Financial Problems Plagued Rick Wilson as He Became Never Trump Leader

NEW YORK, NEW YORK - NOVEMBER 07: Rick Wilson speaks on stage at the "2020 Vision: Political Roundtable" panel at the on November 07, 2019 in New York City. (Photo by Brad Barket/Getty Images for Fast Company)
Brad Barket/Getty Images for Fast Company

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.

Wilson’s profile only grew after that campaign. In 1993, he signed up with Adam Goodman, another Florida political consultant, to advise Rudy Giuliani, who was then seeking the office of mayor of New York City, on media strategy. Wilson and Goodman reprised their roles when the mayor was seeking reelection in 1997. This time, though, they entered New York political folklore by crafting an ad that for many epitomized for many voters the progress made under Giuliani.

The ad, known simply as “sex shops,” hit Giuliani’s Democrat challenger for opposing his administration’s proposal to shutter pornography retailers in commercial districts and residential neighborhoods, most notably Times Square. Wilson and Goodman’s ad, coupled with Giuliani’s success in lowering the crime rate, resulted in the mayor becoming the first Republican mayor of New York to secure a second term since 1941, with a whopping 17 percentage point victory margin to boot.

As Giuliani’s second term began winding down, Wilson joined the administration in September 1999 as a policy adviser. Although little is known about his tenure within City Hall, Wilson’s position drew scrutiny, especially as Giuliani was gearing up his bid for the United States Senate. The mayor’s senatorial ambitions, however, faltered in May 2000 amid a cancer diagnosis and revelations that he engaged in an extramarital affair.

After Giuliani’s campaign ended, Wilson returned to Tallahassee, Florida, where local records show he has owned a home since at least 1998. In June 2002, Wilson launched his own consulting firm called Intrepid Media, according to incorporation records filed with Florida’s Department of State.

It is unclear exactly how much work Intrepid received after its launch. A search of Federal Election Commission (FEC) filings indicates the group did not begin getting paid by candidates for its services until February 2004.

Around the time of Intrepid’s launch, Wilson stirred national headlines and further burnished his political credentials by creating a controversial ad for Saxby Chambliss, the then-GOP’s nominee for U.S. Senate in Georgia. At the time, Chambliss, a sitting congressman, was running against incumbent Sen. Max Cleland, a moderate Democrat who had lost both legs and his right forearm while serving as an Army captain in Vietnam.

The 2002 race between Cleland and Chambliss was noted for its harshly negative tone. The campaign, taking place only months after the tragedy of September 11th, was fought mainly on the issue of national defense. Cleland, who had voted for the Iraq war authorization act but had opposed other homeland security initiatives by the George W. Bush administration, was painted by Republican opponents as weak in the face of global terrorism.

An ad created for Chambliss by Wilson drove that point home in the final weeks of the campaign. The ad, which has been cited as one of the most negative of the past two decades, flashed photos of Osama bin Laden and Saddam Hussein across the screen before claiming Cleland was “misleading” the public about his support for homeland security.

“As Americans face terrorists and extremist dictators, Max Cleland runs television ads saying he has the courage to lead,” the ad stated, proceeding to list elven votes, mainly amendments, the senator took opposing the George W. Bush administration.

The ad helped Chambliss defeat Cleland by nearly seven points when most polls, even those taken only days before the election, had the incumbent leading. The ad’s negativity, however, tarred Chambliss for years to come, with even the late Sen. John McCain lambasting it as “worse than disgraceful.”

While Wilson’s role in creating the ad is self-acknowledged, it remains uncertain if he was paid for his services through Intrepid. FEC reports for Chambliss’s 2002 race do not provide much detail in terms of itemized expenditures, although they do note the lawmaker spent upwards of $9 million on the campaign.

A clearer picture of Wilson and Intrepid’s work begins to emerge after the Georgia Senate race. In 2004, Intrepid was hired for media consulting on two congressional races, one in upstate New York and the other in Kansas. The latter campaign was that of Kris Kobach, the fiercely pro-Trump former Kansas secretary of state and 2018 GOP gubernatorial nominee.

