Rick Wilson

After the second election of Trump in 2024, Wilson became a senior adviser to the left-of-center Two Plus Two Coalition opposition research project. ⁴

Overview

Rick Wilson has worked as a campaign strategist for Republican campaigns and organizations including former President George H.W. Bush, former New York City Mayor Rudolph Giuliani (R), former U.S. Sen. Saxby Chambliss (R-GA), the Republican National Committee, and the Republican Governors Association. ¹

Wilson is based in Florida, where he and his company Intrepid Media worked on statewide campaigns for Republican politicians including former U.S. Representative Katherine Harris (R-FL) and former state Chief Financial Officer Jeff Atwater (R). ^{1 5}

He is a board member of the left-of-center voter mobilization group VoteRiders. ⁶

Opposition to Donald Trump

Rick Wilson rose to national prominence for his opposition to Donald Trump’s presidential candidacy and first administration. He is frequently described as one of the founders of the “Never Trump” movement of Republican and formerly Republican critics of President Trump. ^{7 8} He was also an adviser to the effort to launch an independent right-of-center 2016 presidential campaign that ultimately ran Evan McMullin (I-UT). ⁹

Wilson’s book, Everything Trump Touches Dies: A Republican Strategist Gets Real About the Worst President Ever, reached #1 on the New York Times Nonfiction Bestseller List in August 2018. ¹⁰

The day after Donald Trump’s second election in 2024, Wilson wrote to his Substack newsletter subscribers, “I failed you. I did everything I could think to do.” ¹¹

Lincoln Project

Rick Wilson co-founded the anti-Trump Lincoln Project super PAC in late 2019 with other Republican and formerly Republican critics of Donald Trump.  ¹²

The Lincoln Project was criticized for spending less than a third of the money it raised during the 2020 election cycle directly on advertising buys, and an investigation by the Associated Press found what the AP characterized as “exorbitant consulting fees collected by members of the group,” including Wilson. ¹³ In 2021, the New York Times reported that Wilson was one of four Lincoln Project co-founders to split roughly $27 million out of a $90 million “geyser of cash” raised from donors. ³

According to reporting by the New York Post and Washington Free Beacon, Wilson faced numerous personal financial challenges before the creation of the Lincoln Project, including a $389,420 federal tax lien against his home and $25,729 in unpaid American Express credit card bills. ^{14 15}

In 2023, Politico reported that the Lincoln Project had hired Wilson’s son, Andrew Wilson, as an independent contractor to do “corporate campaign management.” ¹⁶

Two Plus Two Coalition

Following the second election of Donald Trump in 2024, Wilson became senior advisor to the Two Plus Two Coalition, a left-of-center opposition research group that the New York Times characterized as having “a military-grade intelligence-gathering operation that went far beyond the document vetting typical of a political campaign.” ⁴

It began its fundraising by making what the Times reported as requests for minimum million-dollar donations with “a pitch that it would unearth unflattering revelations about the Murdoch family and Elon Musk — both pro-Trump media magnates.” ⁴