Laughter drowned out the shouts of encouragement as a tall, lean bolt of lightning exploded across the flat open grass, focused on the finish line a quarter mile ahead. At the start, his rival, heavier and more slow-footed, was given a lead of half the course’s distance. This advantage was compromised, however, by the weight of the man he carried on his back! Amidst cheering and merriment, this friendly rivalry played out in 1787 on the North Carolina frontier, and offers significant insight into the subject of this biography. Young Andrew Jackson challenged his friend and fellow law student Hugh Montgomery to race. This common amusement in rural America was frequently enhanced by wagering on the contest. Amazingly, and to the surprise and delight of a number of the bettors, Jackson won by two yards.