Massachusetts: where the monster was born
Every map in this collection descends from one signature. In February 1812, Governor Elbridge Gerry of Massachusetts signed a redistricting law drawn to keep his party in the state senate.
One district curled through Essex County so grotesquely that a cartoonist gave it wings and claws, below, and the Boston Gazette christened the beast after its father: the Gerry-mander.
It worked, and it cost him. That April the opposing Federalists won the senate vote, 51,766 to 50,164, and took eleven seats to twenty-nine. Gerry himself lost the governorship the same day. The word has outlived them all.
Two centuries later, Massachusetts is the strangest ending the story could have: nine districts, below, all nine Democratic. Mathematicians, fittingly at a group founded to study gerrymandering, proved why the real map has no other side: the Republican third of the vote is spread so evenly across the state that in some recent elections no map, however it is drawn, elects even one Republican to Congress, and no map at all elects a red majority. The state that invented the gerrymander no longer needs one.
You are playing the Republicans in the one state where that is provably pointless. The theorem is about the real Massachusetts: on actual precincts, no map ever drawn, by anyone, gives Republicans five of the nine seats. But this board simplifies the state into a grid of houses, and on the grid a winning map does exist. So here is the side that should not exist: draw five red districts out of nine, in a state that has none.
Clinton 60.0%, Trump 32.8%. Massachusetts's 2016 presidential vote.

Elkanah Tisdale's 'Gerry-Mander' (Boston Gazette, 1812): the Essex County senate district, with wings and claws added. The cartoon named the practice.

Massachusetts today, shaded by the 2016 vote: nine districts, every one of them blue.