Contra Jill Lepore in the New York Times, you don't need to watch Glenn Beck to dislike Woodrow Wilson. Nor do you need think there's any connection between one "professor-President" and the chap currently occupying the Oval Office. Radley Balko lays out the standard libertarian case against Wilson here and, frankly, it makes a pretty convincing argument that, even by the lofty standards of the field, Wilson was one of the most unpleasant men ever to hold the Presidency. And that's before you consider Jim Crow and his penchant for launching extra-constitutional wars...
Well, as Radley says, historians tend to approve of Presidents who "do stuff" which in turn means they approve of Presidents who exceed their constitutional authority. That's a feature or a virtue not a bug or an indictment.“
Lepore is correct that some of these libertarian objections are actually points of similarity between Wilson and modern conservatives. But I think a more interesting question than Why does the right hate Wilson? is, given all of this, along with his belief in white racial superiority and opposition to women’s suffrage, why do presidential historians seem to like him so much?
The two great themes or, if you prefer, narratives of American history are slavery (and its legacy) and the United States' rise to superpower status. The nation's original disgrace is such that any number of presidents are stained by it and this, in some sense, protects them from being singled out. America's rise to international promise - fulfilling its manifest destiny - is a different matter. Not every President contributed to this; some even thought it regrettable. But it's Big History, the sweeping kind that begins with the push west across the continent and ends with an Empire of America's own.
Wilson, with his punitive raids on central America ("I will teach them to elect good men"!) fits enthusiastically into this narrative. Furthermore, viewed from a Baby Boomer perspective that recognises few limits on American power and influence, the supposed interwar period of "isolationism" is a backwards-looking, regrettable interlude responsible, at least in part, for failing to thwart the horrors that would be unleashed in the 1940s. If only the United States had led!
So while Wilson's personal views on women's suffrage, civil liberties and Jim Crow might be best discreetly overlooked, his vision counts for more - especially amongst the kinds of historian who tend to be polled in these historical ranking exercises. After all, many of them are Presidential historians who, understandably, are biased in favour of activist Presidents. And since the President has traditionally enjoyed greater discretion in foreign affairs it's not surprising that - justly or not - interventionist Presidents such as Wilson and TR score better than more modest types such as Cleveland or Coolidge.
It is precisely because Wilson was the first sitting President to visit Europe and proclaim the United States' arrival as a global power (one that would refashion the globe to boot) that he's still ranked so highly. (Even if, I think, his reputation has crested and is now declining.) While his record on segregation is nothing special - that is, awful - his Presidency marks an important stage in that other American narrative and so he "scores" highly because of that.