Veteran lobbyist with clients that regularly intersect with City Hall weighs run for Chicago mayor
Mayor Brandon Johnson, as is widely known, has personal and political entanglements with one of the more powerful special interests around, the Chicago Teachers Union.
One of his likely challengers in the 2027 mayoral election, longtime lobbyist John Kelly, would have to deal with his own potential conflicts of interest if elected, largely because a number of his existing lobbying clients intersect with City Hall, and might also down the road.
Among them: the White Sox, for whom Kelly works as a contract lobbyist at the state government level. The team has made clear it wants taxpayers to subsidize a new stadium complex.
The team’s principal owner, Jerry Reinsdorf, is also a business partner with Kelly in a local security firm whose executives include James Smith, a former federal agent whose wife Margaret Houlihan Smith is a lobbyist for United Airlines. Hubbed at O’Hare Airport, the Chicago-based carrier negotiates with City Hall for, among other things, gate space, since the city government owns and operates the airfield.
Kelly is also a state lobbyist for the United Center, overseen by a partnership between the Reinsdorf family that also owns the Bulls and the Wirtz family that owns the Blackhawks. A massive development project around the Near West Side stadium that includes a music hall and retail space has already required some approvals from city government, with more expected in coming years.
A relative of former Cook County Assessor Jim Houlihan, Kelly also lobbies City Hall on behalf of Bally’s Corp., which operates a temporary casino in River North and is in the midst of building a permanent gambling complex in River West.
Under Johnson’s predecessor Lori Lightfoot, Bally’s was chosen for the project — Chicago’s first and only casino. More recently, Bally’s has pushed back against efforts by some members of the City Council to legalize video gambling in the city, something Johnson has been squeamish about.
Disclosure records show Kelly lobbied the mayor’s office and alderpeople for Bally’s throughout 2025.
He also is listed as a City Hall lobbyist for the Katten Muchin Rosenman LLP law firm, which was included on the city’s list of approved “outside counsel” in 2025 and has done municipal bond work for City Hall for years.
Kelly created a campaign fund in late October that’s already pulled in more than $450,000 in contributions. He hasn’t formally announced that he’s running for Johnson’s job, but says he’s already assembling “a team” to likely do so.
He said he’d handle potential conflicts by separating himself from his lobbying business, called All-Circo, Inc., though it’s unclear whether he would do so during the race or only if and when he wins.
“I would divest myself from my firm,” he said. “We’re in conversations now to make sure we do this appropriately... we’d have zero conflict of interest.”
He said he wouldn’t feel pressure to carry water for former clients.
“You have to tell a lot of people ‘no’ as mayor. Whoever comes to me when I’m mayor, a former client or not, or any business interest, I have one guiding principle: is it good for the taxpayers of Chicago?”
Lobbyists are part of the sometimes-seedy underbelly of local, state and federal government, advocating on behalf of special interests that often cynically throw campaign money at political figures.
The corruption trial of former Illinois House Speaker Michael J. Madigan exposed some of the behind-the-scenes workings of other powerful Springfield lobbyists.
Kelly said he performs his job honestly and won’t shy away from his background.
“The skillsets that I learned as a lobbyist are the same skillset you need as the mayor of Chicago to educate decision makers and to collaborate with people,” he said, adding that his knowledge in particular of state government, which City Hall is known to hit up for additional funding, is key.
“It’s definitely going to be a plus for me,” he said.
Kelly also said that, if elected, he would be comfortable working collaboratively with the federal government no matter who is in the White House. To that end, his wife Julie is a conservative social media figure regularly putting out content favorable to President Donald Trump, something potential opponents are likely to seize on given that Chicagoans skew Democratic.
Kelly identifies as a Democrat and used to be a lobbyist for the office of Cook County Board President Toni Preckwinkle — a close political ally of Johnson during his successful run for mayor in 2023 when he was a Cook County Board member. Preckwinkle also heads the Cook County Democratic Party.
The chairman of Kelly’s campaign fund, Citizens for John Kelly, is William Singer, a long-ago North Side alderman known as a rare independent voice against the first Mayor Daley, who he ran against unsuccessfully in 1975, and the Democratic machine.
Many years later, Singer was involved in a real estate deal that saw former Southeast Side Ald. Edward Vrdolyak convicted in a kickback scheme.
A Chicago law firm run by Vrdolyak’s family members contributed $14,600 to Kelly’s campaign in a donation dated Dec. 31, according to Illinois State Board of Elections records.
Kelly said he’s a longtime friend of one of Vrdolyak’s sons, who he attended Mount Carmel High School with.
Ex-Blackhawks star Chris Chelios is Kelly’s campaign treasurer, and several other former pro athletes are among the recent donors, including: former Bears greats Richard Dent and Brian Urlacher, former NBA player Charles Oakley and former Sox catcher AJ Pierzynski, records show.
All-Circo has contributed more than $500,000 to state and local political candidates and causes over the years, though Kelly wasn’t part of that business at the time of all of the donations.
Individually, Kelly has given nearly $200,000 to candidates for federal office over the last two decades, records show. Kelly has contributed more than $50,000 to state and local candidates, including members of the City Council.