FEC records indicated that in 2004 Wilson was advising Kobach not just on media, but also on political strategy in his bid for Kansas’ 3rd congressional district. The race drew national attention for the heated attacks exchanged between Kobach and incumbent Democrat Dennis Moore. Kobach accused Moore of being “radically liberal,” while the incumbent congressman claimed his opponent’s position on restricting immigration was “extremist.” On election day, Moore was reelected by a large margin.

Wilson’s career seemed to lull a bit after the 2004 elections. FEC records, one of the only ways to ascertain Intrepid’s activities since as a private entity it does not have to release its financial records, indicate Wilson took on only one federal client in October 2006, the Republican Party of Wisconsin, which paid him a one time sum of $16,000 for “political consulting.”

It is unclear if he was advising state and local candidates at the time. If so, it was not in Florida as he told the Tampa Tribune in June 2006 he was unaffiliated with any race taking place that year. Similarly, Wilson seemed not to be working for any campaign throughout 2007. In the few rare media interviews he gave that year, mostly criticizing McCain’s White House ambitions, Wilson was identified as an ex-Giuliani strategist, but was not mentioned as being involved in the former mayor’s own presidential campaign.

Regardless, FEC filings indicated that between November 2006 and the end of July 2008, Intrepid was not listed as a payee of any federal candidate or political group. It is unclear if either Wilson or Intrepid have or had other avenues of revenue, like corporate clients or other entities that do not require disclosure under federal election law. Wilson has been notoriously protective of his client list, refusing many times over the years to publicly reveal who may be paying him.

Around this time, Wilson appears to have begun experiencing financial difficulties. In July 2007, he and his wife took out a $200,000 mortgage from JP Morgan Chase on their Tallahassee home. Less than a year later, in April 2008, JP Morgan attempted to foreclose on that mortgage, a legal action usually taken when the borrower stops making payments on the loan. It is unclear if that was the reason for JP Morgan’s action.

The case was voluntarily dismissed in October 2008 by JP Morgan.

The dismissal coincided with Wilson’s professional reemergence. Starting at the end of July and running through the end of September, Intrepid was paid $16,000 in four installments by the Republican Party of Wisconsin for its services. Simultaneously, Wilson took on the American Family Business Institute as a client, receiving two lump sum payments totaling $65,000 between August and September of 2008. The exact nature of Wilson’s work with the group, which is focused on repealing the federal estate tax, is unknown.

At the same time, Wilson took on a handful of smaller clients, including the Vermont Republican Committee and the National Republican Trust PAC. It was with the latter group that Wilson made his debut on the national stage by creating an ad attacking then-candidate Barack Obama for a series of controversial sermons that his pastor, the Rev. Jeremiah Wright, delivered over the years. The ad, as was the case with Wilson’s prior work, was noted for its negativity.

Before the end of the 2008 campaign, Wilson would produce other ads lambasting Obama for a series of hot button issues, most notably the candidate’s one time support for granting driver’s licenses to illegal aliens. For his services, Wilson was paid more than $40,000 by the National Republican Trust.

Money, though, was not the primary benefit from Wilson’s work for the group. After the 2008 campaign, Wilson drew notice as a national political strategist with specific insight into how to craft not only a successful but memorable negative ad.

Wilson’s growing reputation, however, did not automatically lead to more business for Intrepid.

Between the start of 2009 and the end of 2012, the company failed to line up major political candidates as clientele, despite big GOP victories across the board in 2010.

In fact, FEC records show that Intrepid’s biggest client between those four years was not a presidential campaign, but rather Adam Hasner, a local Florida elected official who made an unsuccessful run for Congress in 2012. In total, Hasner paid Intrepid more than $29,000 throughout that election cycle.

The situation hardly improved in the years following. In 2014, another stellar year for Republicans nationwide as the GOP retook the U.S. Senate that year, Intrepid was only paid a total of $34,280 by four federal groups and candidates.

Wilson’s sparse income through the company could help explain tax issues that came to a head for him that year. In February 2014, the Internal Revenue Service (IRS) filed a lien against Wilson and his wife for more than $389,000 in unpaid income taxes dating back to 2004.

