At the age of fourteen, the sandy-haired, pockmarked lad of the Waxhaws found himself alone in the world. The death of his relatives had made him heir to a portion of his grandfather’s estate in Carrickfergus; but the property was tied up in the hands of an administrator, and the boy was in effect both penniless and homeless. The memory of his mother and her teachings was, as he was subsequently accustomed to say, the only capital with which he started life. To a natural waywardness and quarrelsomeness had been added a heritage of bitter memories, and the outlook was not bright.
Upon one thing the youth was determined: he would no longer be a charge upon his uncle or upon any one else. What to turn to, however, was not so easy to decide. First he tried the saddler’s trade, but that was too monotonous. Then he undertook school-teaching; that proved little better. Desirous of a glimpse of the world, he went to Charleston in the autumn of 1782. There he made the acquaintance of some people of wealth and fell into habits of life which were beyond his means. At the race track he bet and swaggered himself into notice; and when he ran into debt he was lucky enough to free himself by winning a large wager. But the proceeds of his little inheritance, which had in the meantime become available, were now entirely used up; and when in the spring the young spendthrift went back to the Waxhaws, he had only a fine horse with elegant equipment, a costly pair of pistols, a gold watch, and a fair wardrobe—in addition to some familiarity with the usages of fashion—to show for his spent “fortune.”
One other thing which Jackson may have carried back with him from Charleston was an ambition to become a lawyer. At all events, in the fall of 1784 he entered the law office of a certain Spruce Macay in the town of Salisbury, North Carolina; and, after three years of intermittent study, he was admitted to practice in the courts of the State. The instruction which he had received was not of a high order, and all accounts agree that the young man took his tasks lightly and that he learned but little law. That he fully sustained the reputation which he had gained in the Waxhaws is indicated by testimony of one of Macay’s fellow townsmen, after Jackson had become famous, to the effect that the former student had been “the most roaring, rollicking, game-cocking, card-playing, mischievous fellow that ever lived in Salisbury.”