2015 Chicago mayoral campaign

Wilson ran for Mayor of Chicago in 2015, being one of several challengers to incumbent mayor Rahm Emanuel.

Wilson collected 43,000 signatures for his candidature petition within five days. Emanuel issued a challenge to the validity of signatures collected.^[12] Emanuel ultimately dropped his challenge to Wilson's petition.^[13]

Wilson staked out a number of positions, including advocating for bringing a casino to Chicago and restoring Meigs Field (on Northerly Island) as an airport.^[10] Wilson was critical of Police Superintendent Garry McCarthy, and pledged to fire him if elected mayor.^[10] Wilson was also critical of Chicago Public Schools school closures which had taken place under Emanuel.^[10]

Wilson placed third in a five-candidate race with 50,960 votes, equal 10.66% of the votes cast.^[14][15][16]

Wilson's endorsement in the runoff was actively sought by both candidates Rahm Emanuel and Jesús "Chuy" García.^[17] Wilson endorsed García.^[18][19]

2016 U.S. presidential campaign

Wikimedia Commons has media related to Willie Wilson.

After setting up an exploratory committee on May 11, 2015, Wilson officially announced on June 1, 2015, that he would be running as a candidate for President of the United States in the 2016 election. He ran as a Democrat.^{[2][21][22][23]}

The Wilson campaign was the first presidential campaign, Democratic or Republican, to buy advertisements in the state of Iowa.^[24]

Wilson was on the ballot in several states during the 2016 Democratic primaries. He was the only minor candidate to appear on the ballot in South Carolina's "First in the South" primaries, perhaps due to the comparatively higher cost of the state's ballot entry fee.^[25] Wilson received 1,314 votes, or 0.35% of the total, in South Carolina, placing ahead of Former Maryland Governor Martin O'Malley. Wilson dropped out on April 12, 2016.^[26]

In the general election, Wilson voted for Republican nominee Donald Trump.^[27]

2019 Chicago mayoral campaign

In March 2018, Wilson formally announced that he would run a second time for Mayor of Chicago in the 2019 mayoral election.^[28]

During his campaign, Wilson generated controversy for handing out money to churchgoers. This practice of his was challenged before the Illinois State Board of Elections, which found that it did not violate any campaign finance laws since the money came from his non-profit foundation. Wilson defended his actions, declaring that his church appearances were not campaign-related, and that he was not buying votes.^[29] He continued this practice after the decision by the Board of Elections.^[30]

During the campaign, in late November 2018, Wilson declared that he believed that other black candidates needed, "to get out of the way."^[31]

Wilson launched challenges to the candidature petitions of several black candidates,^[31] including Roger Washington,^[31] Ja'Mal Green,^[31] Neal Sales-Griffin,^[32] and Dorothy Brown.^[32] At the last minute, Wilson moved to drop his challenge to Sales-Griffin's and Brown's petitions. Brown was still removed from the ballot due to Toni Preckwinkle maintaining her challenge to Brown's petition, but Sales-Griffin was allowed to be included on the ballot.^[32] Chicago Electoral Board Chair Marisel Hernandez chastised the Wilson campaign for its political maneuvers regarding ballot challenges.^[32]

Wilson was endorsed by the Cook County Republican Party.^[33]

Wilson failed to make it to the runoff, placing fourth with 59,072 votes, equal 10.61% of vote cast.^[34][35][36] Wilson performed very well on the West and South sides of the city.^[37] Despite placing fourth, Wilson had a plurality of the vote in more wards than any other candidate (he came first in thirteen wards).^{[36][38][39][40]} The thirteen wards that Wilson carried a plurality of the vote in were all predominately black (these being thirteen out of the total of eighteen wards in the city that are predominately black).^[41]

Again, Wilson's endorsement was actively sought by both candidates in the runoff.^[42] Wilson endorsed Lori Lightfoot.^[43][44][45]

2020 U.S. Senate campaign

In August 2019, Wilson expressed his intention to challenge incumbent United States Senator from Illinois Dick Durbin in 2020, running in the general election as an independent challenger to Durbin.^[46] Rather than run as an independent, he ultimately opted to run under the ballot line of his newly created "Willie Wilson Party".^[47]

Wilson received the support of three current and former Chicago aldermen, as well as that of the Fraternal Order of Police.^[48]

Wilson received 4% of the vote statewide, finishing in a distant third place. His highest support came from the majority-black wards of Chicago where he had done well in both his mayoral campaigns. Totaling up all 18 of Chicago's majority-black wards, Wilson garnered 18.5% of the vote, well ahead of Republican Mark Curran, who received only 4%, but still far behind Durbin who received 75.9%.^[48]

2023 Chicago mayoral campaign

Wilson launched a third campaign to become the Mayor of Chicago. Wilson is running as an independent, as Chicago hosts non-partisan elections. In the winter, Wilson donated various resources to combat the COVID-19 pandemic. In response to high inflation, Wilson organized various gas giveaways^[49] and food donations.^[50]

Wilson’s campaign cited key issues in his platform as being small businesses, increasing safety, and ‘rebuilding’ Chicago.^[51] Wilson advocated for increased safety on public transport,^[52] crime reduction, tax reduction,^[53] and opposing corruption. He also supported the abolishment of red-light traffic cameras,^[54] parking meter reform,^[55] and other issues.

Wilson accused incumbent mayor Lori Lightfoot of mismanagement, especially relating to gas prices and economic reinvigoration. He also called out corruption in the city, and said some officials were “out of touch” with the public.^[56] Wilson criticized earlier decisions to implement previous safety measures amid the COVID-19 pandemic that had the impact of temporary prohibiting church gatherings.^[57]

Describing himself as "pro policeman", Wilson stood in opposition to rules and regulations that he regards as hindering the police's ability to combat crime. At one mayoral debate, Wilson declared that the city should, "Take the handcuffs off the policy, [sic] put them on people that's actually doing [crime]," and that those who flee police should be, "hunted down like rabbits".^[58] Wilson spoke positively of the Chicago Police Department.^[57]

Wilson was considered to be the only of the nine candidates on the ballot not to be affiliated with the Democratic Party, though the election is officially nonpartisan.^[59]

In the initial round of the election, Wilson was defeated, placing fifth of nine candidates with 49,248 votes (9.57% of the election's overall vote). A week after the first round, Wilson subsequently endorsed Paul Vallas in the runoff election.^[60]

Economic policy

Wilson stated in 2019 that he believes the spending of tax money has "not proportionately benefited all races of citizens," in Illinois.^[27]

LGBTQ rights

Wilson tweeted in response to the Obergefell v. Hodges decision, “I disagree with what I consider the Supreme Court’s reinterpretation of what constitutes marriage. Marriage has and should always be that sacred union between a man and a woman. Period."^[63] However, in 2018, Wilson declared that he had changed his mind on the issue of same-sex marriage, declaring that he now believes that, "everybody is entitled to do whatever they want to do and be with whoever they want to be."^[63]

In a 2018 interview with the Chicago Sun-Times, Wilson stated that his upbringing in the Deep South had made it difficult for him to understand the LGBTQ community, but that he was "reaching out" and seeking to "learn".^[63]

Mayoral

2016 Democratic presidential primaries

A.^ On ballot as other

B.^ Counting Uncommitted as having placed 3rd

C.^ Counting Uncommitted, No Preference, and scattering, respectively, as placing 4th, 6th, and 7th

United States Senate