Matt Yglesias is surprised to learn that Woodrow Wilson has a good reputation. Alas, it's true. Many scholars consider him a great or near-great president. For what it's worth, I know that when I teach the presidency -- and bashing Wilson is a fun part of that -- I run into a lot of students who are shocked to learn that not everyone loves Woodrow Wilson, which I take to be evidence that high school history books and high school history teachers tend to leave their students with a positive impression of him.
As far as why Wilson is overrated, I don't think it's actually much of a mystery. Midcentury historians and political scientists were big fans of Franklin Roosevelt (with good reason), and tended to see the world through FDR-tinged glasses. Wilson's strengths and weaknesses are almost perfectly designed for that. If the big question is isolationism vs. internationalism, Wilson is on the correct side. If it's government intervention in the economy vs. laissez faire, Wilson is basically on the correct side of that, too. FDR fans also tended to be supporters of the president against Congress, and from that vantage point Wilson's early legislative victories are a good example of presidential domination, while his League defeat looks like a case of Congressional misbehavior against presidential good intentions, a story that midcentury historians and political scientists were eager to tell.
Wilson's weaknesses were easy to overlook or miss entirely. On race -- and Matt is absolutely right about Wilson's disgraceful record -- it's no surprise that the same academics who idolized Adlai Stevenson also praised Wilson. Northern Democrats of the 1930s, 1940s, and 1950s, while probably notionally in favor of integration, were in fact supporting a party, and many candidates, that were operationally willing to let the South do whatever it wanted to do (and of course were also all too willing to see race as just a Southern problem). Meanwhile, the focus on Internationalism Good, Isolationism Bad obscured other important questions, including Wilson's actual performance with regard to foreign affairs. It's probably not a big surprise, either, that the people who supported FDR would overlook Wilson's miserable record on civil liberties. And Wilson's sometimes shockingly poor management of the presidency, most notably his bungling at Versailles and in the League battle, were ignored or blamed on others.
Presidential reputations tend to be sticky, I guess; one would think that Wilson's reputation would fade as the midcentury conditions that helped his reputation recede farther into the past. At least I hope it will.