Bailey, 56, a state senator from largely rural downstate Illinois, is running against Democratic Gov. J.B. Pritzker, who is seeking his second term. He represents a sharp contrast to the past three Republican Illinois governors, who have won by flexing fiscal conservative values and advocating for business-friendly policies, while remaining relatively moderate on social issues.
By contrast, Bailey, who has the endorsement of former president Donald Trump, frequently quotes Scripture in public and supports a total ban on abortion. He earned his reputation as a provocateur within his party for sponsoring legislation to separate Chicago from the rest of the state.
While his hard-right rhetoric and positions helped Bailey in the primary, they are unlikely to help in a general election where Republicans need to peel away voters from Chicago and its five collar counties. That turf controlled by Democrats is denser in population and more racially and ethnically diverse than more rural regions of Illinois, where the population tends to be either stagnant or shrinking. Biden only needed to win 14 of the state’s 102 counties to beat Trump by 17 percentage points in 2020.
John Jackson, a political scientist at Southern Illinois University in Carbondale, said Bailey needs to “appeal to independents and Republicans who are more moderate and not prone to getting on board automatically with him.” While Trump’s endorsement helped tip a contentious six-person primary in his favor, Jackson said “it’s not nearly enough” to win the general election.
Bailey, who operates a large family farm that produces corn, wheat and soybeans in downstate Xenia, located about 250 miles from Chicago, is more in his element when talking to voters far outside the city. Addressing a crowd of farmers in rural McLean County last month, Bailey described Chicago in almost apocalyptic terms. He compared it to “the O.K. Corral with shootouts and homicides every night.” At a campaign event this month, he called Democrats Pritzker, Chicago Mayor Lori Lightfoot and Cook County State’s Attorney Kim Foxx “the Three Musketeers of crime, chaos and tragedy in the city of Chicago.”
This month, he also staged impromptu media events at sites of gun violence in an effort to suggest that Democrats don’t care about victims and to present himself as an outside catalyst for change. In one exchange with a reporter, however, he admitted to living in one of Chicago’s most prominent high-rises. He said he wanted to “immerse” himself in the city’s “culture.”
Pritzker has portrayed Bailey as too extreme for Illinois. During the primary, Pritzker and the Democratic Governors Association spent $30 million in ads attacking a moderate Republican mayor from the Chicago suburbs. Critics said the governor wanted to ensure that Bailey would be his general election opponent.
Bailey and Pritzker have agreed to two debates in October.
The governor has cited comments Bailey made in a 2017 Facebook video, in which he said the Holocaust “doesn’t even compare” to abortion, a comment that many faith leaders blasted as insensitive. In August, Bailey doubled down, telling a radio interviewer that “the Jewish community themselves” told him he was right, without specifying which congregations he consulted. Hours after a gunman killed seven people and critically injured two dozen others on the Fourth of July in Highland Park, a suburb north of Chicago, Bailey posted a Facebook video in which he praised law enforcement and told viewers to “move on and let’s celebrate the independence of this nation.”
Bailey’s defense of those remarks has dominated several news cycles since he won the primary in June and has made some top Republicans nervous. At a Republican gathering at the Illinois State Fair in August, state Rep. Jim Durkin, House Republican leader, would not say if he supported Bailey. Instead he emphasized the party’s goal of picking up seats to reduce the stark disadvantage to Democrats, who hold a 73-45 majority in the House and a 41-18 majority in the Senate.
Illinois Republican Party Chairman Don Tracy said Bailey is a “really genuine guy” who is “not a polished politician.” That image is also key to his appeal, especially downstate where Bailey is a member of the so-called “Eastern Bloc” of Republican state legislators who opposed Pritzker’s Covid-19 policies.
Bailey, who has served in the legislature since 2019, came to prominence in 2020 when he filed a lawsuit against Pritzker, claiming the governor had exceeded his legal authority when he issued a stay-at-home order at the beginning of the pandemic. When the Illinois General Assembly met in person in May 2020, Bailey was the lone holdout who refused to wear a mask, a decision that forced a vote to physically remove him from the proceedings.
The moment solidified Bailey as a fighter, said Tracy.
“For those of us who thought lockdowns without legislative involvement were either a bit excessive or overly wrong, he was one of the few people who was really willing to stand up and fight that,” Tracy said. “That gave him not just publicity, but a reputation for someone who was willing to speak truth to power.”
Bailey’s early momentum is tied to Trump, who appeared with him at a rally the weekend before the primary. But since then Bailey has largely avoided answering reporter questions about the former president. In a recent radio interview, however, Bailey said that the FBI raid on Trump’s Mar-a-Lago resort was “very upsetting” and made him “very concerned about the future of our country.”
Bailey is part of a wave of Illinois Republicans who scored primary wins over more moderate rivals. Kent Redfield, a professor emeritus with the University of Illinois and the Institute for Government and Public Affairs, said these victories are largely due to an energized base of grass-roots activism among Trump supporters and a moderate wing of the GOP “that’s been in decline” in recent years. Redfield said that top Republican leaders who supported moderate candidates are now concerned that their original goal of breaking their party’s super-minority status in the General Assembly has become even more of an uphill climb.
“The intention was to reestablish credibility, increase numbers in the legislature, and rebuild their funding base. I don’t think having Bailey on the top of the ticket is helping with that,” Redfield said. “Now, Republicans are in a place where instead of being in expansion mode, it may be survival.”
Tracy, the state GOP chair, said that Trump “is going to be a factor” in the election, but not as much as elsewhere in the country. He said that Illinois Republicans win when they focus less on Trump and more on what they perceive as failures of the Biden administration and “what happens when you walk away from common-sense” economic policies and toward “progressive socialist ideas.” Pritzker, he said, is vulnerable on issues voters care about like crime and high gas and grocery prices. He dismissed measures Pritzker instituted, like a gas tax freeze and suspension of the grocery tax, as “election-year gimmicks.”
Steve Boulton, chairman of the Chicago Republican Party, said Bailey’s opportunities are with minority communities in Chicago and its suburbs who tend to be more conservative on social issues and are those most affected by inflation and crime. This is especially true for Black Chicagoans, whose population has shrunk by nearly 33 percent since 1980. “The Democratic ethos is not working anymore for them,” Boulton said.
Bailey marched in a prominent South Side parade in August and his running mate, former conservative talk show host Stephanie Trussell, is Black and a Chicago native. She also has come under fire for recent anti-gay social media posts.
Boulton says voters shouldn’t be misled into believing Bailey is a Trump acolyte. “What’s emerging in the Republican Party is not anti-government, it’s smarter government,” he said. “Darren Bailey signs on with that.”
