Woody Wilson was one of the first high level pols to support the left wing, Communist, agenda. He pretty much initiated the Marxist plan to overthrow our Constitution that was kicked to the curb last November 8. One hundred years of scheming and planning shot to Hell by an avaricious harridan with only personal power on her mind.
Woodrow Wilson and his “Progressives” were no more than Marxists in disguise. This was the government that gave us the 16th, 17th and 18th amendments, all of which are trash.
The 18th was repealed but we still need to repeal the 16th and 17th to return our nation to a Republic.
The real difference between left and right here is that our side wants to improve it slowly and carefully through the prescribed means, understanding that there are unintended consequences and perverse interests that are likely to make things worse if one cheats and rushes the process through legal fictions and what not.
That's more or less where Wilson ended up, but that's not where he started out.
19th century Europe identified the abstract theories of natural rights (Newtonian, Whiggish) with the French Revolution and its violence. They (Burke, Hegel) wanted to get away from a mechanical theory of society and move to an "organic" developmental or evolutionary model.
The idea was for society to evolve naturally according to its own inner nature and not be forced by rationalistic or mechanistic efforts to remake society. Wilson's teachers thought that way and the young conservative Wilson picked up on their thinking. Society was supposed to evolve naturally and not according to some rationalistic blueprint. Darwin was another influence pointing in the same direction.
At some point, though, Darwinian and Hegelian thinkers like Wilson and Dewey began to think that intellectuals could influence and shape the direction of evolution, and what was a conservative way of thinking became progressive and activist. Wilson's present day critics pit him against the natural rights thinking of the American Revolution and find him wrong or deficient, but the debate when he was young had more to do with the French Revolution.