Republican gubernatorial candidate Darren Bailey paid for a video billboard truck to circle McCormick Place in Chicago on Friday, using the opening of the Socialism 2026 conference at the Hyatt Regency Chicago to hammer Governor JB Pritzker two months before their November rematch. Bailey appeared outside the hotel himself, arguing that the governor has spent nearly eight years promoting the same policies embraced by the conference's organizers.
As reported by WLS-TV, Bailey said “socialists feel at home in Illinois” and accused Pritzker of enabling that comfort through nearly eight years in office. He framed the November election as a choice between what he called “an out-of-touch billionaire and working Illinoisans,” and argued that more government spending and higher taxes do not solve the state's economic problems. Bailey said he is working to expand the Republican coalition and hopes the spectacle outside the conference will prompt voters to reconsider backing another Democratic term for governor.
The choice of venue gave Bailey's attack an extra edge. The Hyatt Regency Chicago is connected to Pritzker family business interests, since the Hyatt Hotels Corporation was built starting in 1957 by the governor's father, Donald Pritzker, and his uncle Jay Pritzker, according to Forbes, which pegged JB Pritzker's personal net worth at $3.9 billion in March. Bailey's campaign has leaned into that contrast as the race has become a referendum on wealth and spending, with Pritzker having already poured $65 million of his own money into his reelection bid by August, as Hoodline reported in its coverage of the Illinois State Fair.
A Conference With More Than 2,600 Attendees
Socialism 2026, organized by the Chicago-based independent publisher Haymarket Books, scheduled more than 100 workshops and panels at the Hyatt Regency from Thursday through the holiday weekend, per organizers. Registration ran from a standard $155 ticket up to a $500 sustainer rate, and the event drew more than 2,600 registered attendees, according to conference organizers. Programming this year includes a session from streamer Hasan Piker on abolishing the Senate, prisons, police and borders.
Conference organizer Sean Larson said the group backs Medicare for All, free healthcare and free childcare, and organizers said they plan to fund those proposals by taxing wealthy people. Socialism 2026 organizers defended the conference platform amid the outside criticism, according to the same WLS-TV account. Pritzker himself has not embraced the socialist agenda promoted at the conference, and has instead described Democrats as a “big tent” party.
Conservative Groups Join the Protest
Bailey was not alone outside the Hyatt. The conservative advocacy group Americans for Prosperity sent its own billboard truck past the hotel, with Illinois deputy state director Brian Costin saying the organization has concerns about the conference. Americans for Prosperity has also run mobile billboard campaigns this summer targeting Pritzker over proposed toll rate increases and state spending, as Big Country News reported in August.
The Pritzker campaign dismissed Bailey's criticism, saying he wants to talk about anything but his own record, which it described as extreme. The dueling statements underscore how the governor's race has turned socialist ideas within the Democratic Party into a flashpoint, even though Pritzker has not adopted the platform being debated inside the conference.
A Campaign Rooted in a Chicago Comeback Bid
Bailey's appearance outside the Hyatt is part of a broader push to improve on his 2022 showing in Chicago, where he lost to Pritzker by 12.5 percentage points statewide and captured only about 15% of the vote within city limits. In April, he set up a Near South Side apartment as a regional campaign headquarters, an effort to soften his past description of Chicago as a “hellhole” and engage urban voters directly.
Bailey secured the GOP nomination in March with roughly 50% of the vote in a four-way primary, setting up the rematch with Pritzker. His platform has also centered on fiscal auditing, including the “Illinois DOGE” initiative he announced in January, which running mate Aron Del Mar would oversee to target state spending waste. Former President Donald Trump endorsed Bailey in May, reinforcing national Republican backing for the ticket heading into a November election that is now two months away.