To date, the lien is still in effect and has not been released by the IRS. A further tax lien for more than $780, pertaining to income earned in 2014, was assessed against Wilson and his wife in December 2015. That lien, however, was released in March 2016, with the IRS stipulating the Wilsons had satisfied the amount owed.

Soon after his financial troubles with the IRS began, Wilson had begun forging a different political role for himself, one outside the shadows of campaign work. Starting in March 2015, Wilson began branching out from just being a good source of copy for journalists to writing editorials and articles himself.

One of the earliest pieces that he penned was in Politico magazine urging his fellow Republicans to steer clear of “Hillary Clinton’s email fiasco.”

At the time, Wilson claimed he was only helping illuminate the contours of the 2016 race, before eventually being hired by one of the White House hopefuls.

“Now I’ve got latitude. Inside a campaign I will conform,” he told The Washington Post around the time his piece in Politico was published.

Despite the confidence, the work never materialized. FEC records show that Wilson’s only client throughout 2015 was then-Florida Lt. Gov. Carlos Lopez-Cantera, who at the time was vying for the Senate seat Marco Rubio was set to vacate, and the candidate’s affiliated Super PAC.

Meanwhile, Wilson was bolstering his credentials as an opponent of Trump both on social media and during in-person interviews. In September 2015, Wilson penned another piece in Politico magazine, pushing Trump’s rivals to utilize an upcoming Republican debate to end his candidacy.

“Overall, go out there tonight, swing for the fences, smile, laugh, have some fun,” Wilson wrote, after outlining what he saw as the New York billionaire’s weak points for rivals to target.  “You could be living on a diet of lead paint, cheap vodka and Real Housewives and still know more than Trump does about, well, everything.”

Even as Wilson’s profile as a prominent Trump critic was growing, so were his financial issues. In April 2016, Wilson had a judgement filed against him in Florida circuit court by American Express for defaulting on more than $25,000 in credit card debt. In August of that year, American Express received a writ of garnishment against Wilson in hopes of recouping its money.

The trouble continued for Wilson throughout August as Citibank sought to foreclose on his home, again, possibly because of inability to pay a mortgage owed to the financial giant. Unlike the prior foreclosure attempt by JP Morgan in 2008, this case was not dismissed. It appears to be still active, suggesting that Wilson has obtained an arrangement with the bank to pay the amount of owed.

As this was occurring, Wilson finally made his debut as presidential campaign strategist for Evan McMullin, a former CIA operative running as a vocal Never Trumper. Although the timeline of the affiliation is unclear, McMullin’s first payment to Wilson came six days after Citibank filed its foreclosure notice in Florida Circuit Court.

Overall, Wilson would be paid more than $35,000 by McMullin via both himself and Intrepid through November 2016.

McMullin’s campaign, however, failed to ever get off the ground. Initially, many had believed McMullin would be an enterprising candidate for Republicans opposed to Trump’s unorthodox platform and personality. By Election Day, though, such hopes had evaporated, with the former CIA operative only putting up a strong showing in his home state of Utah.

Even as McMullin’s time in the spotlight was fading, Wilson’s national profile was just forming. Following the election, the strategist stepped up his Never Trump criticism, garnering not only bylines in some of the country’s most reputable media outlets, but also appearing frequently on network television.

His notoriety as a Trump opponent even helped land a gig as an editor at large at the Daily Beast despite little background in conventional journalism and two book deals. The first book, titled Everything Trump Touches Dies: A Republican Strategist Gets Real About the Worst President Ever, was a New York Times bestseller when it debuted in August 2018.

Its publication occurred the same month that American Express released its more than $25,000 judgement against Wilson for unpaid credit card debt.

Similarly, Wilson’s position as Never Trumper seemed to translate into a benefit for his media company. Between 2017 and 2018, Intrepid was paid more than $116,000 by Kurt Jetta, a Trump critic who was vying for the Republican nomination for Florida’s 21st Congressional District. Jetta eventually dropped his bid after failing to make headway with the local GOP grassroots.

Wilson did not reply to a comment request for this story.

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