I never understood why Woodrow Wilson is lauded in the history books, and comes out in historians' presidential rankings quite well. His administration (and he personally) had a pattern of suppressing free speech with prison time. That, and he created the Federal Reserve (which then went on to create the Great Depression, as it slowly learned to use its powers). Whether or not you think a central bank is a good thing, it certainly belies his ideology that the government knows best.
The Federal Reserve absolutely did not cause the Great Depression. Economic crashes occurred at least once a decade since beginning of American history, and as the economy grew more more interconnected and less self sufficient, economic crashes tended to be worse than the last, culminating with the Great Depression. Economists overwhelmingly agree that the Fed's biggest blunder during the Great Depression was not going far enough. It was only with what I'm sure you would call "money printing" enabled by the Fed to finance WWII, that the economy truly recovered.
Small-scale economic downturns did happen once a decade, because that's natural in a healthy economy. Federal Reserve tried to prevent a downturn in 1929, but their misguided monetary policies made it two orders of magnitude worse instead. Milton Friedman once wrote a great analysis on this: https://fee.org/articles/the-great-depression-according-to-m...
Most people can't name any specific recession prior to the creation of the Federal Reserve, but everyone has heard of the Great Depression. A sibling commenter posted some good analyses, but the gist of it is that they tried tightening the money supply at the worst possible time (something the modern Fed avoids at all cost, at the expense of increasing wealth inequality by artificially inflating the value of assets whenever they start to dip).
>...While Wilson's tenure is often noted for progressive achievement, his time in office was one of unprecedented regression in regard to racial equality.[1] He removed most federal officeholders who were African Americans, his administration imposed segregation policies, and instituted a policy requiring a photo for federal job applicants.
Wilson was “one of their own”—a professor at Princeton. He was also the founder of the ideology of governance by credentialed experts, which is unsurprisingly popular among highly credentialed people, like historians.
Also, Wilson got the United States into World War One, which helped to put the US on its trajectory to eventually being involved in World War Two and subsequently becoming the world's top geopolitical power. So I suppose that people who think that it was good for the United States to be involved in World War Two and/or people who think that it is good for the United States to be the world's top geopolitical power - which is a pretty large number of people, at least in the West - have those reasons to like Wilson.
I’ve seen a lot of negative backlash against Wilson’s legacy in recent years, to the point of verging on overreaction. He is in an awkward position since he was too progressive for conservative tastes and too racist for liberal tastes. The main positive thing people used to say about Wilson’s legacy was his championing of liberal internationalism, combined with lots of bemoaning the fact that the US didn’t ratify Versailles or join the League of Nations due to isolationist obstruction in the Senate.