1776: In his first year as mayor, David Mathews is accused of being part of a plot to kidnap George Washington. He is arrested for a short time but there's little evidence against him. When the Brits occupy New York later that year, he is restored to office; when they leave seven years later, he hightails it to Canada with other loyalists.
1844: Abram Hewitt, future mayor of New York, is shipwrecked on a return voyage from Europe with another future mayor, Edward Cooper (son of Cooper Union’s Peter Cooper). The two become so close that Hewitt marries Cooper’s sister—presumably one piece of the secret-pact-for-power puzzle they arranged during their “harrowing adventure”.
1898: Robert van Wyck, the first mayor of the consolidated city and the last with such a blatantly Dutch name, wins election against former Brooklyn mayor Seth Low, despite never delivering a formal speech during his campaign—because he just didn’t want to. Thanks for the votes, Tammany Hall! He is best remembered for copious scandals—such as an attempt to inflate the price of milk—and for being called a “dictator” by the state legislature. Oh, and awarding the first subway contract.
1906: George McClellan, Jr.—son of the bumbling Civil War general who later ran against Lincoln—wins reelection by defeating William Randolph Hearst, and serves out the rest of his term as the victim (duh!) of vicious newspaper attacks. It’d be like Bloomberg punching Rupert Murdoch in the face.
1910: William Jay Gaynor becomes the only New York City mayor to suffer an assassination attempt when a disgruntled former city employee shoots him in the throat. That’s why you don’t fire everyone once you take power! (See: Iraqi Army, ca. 2003.) The bullet stayed lodged in his gorge for three years, until he suffered a fatal heart attack on a Europe-bound steamer, likely caused by the, uh, slug in his throat, maybe?
1921: John Hylan is reelected largely because he opposes a state plan to raise subway fares by a nickel. We need you back, Johnny!
1929: Jimmy Walker, erstwhile Tin Pan Alley songsmith, is reelected, even though he spent almost 20 percent of his first two years outside the city and carried on a highly publicized extra-marital affair. (He eventually divorced his wife, Giuliani-style, and married his showgirl mistress, which apparently didn’t offend a plurality of voters. Those 20s sure did roar.)
1934: Fiorello La Guardia is elected mayor, even though he’s only five-foot-two. Even Bloomberg’s got a couple of inches on that.
1946: William O’Dwyer is elected mayor and declares “It’s a Great Day for the Irish.” It’s also their political death knell: New York won’t elect an Irish mayor again over the next 50 years.
1977: During the Koch vs. Cuomo campaign, posters pop up around the city encouraging voters to “Vote for Cuomo, Not the Homo”. The Cuomo campaign denies responsibility. Koch denies being gay. (Thirty years later, Time Out New York asks him straight up about his sexual orientation. He responds: “When was the last time you performed oral sex on your boyfriend?”) Koch supporters also accuse Cuomo of anti-Semitism, and throw eggs at his campaign’s cars.
2009: The Naked Cowboy drops out of the mayoral race—which also includes Mr. Burns—claiming that the only way to be taken seriously is to “show up in a suit and tie.” Rev. Billy runs in a bold blue suit and a clergyman’s collar in lieu of a tie—and, unfortunately, proves the guitar-slinging Times Square fixture correct when few take him seriously.