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One of the first mentions of a connection between Taft as a public figure and Christmas goes back to his time as the military governor of the Philippines. Taft held the office during a period of civil strife amid battling factions on the islands, in the aftermath of the Spanish-American War. Each year, leading up to the winter holiday, Taft would review the long list of military and political prisoners and issue pardons or reduced sentences to those individuals he deemed most deserving. Prisons were badly overcrowded during this violent period, and Taft was reported to be generous when it came to issuing the pardons. One of his most famous and controversial instances of clemency concerned the case of a priest who had brutally killed the leader of the war-torn city of Taylay during a violent uprising. Taft reduced his death sentence to one of 20 years in prison.
When Taft was elected President in the election of 1908, he did so with very little support from the South. Despite this, Taft intentionally chose the city of Augusta, Georgia as the location of his family’s Christmas vacation. Taft wanted to show that he held no grudge against those who had voted against him and that he would represent the interests of all Americans. His family spent part of their time at the residence of a Mr. Hack, who had been a prominent supporter of William Jennings Bryan. (Taft had defeated Bryan a month earlier in the presidential election.) Mr. Hack presented the Taft family with a native holly tree as a gesture of goodwill. The evergreen mistletoe on the tree was said to represent a much hoped-for era of good feelings between the political parties and the regions.
In a letter to his sister-in law, Taft wrote that the family was greatly enjoying their stay in Georgia, complaining only that his children hardly spoke and when his wife Nellie spoke, it was generally to criticize his efforts at cabinet-making. He also commented that Nellie had adapted much better and was far more enthusiastic than he to have become a part of Washington’s elite political society. Many people believed that Nellie Taft was the one who convinced her husband to follow Theodore Roosevelt’s plan for Taft to pursue the presidency in 1908, as opposed to doing what Taft wanted: an appointment to the United States Supreme Court.
During his time in office, Taft was known for his generous nature, which was apparent in the scope and number of Christmas gifts he sent out. Taft did not limit his gifts to family and friends, his Christmas list often numbered in the hundreds. He would send out presidential Christmas cards to accompany the gifts. Often, his aides would have to scramble to acquire more White House cards as the list grew in length. Taft would usually spend several days going Christmas shopping. Among his favorite items to send were books and jewelry, and he always made his own selections. On each of the books he sent, he would write a personal sentiment inside the cover, giving these objects a lasting historical value.
Taft would also present Christmas gifts to all of the White House clerks. He also sent a Christmas turkey to all married White House employees – usually just over 100 turkeys. He would also give a personal holiday remembrance to each of the Secret Service men assigned to protect him. According to press reports, a 35–40 pound prize turkey, delivered by Horace Vose, the poultry king of Rhode Island, graced the table of the first family every Christmas, along with "Aunt Delia's goodies." The president's Aunt Delia Torrey of Millbury, Massachusetts, always sent "Nephew Will" an eagerly anticipated package of apple pies, jellies, and jams made from fruit grown on the Torrey property.
President and Mrs. Taft enjoyed Christmas shopping in downtown Washington along with holiday crowds. It is said that on occasion Taft would slip away from his Secret Service detail to stroll through the city, often with his friend and aide Archibald Butt. On Christmas Eve in 1911, the president and first lady secretly left the White House on foot to call on friends as a surprise. When the Secret Service discovered their absence, there was widespread panic. Chief John Wilkie and his men scurried all over town searching for them. Eventually, President Taft returned to the White House smiling broadly with Mrs. Taft holding his arm.
In 1909, Taft's son Robert, was nineteen and was a junior at Yale. His daughter Helen, seventeen, was a student at Bryn Mawr. Only their youngest child, Charles, eleven, lived with his parents year round at the White House. In 1912 while President and Mrs. Taft were away on an inspection of the Panama Canal, Robert and Helen hosted the family celebrations and held a Christmas tree party in the Blue Room for their young cousins. The huge tree decorated with thousands of electric lights, set a precedent for decorating a tree on the State Floor for guests. Although absent, President and Mrs. Taft still provided gifts for friends and each employee of the White House received a fat turkey, a practice began by presidents in the nineteenth century.