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Trump Backs Darren Bailey In Illinois Rematch

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Published on May 20, 2026
Trump Backs Darren Bailey In Illinois RematchSource: Daniel Torok, Public domain, via Wikimedia Commons

Donald Trump stepped back into Illinois politics on Tuesday, publicly backing Republican Darren Bailey in the governor’s race and turning a 2022 rerun into must-watch November drama. The former president’s endorsement instantly ratchets national attention back onto a contest Democrats say is a top priority this fall.

According to FOX 32 Chicago, Trump used a public appearance to make his support for Bailey crystal clear and again took aim at Gov. J.B. Pritzker. The station’s The Chicago Report posted video of the remarks on Tuesday, underscoring that the former president has returned his gaze to the Illinois matchup.

Rematch set for November

Darren Bailey clinched the Republican nomination in March, setting up a rematch with Gov. J.B. Pritzker after losing to him in 2022, according to the Chicago Sun-Times. Pritzker’s team quickly cast Bailey as too extreme for the state, and the governor warned voters that the general election would be “the fight of our lives,” NBC Chicago reported.

Trump's history with Bailey

Trump first endorsed Bailey during the 2022 cycle, a relationship that helped lift Bailey to the GOP nomination that year, according to NPR Illinois. The new endorsement brings that national spotlight back at a moment when both campaigns are sharpening their messages for the general election.

Bailey courts Chicago voters

Bailey has recently tried to broaden his appeal in the Chicago area, renting an apartment on the Near South Side to serve as a local campaign base, quietly planting a flag on the South Side. Campaign strategists say that winning more suburban and Cook County support will be critical, a point highlighted in post-primary analysis that warned Bailey needs a different coalition this time, according to Axios.

What comes next

The endorsement gives Bailey an early headline and could help mobilize national volunteers and donors, but analysts note he still faces a sizable fundraising and turnout gap in heavily Democratic parts of the state. Observers say the race will likely turn on suburban turnout and whether Pritzker can keep his fundraising advantage, a dynamic that favored the governor in 2022, the Chicago Sun-Times reported.