A major shakeup is underway on Mayor Brandon Johnson’s team that works to get the City Council and other elected officials to vote for his agenda, eliciting fresh concern over an exodus of key administration staffers from City Hall before what is sure to be a difficult push to craft and pass the 2025 city budget.
On Monday, Sydney Holman, the deputy mayor of intergovernmental affairs since last November, resigned while two staffers brought on during her tenure left, per sources with knowledge of the situation. The departures followed an internal announcement last week that Johnson intends to install Kennedy Bartley, a progressive community organizer who joined the mayor’s office in May, in a high-ranking position that would oversee Holman’s role, sources said.
Johnson spokeswoman Erin Connelly declined comment Tuesday. “We cannot comment on personnel at this time,” she said.
Bartley and Holman did not respond to requests for comment.
The sudden exits from the office involved in lobbying aldermen, Springfield and other government partners to back the mayor’s priorities could spell difficulty ahead for Johnson. His administration is in the throes of a trying budget season, with recent forecasts showing a nearly $1 billion budget gap in 2025 and a $223 million one at the end of the current year.
How Johnson plans to make up the shortfall — whether via crossing his mayoral campaign red line of raising property taxes, looking to other revenue ideas, resorting to one-time budget tricks like a tax-increment financing sweep, enacting layoffs or other belt-tightening measures — is to be seen. His budget director instituted a citywide hiring freeze Monday, one that includes rank-and-file police and firefighters and has already bristled some aldermen concerned with Chicago police staffing levels.
But regardless of what combination of solutions Johnson will deploy, he will need at least 26 out of the 50 aldermen to support him. The job of wrangling those votes falls to the intergovernmental affairs team, which under Johnson has seen an unusual number of close votes and defeats.
It was unclear who Holman’s permanent replacement would be. But sources said Bartley’s new role would include overseeing the IGA team, which will have its deputy director Erik Martinez, who was brought into City Hall from Johnson’s mayoral campaign, stay on.
Though the IGA office has faced unique dilemmas, the Monday news follows a larger trend of people leaving city government. Through the end of July, 83 employees have quit or been let go from the mayor’s office under Johnson, 21 of them this year.
Turnover is expected during a regime change at City Hall, as it is Johnson’s prerogative to bring workers who prioritize his progressive mission into his administration. However, the churn of administrative roles, including many brought on after he took office, suggests a deeper and ongoing large-scale departure.
Monday’s changes at IGA were met with mixed reactions from aldermen and City Hall insiders. Supporters of Holman lamented that someone with vast experience in lobbying is gone while Bartley, whose resume is centered on progressive organizing, will gain influence. Holman previously worked as an IGA liaison under Gov. J.B. Pritzker’s office, and the Johnson administration has a plethora of unfulfilled requests in Springfield. Meanwhile, Bartley was most recently executive director of United Working Families, a political organization closely aligned with the Chicago Teachers Union.
However, some within the progressive movement viewed the reshuffling as a promising sign that Johnson’s left-leaning agenda will remain a priority with Bartley in a more prominent role. That comes after Johnson’s first chief-of-staff, the politically centrist Rich Guidice, quit in the spring and was replaced by Cristina Pacione-Zayas, who came up from the Northwest Side’s progressive coalition.
Ald. Scott Waguespack, 32nd, said Holman brought critical experience doing similar work in Springfield. Following her departure, the mayor will lose “the ability to really communicate with the new City Council,” he said.
“I think it shows they can’t manage very well,” he said, adding that he believed Bartley might struggle to work with aldermen who don’t share her politics.
The IGA office’s first sign of turbulence took place before Johnson took office, when his transition team fired predecessor Lori Lightfoot’s appointee Beth Beatty only to swiftly rehire her. But many aldermen said they felt Beatty’s role as the mayor’s official lobbying arm was hobbled under Johnson.
Toward the end of Beatty’s tenure, a high-profile censure attempt of a Johnson ally had to be broken by the mayor’s tie-breaker vote, a rare phenomenon that would soon present itself again following Holman’s November hiring. In January, Johnson cast another tie-breaker during a resolution calling for a ceasefire in the Gaza war following what sources said was a chaotic effort to count votes, though perspectives vary on how empowered Holman was to take charge.
Then this May, Johnson faced remarkable defiance from City Council when aldermen voted to take control of the ShotSpotter gunshot detection system’s future out of Johnson’s hands. Historically, it has been rare to see aldermen buck the mayor, whose IGA team is tasked with ensuring unfavorable items don’t go to a vote. Some Johnson allies, however, contend more independence is a sign of a healthy democracy.
Beyond the upcoming 2025 budget, the Johnson administration will likely face other critical votes including another push on ShotSpotter, a vote on the long-vacant Zoning Committee chair and a push to broadly allow additional dwelling unit construction across the city. On the Zoning issue, Johnson’s plan to install ally Ald. Byron Sigcho-Lopez, 25th, is already facing mutiny from Ald. Felix Cardona, 31st, a political moderate who is mounting a challenge for the powerful post.
All of that spells a critical moment for the coalition that got Johnson elected to the 5th floor of City Hall but has faced steep growing pains once in charge.
Ald. Andre Vasquez, 40th, a progressive critic of the Johnson administration, summed up the internal strife in a Tuesday post on X: “We need a real and frank discussion amongst and regarding the progressive movement here in Chicago.”
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