Sound crazy? Maybe, but secession has been proposed several times over the years.

In 1969, when writer Norman Mailer and columnist Jimmy Breslin ran for mayor and city council president on the Independent Party ticket, one of their ideas was to make New York City the 51st State.

And in 2003, City Council member Peter Vallone introduced a bill that would allow the city to cut the state loose—because upstaters were sucking out too much of the city’s revenue.

But perhaps the closest New York City came to actually becoming sovereign was in 1861. The Civil War was pretty unpopular here because the city stood to lose so much money, since New York manufacturers wouldn’t be able to continue importing cotton from the South.

So Mayor Fernando Wood (looking dapper at left) proposed that the city form a city-state called Tri-Insula—that’s Latin for “three islands”—composed of Manhattan, Long Island, and Staten Island.

With Tri-Insula its own entity separate from the Union and the Confederacy, the Southern cotton trade wouldn’t have to stop.

In the end, it was just too radical an idea even for New Yorkers to accept.