I keep hearing that history will not to be kind to DJT.

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7. Wilson's an interesting case

For years he was generally rated top ten (and even top 5!) by historians and even now tends to rank fairly high (12-15 on surveys).

Wilson did a lot of things that would build on Theodore Roosevelt and presage FDR domestically (and Franklin was a big fan of Wilson, working in his Administration). He also was involved with the creation of the Federal Reserve, which which gave us the central bank rather than the various systems we had prior. Further Wilson helped birth the Federal Trade Commission to protest consumers. He also pushed through bills ending child labor and an 8 hour workday for railroad workers (which quickly became the norm in most other industries). Also despite initial ambivalence about the ratification of the 19th Amendment (for largely political reasons given the South's reluctance -- Wilson actually advocated for the state passage of giving women the right to vote, especially in New Jersey where he lived), near the end of WWI campaigned heavily for it, and was involved in the final ratification after it squeezed through Congress and went to the States.

On the other hand like you said there were his racism and the massive cracking down on dissent during WWI and its aftermath (I suppose given the German sabotage rings in the US prior to our entry it makes some sense, even if it presaged later presidents who didn't have a war to justify it).

Foreign affairs he seems like a revolutionary with the League of Nations and his general tendency toward pacifism, but he also got involved in Latin American affairs multiple times (sometimes unwillingly, but still).

I've sometimes say Wilson is kind of a perfect encapsulation of the US. There's a lot to admire and just as much not to.