What were the failures, contradictions, or mistakes of the Woodrow Wilson administration?

Answer 1

One of the biggest contradictions in the administration is that while Wilson was preaching democracy, he was enforcing segregation within his own administration.
Wilson effectively re-segregated the federal government, after decades of blacks and whites working together since the Civil War.

http://www.pbs.org/wgbh/amex/wilson/portrait/wp_african.html
http://www.dkosopedia.com/wiki/Woodrow_Wilson

The Espionage Act of 1917 and Sedition Act of 1918 are also black marks on Wilson's record.

http://en.wikipedia.org/wiki/Espionage_Act_of_1917
http://www.spartacus.schoolnet.co.uk/FWWespionage.htm
http://www.firstworldwar.com/source/espionageact1918.htm
http://en.wikipedia.org/wiki/Sedition_Act_of_1918