Financial Problems Plagued Rick Wilson as He Became Never Trump Leader
Matthew Boyle 17 Jun 2020
Never Trump leader Rick Wilson’s hypocrisy is not limited to now attacking those who support the Confederate flag after previously supporting it himself.
As Wilson’s personal financial situation turned dire in the lead-up to the 2016 presidential election, the political operative with a long history of backing bomb-throwing right-wingers began to reinvent himself pursuing what financial records indicate is a more lucrative book-deal-filled career in bashing President Donald Trump and his supporters.
Records demonstrate that as Trump was taking off as a political force, Wilson’s personal financial situation turned dour. The bank was moving in on his house, credit card companies were suing him over debt accrued, and the IRS filed various liens against him for almost $400,000 for back taxes in February 2014. As that happened, Wilson’s political style changed to become anti-Trump instead of continuing with his decades-long history of inflammatory right-wing politics.
Wilson’s The Lincoln Project, a group of Never Trump political consultants running targeted ads attacking Trump this year, has been touting an ad bashing the Confederate flag as a symbol of “treason” against the United States.
“The men who followed this flag 150 years ago knew what it meant,” a narrator says in the ad released earlier this month as a Confederate flag waves in the background. “Treason against their country. The death of the United States. America defeated the men who followed that flag. Those with honor surrendered and cast it aside forever.”
But then some conservatives uncovered social media posts from Wilson and his wife featuring a cooler with a Confederate flag on it as well as the text in one image: “The South Will Rise Again.” Wilson has been feverishly deleting the images from Twitter, and when his wife, Molly—legal name Mary—was confronted by conservative Caleb Hull, she would not deny owning the cooler or disavow the Confederate flag on it. She simply replied “Fuck off” to Hull, per screenshots he posted of his confronting her about it.
Wilson is also getting lots of national attention this week after attempting to shame Dominos Pizza for thanking now White House press secretary Kayleigh McEnany for praising their pizza back in 2012. “You just killed your brand,” he tweeted at Dominos with a screenshot of the pizza chain’s 2012 reply to McEnany’s tweet from eight years ago. At the time, McEnany was not in a government political position but was a civilian. Later, Dominos joked in response that it’s “unfortunate” to think the company would be held responsible for something from 2012 in 2020.
But these latest mishaps by Wilson come after years of him leading a small and shrinking band of GOP political consultants who dub themselves Never Trumpers furious with Trump’s rise ahead of their more-preferred 2016 GOP candidates during that year’s primary.
Prior to turning against the party over Trump, Wilson, whose legal name is Frederick George Wilson Jr., had long been a fixture in Republican circles. His career as a media consultant, strategist, and ad-maker is intertwined with several major political events of the last 30 years and his flair for the dramatic—and viciously negative—style of ad could make even Trump’s aggressive nature look timid.
Officially, Wilson, a Florida native, got his start on George H.W. Bush’s successful 1988 presidential campaign. During that race, although only the Florida field director, Wilson was supposedly mentored by Bush’s campaign manager, Lee Atwater—the mastermind behind the infamous Willie Horton television ad.
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