On June 22, 1665, Thomas Willett was named the first mayor of New York. Like all good mayors, he was something of a coalitional candidate, one of the few men of rank acceptable to both the Dutch residents and the English invaders. One imagines that questions about authenticity and what it means to be a “real New Yorker” didn’t much exist then (since New York didn’t really either), but Willett had a good pedigree (he came over on the Mayflower) and, as all New York City mayors must do, kept up a good relationship with the governor, who in this case appointed him. Willett is a name lost to time now. The few mayors of New York who remain in our collective memory do so because they came to symbolize an era — the decadence of Jimmy Walker in the 1920s, the scrappiness of Depression-era Fiorello La Guardia, the benign neglect of the John Lindsay years, the punitive harshness of Giuliani Time, and the booming Bloomberg years.
On June 22, New Yorkers will vote in the primary that is all but certain to determine the next mayor, one who will immediately personify — and, to a large extent, shape — the city’s next era. For the first time, they will vote for not just one candidate but five, listed in order of preference. Ranked-choice voting was a longtime priority of good-government types who thought it would enable more candidates to enter the race, force them to campaign all over the city, and provide for a more congenial contest, since candidates would aim to be the second or third choice of their rival’s supporters.