In 1782, Matthias Ogden won Washington’s approval for a scheme worthy of the Scarlet Pimpernel. He proposed to set fire to the outlying districts of New York City, then abduct Prince William Henry, the future King William IV, from his quarters there. The British blocked the plot when they destroyed Ogden’s boats.
Dayton’s military record was less gaudy. He began the war as paymaster in his father’s battalion, while whispers placed him amid the illegal smuggling between Elizabethtown and the British in New York.
In the New Republic
In peacetime, the Jersey Boys leapt at the great opportunities before them. They were distinguished veterans with Princeton degrees. They knew the right people. And they were determined to succeed.
Dayton started fastest, serving as the youngest delegate to the Constitutional Convention of 1787, when he was 26 years old. Elected as a Federalist to the House of Representatives, he became speaker from 1795 to 1799. In the late 1790s, when the United States teetered on the brink of war with France, Dayton was named brigadier general. A British diplomat recalled him as “a great rake” who confided that “he thought a reward should be offered for the discovery of a new pleasure.”
Drawing on his family’s wealth, Dayton led syndicates that speculated in lands in Ohio and beyond, deals that often carried a whiff of fraud and self-dealing. Matthias Ogden and Burr gave legal advice on his deals, and all of the Jersey Boys invested in them. Though one contemporary called Dayton “an unprincipled speculator, and crafty politician,” Dayton lent his name to the city founded on his Ohio lands.
Matthias Ogden, too, greeted peace with energy. In addition to his law practice and western investments, he won the New York-Philadelphia mail contract, owned a stagecoach line and built both a tannery and a mint. In 1791, however, yellow fever extinguished his bright promise.
Aaron Ogden started his law practice in New Jersey, while Burr built his in New York City. Burr entered politics as the only non-Federalist among the Jersey Boys. He became New York State’s attorney general, then United States senator in 1791. By the turn of the century, he was the foremost Northern figure in the Republican Party led by Thomas Jefferson.
Burr maintained friendships among Federalists and Republicans alike, which led both to mistrust him. Of the Republicans, a friend observed that “they respect Burr’s talents, but they dread his independence. They know, in short, he is not one of them.” Friendship was stronger than party for the Jersey Boys. When Burr emerged as the leading Republican candidate for vice president in 1796, the Federalist Dayton was suspected of scheming to get his boyhood friend elected.
Burr’s perceived independence led him to the threshold of the presidency four years later—and began his slide to political oblivion. At the time, each state chose electors who cast two votes for president. The candidate with the highest vote total became president so long as he had a majority; the runner-up became vice president.