President Donald Trump says he’s “all for Bailey” once again in the Illinois governor race, handing Republican firebrand Darren Bailey an endorsement that’s unlikely to do the former downstate legislator many favors as he tries to court Chicago-area moderates in his rematch against incumbent Democratic Gov. JB Pritzker.
Speaking to reporters Sunday before returning from a trip to Ireland, Trump said of his longtime supporter: “I’ve already endorsed him. I’m all for Bailey.”
Bailey rallied alongside Trump in 2022 before losing to Pritzker by nearly 13 percentage points, and Bailey credited Trump with inspiring him to stay in the 2026 race in the face of immense tragedy last fall after Bailey’s son, daughter-in-law and two grandchildren died in a helicopter crash.
“Bailey is a very good candidate,” Trump said. “He had a horrible tragedy. It’s amazing that he can go forward. A large portion of his family was wiped out.”
But Bailey has largely distanced himself from the president while focusing on crime, education and economic issues in his latest gubernatorial campaign.
The GOP nominee’s team scarcely publicized his trip last week to Dallas for the Republican Midterm Convention, where he sat in the president’s box near downstate U.S. Rep. Mike Bost — who carried Trump’s endorsement while staving off a 2024 congressional primary challenge from Bailey.
Hello from the President’s Box at the Midterm Convention! Thank you for the invitation, President Trump! pic.twitter.com/DrHj4nBqpO
— Mike Bost (@BostForCongress) September 11, 2026
Meanwhile, Bailey has gone out of his way to publicize his differences in opinion with Trump.
In April, Bailey said the president “was wrong” to criticize Pope Leo XIV and urged him to apologize to the Chicago-born pontiff. And last month, Bailey said he doesn’t “see eye to eye” with Trump’s support of data center expansion.
It’s a logical campaign strategy for the downstate farmer who is trying to make inroads with suburban voters who rejected him by 20 percentage points or more last time around, in areas that long served as the Illinois GOP base before defecting from Trump.
That leaves a tight rope to walk for Bailey and his downstate, rural base that remains staunchly in Trump’s corner.
“I appreciate President Trump’s endorsement of my campaign for governor, but that’s not what this race is about; it’s about the endless ways JB Pritzker has failed Illinois families over the last eight years,” Bailey said in a statement.
“From endless tax hikes to the highest property taxes in the nation, preferential treatment for career criminals while our officers are underpaid and under appreciated, all while businesses shutter their doors and everyone from workers to the Chicago Bears vote with their feet, our state is worse off today under JB Pritzker’s leadership. Change will only happen when Illinois voters step into the voting booth and vote for it,” he said.
Pritzker’s campaign has sought to remind voters of Bailey’s ties to Trump at every turn.
“Just a few days after Darren Bailey returned home from Trumpapalooza, Donald Trump endorsed Bailey and sang his praises,” Pritzker campaign spokesperson Leah Hurwitz said in a statement. “This won’t come as a surprise to Illinoisans who know all about Bailey’s intense admiration for Trump. Despite the damage the president has done to our state, Bailey still supports Trump’s tariffs, cheered on his invasion of federal agents in our streets, and vowed to ‘roll the red carpet out’ for him.”
Pritzker’s team raised the question of whether Trump will campaign with Bailey next week, when Trump is scheduled to return to the Chicago area for the first time in his second term to chair the Presidents Cup golf tournament at Medinah Country Club, running Sept. 22-27.
Pritzker, who is considering a 2028 run for president, has raised his national profile as a vociferous Trump opponent.
“I think JB Pritzker’s a disaster as a governor,” Trump said. “You look at what’s happening with crime — JB Pritzker should lose. For some reason, Democrats win there, I don’t know why.”