Was Woodrow Wilson really a Liberal?

My question, which this OP refers to, uses the term "classical liberalism" and uses Hayek as a reference point to make sure that I'm not misunderstood. Classical liberalism doesn't mean at all what it sounds like to someone who is thinking in terms of the usage of "liberal" in today's United States. In its economic dimension, it means almost the opposite of that. Classical liberalism refers basically to laissez faire capitalism, i.e., the opposite of US "liberalism," if you're thinking in terms of a unidimensional political spectrum based on economic policy.

Classical liberalism also has more than an economic dimension. It involves civil liberties and the rule of law, which is what distinguishes it from things like statism, fascism, and Chinese-style state capitalism.

In economic terms, the political norms of the US in that era were indeed laissez faire capitalism with a small and weak federal government. Wilson fit solidly within those norms.

But in terms of civil liberties and the rule of law, there is no possible way to shoehorn Wilson into classical liberalism. His presidency represented an abrupt regression in those areas. The Ku Klux Klan, which had been destroyed by the Republicans during early reconstruction, was rebuilt in 1915 as a terrorist organization, and as noted by the OP, Wilson heartily approved of the new Klan and publicly gushed over its propaganda. The federal government was resegregated under Wilson. The East St. Louis Massacre happened on Wilson's watch, as dramatized by the cartoon below, with the caption "Mr. President, why not make America safe for democracy?" The first Red Scare and the Palmer raids were new phenomena in which civil liberties such as freedom of the press was attacked in an unprecedented way.

So no, Wilson was not a liberal even in the sense of being a classical liberal. He represented a full-blown attack on the ideals of classical liberalism. Even by the standards of the time, his administration was a marked regression in civil liberties and the rule of law.

As the comments go into, it depends on your definition of "Liberal".

If you go with the common usage in modern US political parlance, which essentially means "embodies everything the Republican Party is against", then no he wasn't. Not even close.

If you go with the sense of Classical Liberalism, then that was indeed fundamentally his outlook.

Classical liberalism is a political ideology and a branch of liberalism which advocates civil liberties under the rule of law with an emphasis on economic freedom.

Nobody perfectly embodies an idealized concept of course, but this was fundamentally his outlook wrt governments in the large, embodied in his 14 points:

The speech made by Wilson took many domestic progressive ideas and translated them into foreign policy (free trade, open agreements, democracy and self-determination).

Note that first half of the description there is economic. Classical liberals were strongly against interference in the free market, by organized cartels, unions, or governments.

In the US in the 1950's a lot of the remaining adherents to this political philosophy quit calling themselves "Liberals" and started self-identifiying as "Libertarians".

H. L. Mencken and Albert Jay Nock were the first prominent figures in the United States to privately call themselves libertarians. They believed Franklin D. Roosevelt had co-opted the word liberal for his New Deal policies which they opposed and used libertarian to signify their allegiance to individualism. ... However, the term libertarianism was first publicly used in the United States as a synonym for classic liberalism in May 1955 by writer Dean Russell...

The fit may not be perfect (for one thing, the issues today are completely different), but if you are more familiar with the modern US usage of political terms, it may be easier for you to think of Wilson as a Libertarian¹.

The traditional foil of the (Classical) Liberal outlook in that era was Reactionary² which prior to WWI basically meant upholding a more traditional paternalistic political system, where power flows only from the top down, and few if any citizens have any real say in their government. This is the philosophy he was fighting in Europe, and which the war more-or-less dismantled. Of the 6 "major powers" in Europe involved in the start of that war in 1914, at the start of the war there were 4 authoritarian "Empire"s complete with inherent social classes, and at the end of the war there were 0 of them.

The question's hits against Wilson's "Liberalism" are generally not talking about Classical Liberalism at all. Instead, this is covered under a very different political philosophy that Mencken and Nock believed FDR appropriated the term to cover, and which "classical" liberals did not approve of. This new system is often today called Social Liberalism.

Social liberalism (also known as modern liberalism in the United States and left liberalism in Germany) is a political ideology and a variety of liberalism that endorses a regulated free market economy and the expansion of civil and political rights. A social liberal government is expected to address economic and social issues such as poverty, health care and education in a liberal state.

Its certainly true that Wilson was not one of those.

^{1 - Understand that "Libertarian" only has this meaning today in American English. In most of the rest of the world, Libertarians are considered far left wing, and can encompass both Marxists and Anarchists. The meaning of political words is heavily-reliant on context.}

^{2 - Ironically this term was also appropriated in the US as a mere pejorative label to tar the other political party with}