Potential Conflicts Emerge in Chicago Mayoral Race

Lobbyist John Kelly's extensive client list raises questions about his ability to govern impartially.

Jan. 29, 2026 at 9:31pm

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As Chicago Mayor Brandon Johnson's first term continues, potential challengers are already emerging for the 2027 mayoral election. Among them is John Kelly, a longtime lobbyist whose extensive client list presents potential conflicts of interest should he win office. Kelly's current lobbying work includes representing the Chicago White Sox, who are seeking taxpayer subsidies for a new stadium complex, as well as a business partnership with White Sox owner Jerry Reinsdorf in a local security firm. Further complicating matters, an executive at that firm is married to a lobbyist for United Airlines, which regularly negotiates with City Hall regarding gate space at O'Hare Airport.

Why it matters

The involvement of lobbyists in local politics is often viewed with skepticism, given the potential for special interests to unduly influence policy decisions. Kelly's extensive network of clients and connections raises questions about his ability to remain impartial if elected mayor.

The details

Kelly also lobbies for the United Center, home to the Chicago Bulls and Blackhawks, and for Bally's Corp., which is currently building a permanent casino complex in River West after being selected for the project under former Mayor Lori Lightfoot. Bally's has recently opposed efforts to legalize video gambling in the city, a matter on which Mayor Johnson has been hesitant. In late October, Kelly established a campaign fund that has already raised over $450,000. While he has not formally announced his candidacy, he states he is assembling a team in preparation for a potential run. He has pledged to address potential conflicts by divesting from his lobbying firm, All-Circo, Inc., though the timing of such a move remains unclear.

  • In late October, Kelly established a campaign fund that has already raised over $450,000.
  • In 2025, Kelly lobbied both the mayor's office and city alderpeople on behalf of Bally's Corp., the operator of Chicago's first and only casino.

The players

John Kelly

A longtime lobbyist whose extensive client list presents potential conflicts of interest should he win office.

Brandon Johnson

The current mayor of Chicago, whose first term continues.

Jerry Reinsdorf

The owner of the Chicago White Sox, with whom Kelly has a business partnership.

Bally's Corp.

The operator of Chicago's first and only casino, for whom Kelly has lobbied.

William Singer

The chairman of Kelly's campaign fund, Citizens for John Kelly, and a former North Side alderman.

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What they’re saying

“I would not feel pressured to favor former clients, asserting that my guiding principle would be what is best for Chicago taxpayers.”

— John Kelly (newsy-today.com)

What’s next

If Kelly formally enters the mayoral race, his lobbying background is likely to be a central point of contention. His ability to navigate potential conflicts of interest will be closely scrutinized.

The takeaway

This case highlights the challenges of having a mayoral candidate with extensive lobbying ties and the need for transparency and accountability in local politics to ensure the public interest is prioritized over special interests.