Although he was popular, President Roosevelt knew he had never been elected to the post in which he now served. Traditionally, Republicans favored big business while Democrats supported progressive candidates who advocated reform. At first, it was unclear whether Roosevelt would win his Republican Party's nomination. However, the president was successful, winning not only the nomination, but also a landslide victory that stunned the incumbent president himself.

Although politics kept the president occupied much of the time, his family life filled the remaining gap. Roosevelt was the father of six rambunctious children, some of whom slid down White House staircases on metal trays. His oldest, Alice, was a bit of a handful. She loved to shock people by smoking in public, keeping a pet snake, and behaving in other ways that were unconventional for women of that time, including betting on horses at the racetrack. Teddy Roosevelt reportedly said, “I can be president of the United States, or I can control Alice. I cannot possibly do both.”

The children no doubt obtained much of their charisma from their father, who was also a great supporter of racial equality. He was the first president to invite an African-American to dinner at the White House when he dined with Booker T. Washington, principal of the Tuskegee Institute in Alabama.

Unfortunately, in spite of all of his fine attributes, Roosevelt's strength in keeping his promises proved to be a mistake in at least one case. During the campaign of 1904, he vowed not to seek re-election in 1908. But when the end of his second term rolled around, this young, still-ambitious man wanted to stay in the post in which he excelled. He felt he could not — he had to keep his promise. Yet because of his great popularity, Roosevelt helped to pick his successor. William Howard Taft won the election of 1908, taking office the following year.

The Taft administration was fairly lackluster, although it continued the previous administration's progressive policies, carrying trustbusting further than Roosevelt had. Taft also took advantage of many new technological innovations, for example, he was the first president to buy automobiles for the White House. Though good-natured (he was teased about his weight of more than 300 pounds), he had trouble filling the shoes of his predecessor. In the end, Taft served only one term, but went on to become the tenth chief justice of the United States (and the only person ever to hold the highest offices in both the executive and judicial branches).