I have mixed views on Woodrow Wilson.
There is Wilson’s belligerent foreign policy record which embroiled us in World War I with Germany and nearly got us into the League of Nations and before that he sent American troops into Mexico to chase after Pancho Villa in addition to ordering the U.S. occupation of Haiti.
There is also Woodrow Wilson the Southern historian who wrote his five volume A History of the American People. This is the Wilson who resegregated the federal government and praised D.W. Griffith’s film The Birth of a Nation which was based on his old friend Thomas Dixon’s book The Clansman. I was reminded of this in reading Colin Woodard’s book Union which is a long diatribe about how Wilson brought the South back to power and revived the ethnonationalist conception of American national identity with his critique of Reconstruction and overall narrative of American history.
Theodore Roosevelt’s four volume The Winning of the West is a similar triumphalist account of American history. Roosevelt and Wilson shared many of the same flaws and virtues. TR was more eager to get into World War I than Wilson. I’ve written at length about how Wilson embroiling the country in World War I and Prohibition caused the rise of modernism in the Lost Generation which began the long arc of moral and cultural decline that has degenerated the country into what it is today.