Thomas Woodrow Wilson was born near the end of December 1865, in Staunton, Virginia, to parents Joseph R. Wilson and Janet Woodrow Wilson. Interestingly, the exact date of his birth is not known for certain. When he was born, it was recorded in the family Bible that he was born at "twelve and three- quarters o'clock" at night on December 28. This was the date that Wilson himself used throughout his life. Thomas Woodrow was the third child of four and grew up with the nickname "Tommy", a name he eventually dropped after graduating from college.

Tommy's father, Doctor Joseph Ruggles Wilson, was a prominent Presbyterian clergyman and professor who hailed originally from Ohio and was of Scotch-Irish descent. His mother Janet "Jessie" Woodrow had a similar ancestry and was known for her beauty and charm. The two had met in Ohio during Joseph's brief stay as a teacher at a men's preparatory academy. After briefly working as missionaries in Canada, and after Joseph had served as a teacher and professor throughout the Midwest, they landed in Staunton, where Dr. Wilson became the minister of the local Presbyterian congregation in 1855. Throughout his life, Tommy looked on his father with only the deepest respect and love.

The church played a significant role in Tommy's upbringing, as the lessons he learned as the son of the prominent Presbyterian minister remained with him for the rest of his life. In the South during the mid 1800s, the Presbyterian church was among the wealthier Protestant denominations; Doctor Wilson's church was no exception, with its high ceiling, carpeting, and balconies for slaves. A good number of the Presbyterian preachers condoned and even advocated the practice of slavery, and many promoted the Southern lifestyle and social stratification. Many of these same preachers were among Joseph Wilson's closest and most trusted friends, and Tommy grew accustomed to listening to their discussions on religion, economics, government, and law.

Despite its stance on slavery, the rather conservative Church preached a strong sense of Christian morality, and Tommy learned to use these high standards as a lens to evaluate every word spoken and every action taken. Consequently, as an adult he viewed everything in terms of right and wrong, and more often than not based his decisions on the righteousness of his options. This trait was both an asset and a liability: it caused him to become one of the greatest reformers and Progressives, but at the same time eventually led to his downfall and nervous breakdown as President.

Shortly after Tommy's birth, the family moved again to Augusta, Georgia, in 1858 where Joseph accepted the position as minister of the local Presbyterian church. Tommy grew up much like every other Georgian boy; though he wore spectacles at an early age, he still managed to play baseball, hunt, and dance. A mischievous boy, he got into his fair share of scrapes as well, occasionally skipping school to plot and scheme and play with the other boys in a local gang of young ruffians known as the Lighthouse Club. Even though he spent all of his formative years in Augusta–from shortly after birth until nearly his middle teenage years–Tommy always prided himself on being born in Virginia. Throughout his life he considered himself to be a Virginian, and as a young man wanted nothing more than to enter politics and become a U.S. Senator from what he considered to be the greatest state.

Growing up in Augusta, Tommy also witnessed the effects of the Civil War on the South. His earliest memories of the war were times when he was far too young to understand much of what was going on. Legend has it that, while playing in his yard one day, he heard a passerby announce in disgust that Abraham Lincoln had been elected President. After the war ended in 1865, young Wilson remembered watching Union guards marching Jefferson Davis through town on his way to a prison. The entire South was hit hard by the devastating battles, Yankee raiding parties, looting, property destruction, poverty, and corrupt Northern government officials, not to mention the scores of thousands of lives the South lost in the struggle.

After the war ended, the Presbyterian church itself came under heavy attack from the state's new Reconstructionist government. The church was seen as the embodiment of the Southern ideal, especially since many prominent members of the Church–including Doctor Joseph Wilson–had decided to split from the main church when the war erupted and form the Southern Presbyterian Church. These experiences made a deep impression on the future President. Tommy was forever the Southerner, from these postwar experiences of hardship until the day he died. He thought like a Southerner, acted like a Southerner, and prided himself on being one.

Ironically, the man who would later become one of the most powerful and influential educators of his time never received any formal schooling until a late age, primarily because many of the schools in the South had been closed during the Civil War. He could not even recite the alphabet until he was nine years old and could barely read two years after that. As the son of a prominent professor and clergyman who was trained in theology, the classics, and rhetoric, among other subjects, Tommy's family thought him to be a dolt and lost cause when it came to book learning. Nevertheless, his parents loved him dearly and tried to educate him with more hands-on techniques. His father often took him to various places throughout the region to expose him to new environments and see new things. After each trip Tommy was made to describe exactly what he had seen in order to develop his communication skills. The family also studied parts of the Bible together every day and especially on Sundays.

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