What, Sir, is the use of a militia? It is to prevent the establishment of a standing army, the bane of liberty. Whenever governments mean to invade the rights and liberties of the people, they always attempt to destroy the militia, in order to raise an army upon their ruins.

He frequently communicated with other Massachusetts opponents of British policy including Samuel Adams John Adams Mercy Otis Warren and others. The painting was reproduced on the reverse of the two-dollar bill beginning in 1976. Although he speculated in depreciated Continental bills of credit (the IOUs at issue) there is no evidence he participated in large-scale speculation that attended the debate when it took place in 1790 and he became a major investor in the new bank.

During his second term the legislature approved new state senate districts that led to the coining of the word "gerrymander"; he lost the next election although the state senate remained Republican. Gerry was at first opposed to the idea of political parties and cultivated enduring friendships on both sides of the political divide between Federalists and Democratic-Republicans. He was one of three men who attended the Constitutional Convention in 1787 but refused to sign the United States Constitution because it did not then include a Bill of Rights.