Widely described by news outlets as a far-right politician,[3][4][5][6][7][8] he was the Republican nominee for the 2022 Illinois gubernatorial election, which he lost to incumbent Democrat J.

[9] Bailey ran in the Republican primary for the 12th congressional district in the 2024 U.S. House elections, narrowly losing to incumbent Mike Bost.

[2] He graduated from North Clay High School and earned an Associate of Science degree in agricultural production from Lake Land College.

[15] In a rare victory for candidates supported by Dan Proft's Liberty Principles PAC,[16][17] Bailey defeated David Reis in the 2018 Republican primary.

[20][21] On July 8, 2019, Bailey announced his intention to run for the Illinois Senate seat being vacated by Dale Righter.

B. Pritzker, claiming that the governor's stay-at-home order extension to mitigate effects of the COVID-19 pandemic was unfairly affecting residents of Clay County.

[33][34][35] On December 13, 2021, Bailey announced that his running mate for lieutenant governor would be former WLS-AM 890 talk radio host Stephanie Trussell.

[43] In 2023, Bailey announced that he would run against incumbent U.S. Representative Mike Bost in the Republican primary for the 12th congressional district in 2024.

[45][47] In a video posted on Facebook in 2017, Bailey said "the attempted extermination of the Jews of World War II doesn't even compare on a shadow of the life that has been lost with abortion since its legalization".

[50] In 2019, Bailey and seven other Republicans sponsored a resolution calling for the City of Chicago to become its own state, claiming that "the majority of residents in downstate Illinois disagree with City of Chicago residents on key issues such as gun ownership, abortion, immigration, and other policy issues.