Pinback button promoting William McKinley for president and Theodore Roosevelt for vice president, 1900. The Whitehead and Hoag Co., Newark, New Jersey.
When Col. Theodore Roosevelt returned from Cuba, hero of his Rough Riders cavalry unit, Republican Party bosses in New York recognized a golden opportunity and tapped him to run for governor in 1898. There were doubts, however, about his loyalty. Roosevelt had been a New York State assemblyman in the 1880s who had built a reputation for charting his own course politically. As governor, he became an energetic reformer, passing progressive legislation and rooting out graft wherever he found it, and the bosses now badly wanted to be rid of him.
They saw another golden opportunity in 1900. There would be a vacancy on President McKinley's reelection ticket, thanks to the timely death of Vice President Hobart. Roosevelt was drafted to run, and the McKinley-Roosevelt ticket handily swept the field in November. Historically, the vice presidency was a dead end job, a sinecure with no real power that usually concluded a politician's career. For Roosevelt, however, it would readily serve as a means of advancement to higher office, for barely six months into his second term, President McKinley was dead at the hand of an assassin. Instead of a maverick in the governor's mansion at Albany, he now resided in the Executive Mansion at Washington, what the 42-year-old President Roosevelt, in a symbolic break with the past, would officially rename the White House. The rest is history.
This pinback from 1900 pictures McKinley, the last 19th century president, and Roosevelt, the first 20th century president.