Elbridge Gerry

Signer of the both the Articles of Confederation and the Declaration of Independence, Elbridge Gerry was a major political figure of colonial Massachusetts who died in office as vice president under James Madison. A graduate of Harvard College (1762), Gerry was a shipping merchant who used his procurement skills to aid the colonists in their revolt against England's King George III. He served in the Continental Congress (1776-81) and was elected to represent Massachusetts in the House of Representatives in the new government, serving from 1789 to 1793. Gerry worked under President John Adams as a negotiator with France (1797-98), then returned to Massachusetts, where he ran unsuccessfully for governor four times (1800-1803) before finally getting elected to consecutive terms (1810 and 1811). His deepest groove in history comes from one of his last acts as the Massachusetts governor: prior to the 1812 elections he signed a bill that restructured voting districts to give his party, the Democratic-Republicans, a majority in the legislative body. Since then, such activity has been known as "gerrymanding." Like his vice presidential predecessor George Clinton, Gerry was chosen as a vice presidential candidate in 1812 to bring the northern votes for Madison, a Virginian who'd been picked to follow Thomas Jefferson into the presidency. And, just like Clinton, Gerry died while serving as vice president.

Extra credit: Ironically, Gerry's wife, Ann Thompson Gerry, didn't join him in Washington, D.C. for his vice presidential term because of her ill health, yet she outlived him by 35 years.