[2] Born into a wealthy merchant family, Gerry vocally opposed British colonial policy in the 1760s and was active in the early stages of organizing the resistance in the American Revolutionary War.

As one of the town's leading merchants and Patriots, Gerry played a major role in ensuring the storage and delivery of supplies from Marblehead to Boston, interrupting those activities only to care for his dying father.

[12] He was assigned to its committee of safety, responsible for ensuring that the province's limited supplies of weapons and gunpowder did not fall into British hands.

He was influential in convincing several delegates to support passage of the Declaration of Independence in the debates held during the summer of 1776; John Adams wrote of him, "If every Man here was a Gerry, the Liberties of America would be safe against the Gates of Earth and Hell.

He held these positions fairly consistently throughout his political career (wavering principally on the need for stronger central government in the wake of the 1786–87 Shays' Rebellion) and was well known for his personal integrity.

Gerry's opposition to popular election of representatives was rooted in part by the events of Shays' Rebellion in western Massachusetts in the year preceding the convention.

[31] He supported the idea that the Senate composition should not be determined by population; the view that it should instead be composed of equal numbers of members for each state prevailed in the Connecticut Compromise.

[40] During the ratification debates that took place in the states following the convention, Gerry continued his opposition, publishing a widely circulated letter documenting his objections to the proposed constitution.

[41] In the document, he cites the lack of a Bill of Rights as his primary objection but also expresses qualified approval of the Constitution, indicating that he would accept it with some amendment.

Henry Jackson was particularly vicious: "[Gerry has] done more injury to this country by that infamous Letter than he will be able to make atonement in his whole life",[41] and Oliver Ellsworth, a convention delegate from Connecticut, charged him with deliberately courting the Shays faction.

[57] He used the floor of the House to speak out against aristocratic and monarchical tendencies he saw as threats to republican ideals, and generally opposed laws and their provisions that he perceived as limiting individual and state liberties.

[63] Gerry joined co-commissioners Charles Cotesworth Pinckney and John Marshall in France in October 1797 and met briefly with Foreign Minister Talleyrand.

[65] Some days after that meeting, the delegation was approached by three French agents (at first identified as "X", "Y", and "Z" in published papers, leading the controversy to be called the "XYZ Affair") who demanded substantial bribes from the commissioners before negotiations could continue.

[67] Believing Gerry to be the most approachable of the commissioners, Talleyrand successively froze first Pinckney and then Marshall out of the informal negotiations, and they left France in April 1798.

[62] In response to the Federalist attacks on him, and because of his perception that the Federalist-led military buildup threatened republican values, Gerry formally joined the Democratic-Republican Party in early 1800, standing for election as Governor of Massachusetts.

[76] His opponent in these races, Caleb Strong, was a popular moderate Federalist, whose party dominated the state's politics despite a national shift toward the Republicans.

He preached moderation in the political discourse, noting that it was important that the nation present a unified front in its dealings with foreign powers.

The legislature also enacted "reforms" of the court system that resulted in an increase in the number of judicial appointments, which Gerry filled with Republican partisans.

However, infighting within the party and a shortage of qualified candidates played against Gerry, and the Federalists scored points by complaining vocally about the partisan nature of the reforms.

The shape of one of the state senate districts in Essex County was compared to a salamander[89] by a local Federalist newspaper in a political cartoon, calling it a "Gerry-mander".

The redistricting controversy, along with the libel investigation and the impending War of 1812, contributed to Gerry's defeat in 1812 (once again at the hands of Caleb Strong, whom the Federalists had brought out of retirement).

[93][94] The gerrymandering of the state Senate was a notable success in the 1812 election: the body was thoroughly dominated by Republicans, even though the house and the governor's seat went to Federalists by substantial margins.

[75] Gerry's financial difficulties prompted him to ask President James Madison for a federal position after his loss in the 1812 election (which was held early in the year).

He was viewed as a relatively safe choice who would attract Northern votes but not pose a threat to James Monroe, who was thought likely to succeed Madison.

[95] At that time the office of vice president was largely a sinecure; Gerry's duties included advancing the administration's agenda in Congress and dispensing patronage positions in New England.

On November 23, 1814, Gerry suffered a heart attack while visiting Joseph Nourse of the Treasury Department,[98] and he died soon after returning to his home in the Seven Buildings.

[102] The estate he left his wife and children was rich in land and poor in cash, but he had managed to repay his brother's debts with his pay as vice president.

Gerry is generally remembered for the use of his name in the word gerrymander, for his refusal to sign the United States Constitution, and for his role in the XYZ Affair and for his time as Vice President.

Early biographers, including his son-in-law James T. Austin and Samuel Eliot Morison, struggled to explain his apparent changes in position.

Biographer George Athan Billias posits that Gerry was a consistent advocate and practitioner of republicanism as it was originally envisioned,[103] and that his role in the Constitutional Convention had a significant impact on the document it eventually produced.