Marble Hill
New York, New York
In most cases, a despited territory is an island, and Manhattan is no exception. There’s a small part of Manhattan that’s physically part of the Bronx, but both of the boroughs have been playing tug of war for the past century over it.
It started in 1895, when this northernmost neighbourhood was separated from the island of Manhattan by the construction of the Harlem Ship Canal, turning it into an island itself. Then in 1914, the Harlem River was filled in on the north side of Marble Hill, connecting it to the mainland and the Bronx. While it’s physically connected to the rest North America, Manhattan still tries to call dibs on it from time to time, and the Bronx tries to smack them down. This leads to some interesting jurisdictional dick-size comparisons hand waving.