To the campaign to make "progressive" a slur, Wilson is useful. Much as many people admire aspects of his presidency, he has no natural constituency any more, right or left. He was opposed to female suffrage. He supported Jim Crow. He wrote about Anglo-Saxon racial supremacy. He makes a good bad guy. He was also an intellectual, the first U.S. president to hold a Ph.D., and not just any intellectual: he had a law degree, but, before he became president, he was an American historian, with a special interest in constitutional history.
This professor-president has convenient similarities to our current chief executive — a scholar of constitutional law, professorial, intellectual, even, in some people's eyes, effete (as, for instance, T.R. and F.D.R. were not). Also, given that Tea Party populism, at least as represented by remarks made by Glenn Beck and Sarah Palin over the last two years, is dedicated to the proposition that American history — the very study of the nation's past—has been stolen by elitist, leftist intellectuals, discrediting Wilson, broadly, as an intellectual and, specifically, as an American historian, is tactical.
Finally, of course, Wilson was indeed a progressive; he pursued progressive policies, and nominated progressives like Louis Brandeis to the Supreme Court. Nevertheless, targeting Wilson is, to some degree not only arbitrary but also counter-intuitive; much that he wrote aligns very well with today's far right ("America was born a Christian nation," Wilson once said).
I can't speak for Glenn Beck, the Tea Party, or conservatives, but I'm not the least bit bothered by the fact that Wilson was an intellectual (it's the content of his academic writing that I find objectionable), and I don't really think he has all that much in common with Obama. But while the animus toward Wilson from the right is relatively new, or at least more pronounced than it's been in the past, Wilson has always drawn the ire of libertarians. Among the many reasons why:
- He dishonestly led us into a pointless, costly, destructive war, and assumed control over huge sectors of the economy to wage it. He seized railroads, food and energy production, and implemented price controls.
- He suppressed dissent and imprisoned war critics. Said Wilson, "Conformity will be the only virtue. And every man who refuses to conform will have to pay the penalty." He signed the Espionage and Sedition Acts, the latter of which made it a criminal offense to "oppose the cause of the United States." He retaliated against critical newspapers, and directed the U.S. Postal Service to stop delivering mail determined to be critical of the war effort.
- Wilson not only continued existing racial segregation of federal government workers, he extended it.
- He instituted the first military draft since the Civil War.
- He signed the first federal drug prohibition.
- He reinstituted the federal income tax.
A few more, from Gene Healy's book, The Cult of the Presidency:
- Wilson believed in an activist, imperialist presidency. In his 1909 book Constitutional Government, he made the case against checks and balances and the separation of powers. The government, Wilson argued, is a living organism, and "no living thing can have its organs offset against each other as checks, and live."
- He ordered unconstitutional, unilateral military interventions into Haiti, the Dominican Republic, and Mexico. (He also oversaw military interventions in Panama and Cuba, and instituted American-favored dictators throughout Latin America.)
- Wilson believed God ordained him to be president, and acted accordingly, boasting to one friend in 1913 that "I have been smashing precedents almost daily every since I got here." Every president since Jefferson had given the State of the Union in writing. Wilson reinstituted what Jefferson derided as the "speech from the Throne," and ordered Congress assembled to hear him speak, giving rise to the embarrassing spectacle the SOTU has become today.
- He oversaw a massive domestic spying program, and encouraged American citizens to report one another for subversion.
Lepore is correct that some of these libertarian objections are actually points of similarity between Wilson and modern conservatives. But I think a more interesting question than Why does the right hate Wilson? is, given all of this, along with his belief in white racial superiority and opposition to women's suffrage, why do presidential historians seem to like him so much? Similarly, why do historians seem to be most smitten with the presidents who most exceed their constitutional authority?