Wilson entered the political arena by campaigning for
Connie Mack during the
1988 Florida Senate election. Later, he served on the
George H. W. Bush campaign as Florida field director. Wilson played a significant role in the
2002 United States Senate election in Georgia, in which
Saxby Chambliss was facing
Democratic Senator
Max Cleland, a disabled Vietnam veteran and recipient of the
Silver Star. Wilson helped create an ad that attacked Cleland's voting record concerning the nascent
Department of Homeland Security, flashing images of
Osama bin Laden and
Saddam Hussein, with some observers suggesting that it questioned Cleland's patriotism. In an interview with
HuffPost, Wilson stated that he thought that "DHS was on the front line against Osama bin Laden". As Wilson reflected in 2016, "The Cleland ad was powerful because it went to his strengths [...] Everyone assumed Cleland was immune to critiques on national security issues. [...] they didn't calculate that I have no moral center when it comes to political ads, and I will destroy the innocent and the guilty". Following Cleland's death in 2021, Wilson received criticism from journalists such as
Glenn Greenwald and
Charlie Pierce. In 2012, Wilson posted to Instagram an image of a cooler emblazoned with a Confederate battle flag and the words "The South Shall Rise Again", prompting allegations of racism. After public backlash, Wilson eventually deleted the post. It resurfaced in 2020 while The Lincoln Project was airing television ads attacking the public display of that flag. In January 2020, Wilson appeared alongside CNN anchor
Don Lemon and CNN contributor Wajahat Ali in which they discussed an exchange between United States Secretary of State
Mike Pompeo and NPR reporter Mary Louise Kelly. During this segment, Wilson made comments about Trump supporters, stating they were "part of the credulous
boomer rube demo". He employed the tone of
Southern American English in the segment for emphasis. Wilson has been known to use extremely crude language and generalizations, such as, when criticizing supporters of Donald Trump during an interview with MSNBC leading up to the 2016 presidential election, he called them "childless single men who masturbate to anime". In June 2020, Wilson tweeted a response to a 2012
Domino's Pizza tweet thanking
White House Press Secretary Kayleigh McEnany, then a college student, for her opinion that Domino's pizza was superior to pizza from New York. In his tweet, Wilson declared, "You just killed your brand." This later prompted a response from Domino's Pizza's official Twitter account, saying "Welp. It's unfortunate that thanking a customer for a compliment back in 2012 would be viewed as political. Guess that's 2020 for ya." According to
The Daily Dot, "Domino's response immediately went viral", however, they credited Wilson for not deleting the tweet "despite the unrelenting onslaught of mockery" directed at him. == Media ==