In 1898, then-Colonel Theodore Roosevelt led his famous Rough Riders into battle in the Spanish-American War. One Rough Rider was Santa Barbara native and fellow Harvard alumni, Stanley Hollister. In 1900, Roosevelt became President of the United States. In 1903, he embarked on a 66 day, 14,000 mile train trip through 25 states, including California. He stopped in Ventura and toured the Sugar Beet Factory in Oxnard. He also made a timely visit at the Santa Barbara home of Annie Hollister, mother of Stanley Hollister—who died died five years earlier. When World War I broke out, Roosevelt offered to fight and was denied. His son, Quentin, took his place and died. How did this effect Roosevelt? We reveal these details in his personal letters.