 Concerning the character trait of honesty (without which no man’s reputation is honorable), Jefferson wrote, “He who permits himself to tell a lie once, finds it much easier to do it a second and third time, till at length it becomes habitual; he tells lies without attending to it, and truth without the world's believing him. This falsehood of the tongue leads to that of the heart, and in time depraves all its good dispositions.” (Letter to Peter Carr, September 19, 1785). Jefferson also said, “honesty is the first chapter in the book of wisdom.” (Letter to Nathaniel Macon, January 12, 1819).
 Letter to Peter Carr, August 10, 1787, ME 6:257.