The Everything Theodore Roosevelt Book
from California a few years earlier; and Edith.
    She may not have been on the ticket, but Edith was against TR’s involvement based on two issues: They were planning a wedding in Europe less than a month after Election Day, and he would have to take office only a few weeks after that if he won, which would cut into their honeymoon. Despite her objections, TR ran—and lost. At least he did not lose Edith.

Henry George ran as the United Labor Party candidate in the 1886 New York City mayoral campaign. He was best known for his support of the land value tax, a.k.a. “single tax,” on land and the founder of “Georgism,” the philosophy that everyone owns what he or she creates, but that everything found in nature—primarily land—belongs equally to all humanity.
    The race was an eye-opener for TR. His opponents overshadowed him and his supporters practically ignored him. He understood that, and he did not expect to win. He was scheduled to sail to Europe with Edith only four days after the election.
    TR had purchased tickets under the name of Merrifield for a trans-Atlantic voyage aboard the Eturia , which was scheduled to leave New York on November 6. That morning, he and “Mrs. Merrifield,” actually his sister Bamie, boarded Eturia in disguise. They had spent the previous night writing engagement announcements and wedding invitations. He figured that by the time the announcements and invitations reached their destinations, he would be at sea.
    TR was right about the outcome of the election, but he had no intention of leaving politics. Many people believed that someone like TR, who came from one of the city’s aristocratic families, should not be involved in politics. What could he know about the severe economic depression, high levels of unemployment, political graft, and labor disorders that were plaguing the city, they wondered? As a result, many Republicans crossed party lines and voted for his opponents. Perhaps that was for the best as far as TR’s career was concerned.

The Mayoral Race
    Almost all the city’s aldermen were under indictment for taking bribes, workers were extremely underpaid for the long hours they toiled—sometimes as many as sixteen hours a day—and labor unions were agitating for power.

Significantly, 207 separate unions, representing 50,000 local employees, banded together as the Central Labor Union and got behind George, as did labor leader Samuel Gompers, who had sparked TR’s interest in politics just a few years earlier. TR did not have anywhere near the name recognition George did or empathy for the city’s residents, according to his opponents.
    Hewitt represented the most powerful political machine in New York—and the United States. He was a seasoned campaigner who had served five terms in the U.S. House of Representatives. (He resigned during his fifth term to take over his mayoral duties.) Strangely enough, he shared some characteristics with TR that George could not emulate.
    Hewitt, like TR, was rich and a philanthropist. That helped him, but it worked against TR. Hewitt had worked his way to millionaire status starting with a public school background, whereas TR had been born with the proverbial silver spoon in his mouth. In truth, by 1886 TR’s personal wealth was nowhere near Hewitt’s.

There were 219,992 votes cast in the 1886 New York City mayoral election. The breakdown, according to the November 14, 1886, New York Times: Hewitt (90,552); George (68,110); Roosevelt (60,435); Wardwell (582). The final tally left 313 votes unaccounted for, but the missing votes were not enough to sway the outcome.
    In the long run, Hewitt’s age (he was sixty-four years old), government experience, family connections, ties to a political machine, and promise that he was the only candidate who could save New York City from “socialism, communism, anarchism, nihilism, and revolution” were too much for TR to overcome.
    TR campaigned enthusiastically, but lost badly in the

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