Louis Menand in The New Yorker:
Mayor of New York City is famously a dead-end job. The last New York mayor to win higher office was John T. Hoffman, and that was in 1868. He became governor. Every mayor since then has found the way up barred. And, for some, the way up turned into the way down.
The mayors are often a little surprised by this reversal of fortune. The assumption seems to be: If I can govern there, I can govern anywhere. This may or may not be true. What is true is that New York City’s mayors have had a hard time getting non-New Yorkers to vote for them. After all, you’re not likely to be elected President of the United States by promising to make the country more like New York. You basically have to run against your own home town.
When John V. Lindsay, who was elected mayor in 1965 and became one of the country’s highest-profile politicians, ran for President, in 1972, he was forced to drop out after finishing fifth in the Florida primary, where he had counted on getting the votes of retired New Yorkers. He quit politics after a 1980 New York Senate bid, joined two law firms, and made regular appearances on “Good Morning America,” but health problems and the collapse of both firms nearly wiped him out. In 1996, an ally on the City Council arranged for this once charismatic and commanding figure to be given two essentially ceremonial appointments in city government just so he could have health insurance.