This cartoon entitled "The Gerry-Mander" was first published in The Boston Centinel in 1812. It depicted a congressional district in Massachusetts designed to favor the Democratic-Republican candidate over the Federalist candidate. This cartoon coined the term "gerrymandering".
By Elkanah Tisdale (1771-1835) (often falsely attributed to Gilbert Stuart) (Originally published in the Boston Centinel, 1812.) [Public domain], via Wikimedia Commons