Evaluate Wilson's Fourteen Points against the actual Treaty of Versailles, and explain why the U.S. Senate rejected the League of Nations.
In January 1918, before the war even ended, Wilson outlined Fourteen Points for a just and lasting peace: no secret treaties, freedom of the seas, reduced armaments, self-determination for European nationalities, and, as his fourteenth and favorite point, a League of Nations to prevent future wars through collective security. Wilson traveled to the Paris Peace Conference in 1919 to argue for this vision personally -- an unprecedented move for a sitting American president. But he had to negotiate with French and British leaders who had lost millions of citizens and wanted Germany punished, not merely restrained. The resulting Treaty of Versailles (signed June 28, 1919) forced Germany to accept full blame for the war, pay enormous reparations, and lose territory and its overseas colonies -- far harsher terms than Wilson's original vision, though the League of Nations he wanted was included.
Back home, the treaty faced a Senate deeply skeptical of the League of Nations, particularly its Article X, which seemed to commit the U.S. to defend other member nations militarily -- a commitment critics like Senator Henry Cabot Lodge argued would drag America into future European wars without full congressional control. Wilson refused proposed compromises and toured the country making his case directly to voters, collapsing from a stroke partway through in October 1919 that left him seriously disabled for the rest of his term. The Senate rejected the treaty in votes in November 1919 and March 1920; the United States never joined the League of Nations, signing a separate, simpler peace with Germany in 1921. This is a genuinely instructive case for evaluating a leader's legacy even-handedly: Wilson's vision for preventing future wars through international cooperation was farsighted, and the same uncompromising personality that built that vision may also have cost him the political flexibility to see it through in his own country.
Mastery looks like: They can name at least two Fourteen Points, explain how the actual treaty differed, and state why the Senate rejected the League of Nations.
Common stumbles: Assuming Wilson simply "got his way" at Versailles because the League of Nations was included, without recognizing how much of his original vision was compromised -- or that he then lost the fight at home entirely.