Thomas Jefferson and Woodrow Wilson are influential American political figures who are famous for the succession and development of Jeffersonianism. Through Jeffersonian liberalism and textual analysis of the 14 Points by Woodrow Wilson, the paper finds that 14 Points expand American politics from domestic affairs to international political (covenants and open diplomacy), economic (freedom to navigate of all time), military (reduction of armaments), moral and cultural (national self-determinism all over the globe) issues, through the League of Nations as a way to isolate itself from European order and alliances. Besides, the colonies are excluded from independence despite some equal treatment. Expansionism, isolationism and racism are what Wilson inherited from Thomas Jefferson.