Anti-Trump activism
On November 9, 2018, Conway and Neal Katyal wrote an op-ed in The New York Times challenging the constitutionality of Trump's appointment of Matthew Whitaker as acting attorney general following the termination of Jeff Sessions. Trump relied on the Federal Vacancies Reform Act of 1998 (FVRA), which allows the president to make interim appointments, to appoint Whitaker. Conway and Katyal argued that it was a mistake to try to use the FVRA to override the explicit wording of the Constitution, which requires Senate approval of all appointees who answer directly to the president.
In November 2018, Conway organized a group called Checks and Balances. The group was composed of more than a dozen members of the conservative-libertarian Federalist Society, which had been instrumental in selecting candidates for the Trump administration to appoint to federal courts. The New York Times reported that the group was "urging their fellow conservatives to speak up about what they say are the Trump administration's betrayals of bedrock legal norms".
Conway is a founding member and advisor of the Lincoln Project, a conservative Super PAC formed in December 2019 and dedicated to "Defeat President Trump and Trumpism at the ballot box". Its detailed aim is "persuading enough disaffected conservatives, Republicans and Republican-leaning independents in swing states and districts to help ensure a victory in the Electoral College, and congressional majorities that don't enable or abet Mr. Trump's violations of the Constitution". The group released its first video on January 9, 2020; called "The MAGA Church"; it warns evangelicals to beware of false prophets. On August 23, 2020, he announced that he would be taking a leave from the Lincoln Project in order to devote more time to his family. Kellyanne Conway, his wife, announced her departure from the White House the same day as well. In 2021, Conway said that the Lincoln Project should shut down after it was revealed that members of its leadership ignored warnings that another founder was harassing young men, including interns.
Following the first impeachment of Donald Trump, Conway opined in The Washington Post that if the relevant witnesses are not allowed to testify during the Senate Trump impeachment trial, Trump's defenders will be negatively affected by "the very evidence they sought to suppress". Upon Senator Mitch McConnell's refusal to subpoena John Bolton in a Senate impeachment trial, Conway and Neal K. Katyal opined in The New York Times, "There is only one possible explanation for this behavior: [McConnell] is afraid of the truth. Otherwise, what argument can there be for refusing to hear from a central witness like Mr. Bolton, who other witnesses have indicated was exceptionally concerned about the suspension of military aid to Ukraine?"
In April 2024, Conway donated the maximum legal amount of $929,600 to the Biden Victory Fund. When questioned about why he made the donation, Conway told CNN that he believed the election crucial for upholding democracy and the rule of law.
In May 2024, Conway funded a billboard directly on the path from Mar-a-Lago to Doral, where Trump plays golf. The advertisement said "Vote for Joe, not the psycho".
Since 2018, Conway's stated political positions have often been contrary to those taken by his wife on behalf of the Trump administration. His published legal interpretations of Trump's actions differ from his wife's positions, and on Twitter he has been critical of Trump on a personal level. In March 2019, Trump responded to Conway's attacks by calling him a "stone cold LOSER & husband from hell" on Twitter. Trump has called Conway "Deranged loser", "Whack job", "Moon face". Kellyanne defended Trump's comments in an interview, saying that Trump was "a counterpuncher" and was free to respond when he is attacked. Conway has said of Trump: “The lowest form of life on Earth.”
