By the time neutral America officially joined WWI in April 1917 as an “Associate” of the Allies, Theodore Roosevelt had for two and a half years been carrying on a quixotic and unpopular struggle at home. This domestic crusade was fought against what he considered the craven neutrality of Woodrow Wilson, whose very presence in the White House TR blamed on himself. This talk examines these years in the multiple, intertwined, contexts of Roosevelt’s post-presidential political career, the preparedness movement, and the “Special Relationship” he fostered between America and Britain which helped define his perceptions of the war in Europe.