Segregation is not humiliating. It's a benefit!

Historymatters has a portion of an exchange online between President Woodrow Wilson and Monroe Trotter.

President Woodrow Wilson: The white people of the country, as well as I, wish to see the colored people progress, and admire the progress they have already made, and want to see them continue along independent lines. There is, however, a great prejudice against colored people.... It will take one hundred years to eradicate this prejudice, and we must deal with it as practical men. Segregation is not humiliating, but a benefit, and ought to be so regarded by you gentlemen. If your organization goes out and tells the colored people of the country that it is a humiliation, they will so regard it, but if you do not tell them so, and regard it rather as a benefit, they will regard it the same. The only harm that will come will be if you cause them to think it is a humiliation.

It would be easy just to wipe this off the table as the rantings of a hardcore racist and move on, but that would be a mistake.(Wilson was a racist, but I believe this is his progressive elitism speaking, not his racism) Here's what I mean:

The competent leader of men cares little for the interior niceties of other people’s characters: he cares much-everything for the external uses to which they may be put. His will seeks the lines of least resistance; but the whole question with him is a question of the application of force. There are men to be moved: how shall he move them? He supplies the power; others supply only the materials upon which that power operates. The power will fail if it be misapplied; it will be misapplied if it be not suitable both in kind and method to the nature of the materials upon which it is spent; but that nature is, after all, only its means. It is the power which dictates, dominates: the materials yield. Men are as clay in the hands of the consummate leader.

That comes from Wilson's "Leaders of Men".

According to the William Monroe Trotter House:

In 1909 Trotter and Du Bois founded the National Association for the Advancement of Colored People (NAACP), but Trotter objected to the new organization's white financing and leadership, preferring his own alternative "National Equal Rights League."

Wilson clearly viewed the "National Equal Rights League" as a 'leader of men'. And what he's telling Trotter is that his group should be molding the clay. Considering all that happened with the CPI, the Five Minute Men, and all of Wilson's other propaganda efforts during his presidency, Wilson didn't think that molding the clay was just limited to blacks. That's why I don't see this as primarily an example of racism.