Thought experiment, parts are a bit iffy.
George Washington (Independent) 1789*
John Adams (Federalist) 1789-1797
John Jay (Federalist) 1797-1801
Aaron Burr (Democratic-Republican) 1801-1809
Charles C. Pinnckney (Federalist) 1809-1811*
Rufus King (Federalist) 1811-1817
DeWitt Clinton...