Bailey Admits Calling Chicago a 'Hellhole' Was 'Dumb' as He Courts Urban Voters

The GOP gubernatorial candidate is trying to attract more support in Illinois' largest city after losing it by a wide margin in 2022.

Apr. 19, 2026 at 6:21pm

Got story updates? Submit your updates here. ›

A photorealistic painting of a solitary hot dog cart on a Chicago street corner, with warm sunlight casting deep shadows across the scene, capturing the quiet, cinematic mood of the city.As Bailey courts urban voters, his campaign's nostalgic imagery evokes the city's iconic food culture and streetscapes.Chicago Today

Darren Bailey, the Republican nominee for Illinois governor, has expressed regret for previously calling Chicago a 'hellhole' as he seeks to win over more urban voters in his rematch against incumbent Democratic Gov. JB Pritzker. Bailey is distancing himself from some of the more extreme rhetoric of former President Trump and the national GOP in an effort to appeal to a broader statewide electorate.

Why it matters

Bailey's 2022 campaign was hampered by his poor performance in the heavily Democratic city of Chicago, where he lost by over 50 points. As he tries again to unseat Pritzker, Bailey is working to soften his image and attract more support from urban and suburban voters across Illinois.

The details

In a new social media video, Bailey and his running mate Aaron Del Mar toured Chicago, tried local food, and Bailey acknowledged his previous 'hellhole' comment was 'dumb.' Bailey has also distanced himself from some of former President Trump's more extreme rhetoric, criticizing Trump's recent attacks on the Pope and a GOP social media post mocking Pritzker's weight.

  • In 2022, Bailey routinely blasted Chicago and its Democratic leaders, calling it a 'crime-ridden, corrupt, dysfunctional hellhole' during a debate.
  • Earlier this month, Bailey said Trump was 'wrong' for attacking Pope Leo XIV and posting an AI-generated image mocking the governor's weight.
  • Bailey recently moved into an apartment on Chicago's Near South Side as part of his effort to connect with urban voters.

The players

Darren Bailey

The Republican nominee for Illinois governor, a downstate farmer who is challenging incumbent Democratic Gov. JB Pritzker.

Aaron Del Mar

Bailey's lieutenant governor running mate, from Palatine.

JB Pritzker

The incumbent Democratic governor of Illinois, who defeated Bailey by a wide margin in 2022.

Donald Trump

The former president whose rhetoric and policies Bailey has sought to distance himself from in his current campaign.

Got photos? Submit your photos here. ›

What they’re saying

“Alright Darren, what did you think of the 'hellhole'?”

— Aaron Del Mar, Bailey's lieutenant governor running mate

“Aaron listen, I said something dumb, and I am certainly not too proud to admit when I'm wrong. So, I love Chicago. I love everything this city has to offer. I can't wait to experience it.”

— Darren Bailey, Republican gubernatorial candidate

“I said things about the city I wish I could take back. But this city showed me grace anyway. I'm a better man for it.”

— Darren Bailey, Republican gubernatorial candidate

What’s next

Bailey's campaign is hoping his new outreach efforts in Chicago will help him perform better in the city and its surrounding suburbs in the November election.

The takeaway

Bailey's shift in rhetoric and campaign strategy reflects the political realities he faces in trying to unseat an incumbent governor in a state where the Democratic Party holds significant advantages, especially in urban and suburban areas.