[citation needed] Wilentz's historical scholarship has focused on the importance of class and race in the early national period, especially in New York City.

Wilentz returned to the pro-Jackson themes of Arthur Schlesinger Jr., who in 1946 had hailed the pro-labor policies of Northern, urban Jacksonians.

He received a Grammy nomination[10] and a 2005 ASCAP Deems Taylor Award for the liner notes Wilentz contributed to the album The Bootleg Series Vol.

His testimony cheered Democratic partisans but was criticized by The New York Times, which lamented his "gratuitously patronizing presentation" in an editorial.

In response, the National Review attacked Wilentz's analysis as "blinkered" and called him "the modern Arthur Schlesinger Jr."[16] Wilentz followed up during the 2008 general election with another article in Rolling Stone describing how the failures of the Bush administration had caused a "political meltdown" of the Republican Party, with potentially enormous long-term effects.

"[20] During the 2008 Democratic National Convention, Wilentz charged in Newsweek that "liberal intellectuals have largely abdicated their responsibility to provide unblinking and rigorous analysis" of Obama.

[22] In January 2014, Wilentz took issue with those involved in the 2013 NSA leaks, in particular Edward Snowden, Glenn Greenwald, and Julian Assange.

The leakers and their supporters would never hand the state modern surveillance powers, even if they came wrapped in all sorts of rules and regulations that would constrain their abuse.

He further wrote that Trump and Attorney General William Barr had created the greatest "existential crisis for American democracy" since the American Civil War through their alleged politicization of the U.S. Department of Justice and attempted delegitimization of the 2020 presidential election, comparing Trump's ideology to the Confederacy and calling it "a bacillus of racism and authoritarianism."

He also claimed Barr was advancing "an Americanized version of something more akin to Generalissimo Francisco Franco's Spain" and "a theocracy, overseen by a president who more closely resembles an elected monarch.

"[24] After the 2021 United States Capitol attack Wilentz predicted that if Trump and the Republican Party returned to power in the 2022 and 2024 elections, they would legally establish "a more or less ironclad system of undemocratic minority rule" to permanently block liberal policies and end majority democracy, calling them "right-wing Bolsheviks."