AHC: President Isaac Roosevelt

Perhaps John Adams dies early and Isaac Roosevelt becomes a bit more of a political leader in New York and in the state's Constitutional Convention (as well as helping get it ratified, being crucial in ratification might do the trick). He's selected as Washington's Vice President.

From there you could go two ways. Washington could either decide to retire in 1792 and Roosevelt is elected President, serving for one term until he dies in 1796 (by which time he's retired from the office anyway, following the precedent of Washington).

Alternatively, you could hope a different later life for Roosevelt butterflies away his 1796 death by being in better health or whatever have you. He'll be elected President in 1796.

"Everybody likes Ike for President in 1796!"
 
It's a crowded field of far better known, better connected, extremely able, and already regional or national figures ahead, several dozen men many of whom do become President, Vice President, Cabinet Officers, Constitutional Convention Delegates, War Heroes, Governors, etc. so Isaac would need a significant role in the Continental Congress, the Battle of Saratoga, New York's business world, and probably first elected/American governor of New York State to be in the running for President after Washington.

Heck his descendants are unlikely Presidents too, but both had served as Governors of New York, Undersecretary of the Navy, and other jobs they handled in a high profile way while Theodore had numerous books and articles to his fame as well as the much hyped Rough Riders' brief campaign.

Isaac's up against Adams, Jefferson, Madison, Monroe, Hamilton, Burr, Morris, Pinckney, Knox, Greene, Hancock, etc. rather than the weak candidates his descendants would run against.
 
Top