Pure linkbait, that title. I mean, the guy is so hot right now, his name guarantees an avalanche of visitors.
But what do I say when they get here? That I don't get what's up with Woodrow Wilson? I think liberals try to defend him because he was...well, an intellectual, an Ivy Leaguer with big schemes and an unexpected skill for political infighting. But his schemes were crazy, he resegregated Federal employment, and he dragged us into a war that there were good reasons for avoiding. Leftists have no reason to love him.
On the other hand, he's not responsible for creating the national state we now have. That was a cooperative effort of many people, on both the right and the left. Rightists just hate his annoying teacher's pet personality.
There's an interesting twist near the end of Robert Heinlein's novel Time Enough For Love, where the hero, Lazarus Long, who has traveled back to the early Twentieth Century to have sex with his mother (it's from that period of Heinlein's writing, so be warned), gets caught by America's entry into WWI because he's not really paying attention. He has every reason to keep out of it, knowing it's going to be a big mistake for everyone, but the women in his life want him to go, so he does. This is portrayed as somehow heroic, rather than cowardly, at least as I remember it. It certainly isn't one of those books I insisted on keeping in my library for years, so regard this reference as less than dependable. But how can you condemn Wilson's overambitious internationalism without also condemning military interventions in pursuit of national power? (Addendum: as I should have mentioned, "Lazarus Long" is a nom de methuselah: his birth name was...Woodrow Wilson Smith! Wouldn't a revelation of Heinlein's secret devotion to Woodrow Wilson really cause some trouble?)
Even Gore Vidal, who really should know better, offers a charming portrayal of Wilson in his Hollywood. Given Vidal's political position, Wilson's manipulations and gigantic schemes for reformulating the world should have appalled and disgusted him, but the fact that conservatives have been bashing Wilson since the time of their beloved Teddy Roosevelt (another overweening statist, as it happens) tempted Vidal into defending him--or at least his personal character.
The wise thing is to prefer Presidents who are pragmatists with clear and limited goals to those who are extravant theorists, no matter what their political coloration. To oversimplify, Wilson called Eugene V. Debs a traitor for his words and threw him in jail. Warren G. Harding let him out. Who looks more respectable? And what should that say about their postumous reputations?