Born in Salem, Massachusetts, Timothy Pickering (1745–1829) graduated from Harvard College and practiced law before joining the Continental Army during the Revolution. He impressed General George Washington as a confident and skilled negotiator. Early in his administration, President Washington sent Pickering on special diplomatic missions to negotiate a peace agreement with the northeastern Indian tribes. Washington then appointed him, in succession, postmaster general, secretary of war, and secretary of state. 

The war between Great Britain and France continued to dominate American foreign policy. Pickering followed a pro-British agenda, and the 1795 Jay Treaty achieved many of his aims since it gave preferential treatment to Britain in matters of trade. But these terms angered the French, who regarded them as a violation of the 1778 treaties of alliance and commerce and began seizing U.S. merchant ships. President John Adams sent peace commissioners to renegotiate trade treaties, but they were not received by the French ministry. Instead, lower-level French diplomats demanded bribes before negotiations could begin in a scandal that became known as the XYZ Affair. Relations deteriorated further, and for the next two years U.S. and French ships attacked each other in an undeclared war, the so-called Quasi War. Pickering’s protests of Adams’s decision to send another commission to France led to his dismissal.

The Convention of 1800 ended the Quasi-War as well as the French alliance from 1778. In 1803 Pickering was elected senator from Massachusetts, and he later also served in the U.S. House of Representatives. A Federalist firebrand, he led the movement for New England secession during the War of 1812.