In 1873 Tommy entered Davidson College in North Carolina, the most distinguished Presbyterian college in the Carolinas. Several years earlier, the Wilson family had moved to the region after Doctor Wilson had accepted a professorship at the Presbyterian seminary in Columbia, South Carolina. Young Tommy performed well in his studies, but was not satisfied with the school. Like many colleges in the South, Davidson had been hit hard by the war and was still struggling to survive even almost a decade later. Young college students had to chop their own firewood, carry their own water, and eat whatever happened to be on hand. Tommy was not the most rugged individual and therefore left Davidson after his first year to return home to his family.

After taking a year off from school, Tommy–by this time known by his middle name, Woodrow– was accepted to Princeton University (then known as the College of New Jersey) and enrolled in 1875. Although he was not the most exceptional student at Princeton, he graduated with both academic and extracurricular honors. He enjoyed debating as a member of the forensics society, served as the editor of his college's newspaper, The Princetonian, and wrote for the Nassau Literary Magazine. He even published an article in an 1879 issue of the prominent International Review in which he demonstrated his scholarly abilities to think clearly and objectively. Woodrow was also a member of the Alligators eating club. He graduated in 1879, thirty-eighth in his class of slightly over one hundred.

Wilson's primary goal throughout his early life was to be a politician. He firmly believed that actions spoke much louder than words and that only through government could he truly affect and change society. It is not surprising, therefore, that after graduating from Princeton, the future President enrolled in the law school at the University of Virginia in 1879. Law has always been a common steppingstone on the path to legislative and administrative positions, and, although Woodrow actually found the study of law to be extremely boring, he endured the tedium of the program. He performed well in the classroom, but only truly enjoyed his work as a member–and eventually head speaker–of the Jefferson Debating Society. It was in this forum that he developed his knack for rhetoric and oration. Unfortunately, however, Wilson eventually withdrew from the law school in 1880 because of poor health.

Despite his withdrawal, Wilson nevertheless still felt that law was the best means to becoming a statesman. With the advice and consent of his father, therefore, he continued his studies at home with the goal of eventually practicing law. After passing the bar exam in 1882, he moved to Atlanta, which was then the most industrialized and promising Southern town. There, he established a law firm with Edward I. Renick, a former classmate at Virginia. Unfortunately for Wilson, the practice proved unsuccessful because clients were in short supply. Doubly painful was the fact that scores of other fresh law school graduates had had the same idea as Wilson and Renick; although Atlanta's population in 1882 was a mere 37,000, there were 143 lawyers in the city.

Despite his practice's failure, this time was not entirely a dismal one for Woodrow. He continued to study on his own, reading extensively in history, economics, and philosophy. He also practiced his public speaking skills whenever possible. That same year, he had the opportunity to testify before the United States Tariff Commission. The commission at this time was touring many of the larger Southern cities and towns, gathering evidence and taking testimony on the potential benefits and harm a new tariff would create. While most of the testimony came from struggling Southern businessmen who wanted a tariff, Wilson argued that a tariff would only hurt Southern consumers forced to purchase inferior products. Taking this idea a step further, he established a branch of New York's Free Trade Club in Atlanta. This early work on the issue of national tariffs and trade helped him years later as President.

By the time Woodrow Wilson arrived in Atlanta, he was nearly twenty-seven, but had thus far been unsuccessful in his romantic life. He was brilliant, but did not really look or act like it. He came from a prominent family, but was by no means wealthy, especially as a student and then as green lawyer with only a handful of clients. While at the University of Virginia, he fell deeply in love with Hattie Woodrow, his younger cousin who lived in nearby Staunton, the town of his birth. He proposed, but she refused.

Wilson had similar luck in his other attempts with women until in 1883 he met Ellen Axson of Rome, Georgia. Their meeting and courtship was ironic and rather serendipitous: while on one of his few actual business trips to Rome, Woodrow happened to see the young Ellen sitting in the back pew of the local Presbyterian Church during a Sunday service. She was the daughter of the church's minister–funny, sweet, and devilishly attractive according to Woodrow and all the other eligible men in Rome. He immediately tried to win her heart. Wilson extended his stay in Rome for several weeks to court her, and the two spent many hours together talking, reading, laughing, and enjoying picnics in the park.

Ellen reciprocated Woodrow's feelings, but was under self-imposed pressure not to pursue a serious relationship with him. Her mother had recently died, her father was near death, and she had taken it upon herself to care for her younger siblings. Woodrow returned to Atlanta somewhat crestfallen. The two briefly exchanged letters, but eventually stopped after a few months. By mere chance, however, both met several months later in a train station in North Carolina. Before Ellen's train left for Rome, Woodrow succeeded in winning her hand; the two were now engaged.

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