Mayor Brandon Johnson’s chief liaison to the Chicago City Council resigned Monday in an ill-timed move that signals more tough sailing ahead in already rocky waters.
After just 10 months as deputy mayor of intergovernmental affairs, Sydney Holman is leaving the Johnson administration after telling one City Council member she “doesn’t like the way she’s been treated” by top mayoral aides.
Holman could not be reached for comment.
She joined the Johnson administration in November 2023 after serving as deputy director of legislative affairs and House Liaison of Legislative Affairs for Gov. JB Pritzker and in a similar capacity for Cook County Board President Toni Preckwinkle.
Holman started her career as a research and appropriations analyst in the office of Mike Madigan, the now-indicted former speaker of the Illinois House of Representatives.
Her resume also includes a stint as a legislative strategist and policy advocate for Cozen O’Connor Public Strategies.
The timing of Holman’s resignation couldn’t be worse.
It comes as Johnson heads into what is certain to be a difficult budget season. Johnson has refused to rule out the property tax increase he campaigned against as he struggles to erase a $223 million shortfall this year and close a $982.4 million budget gap for 2025.
Johnson already has been forced to cast two tie-breaking votes. One, to spare his now-former Council floor leader from censure. The other, to pass a non-binding resolution demanding a ceasefire in the Israel-Hamas War in Gaza.
Emboldened by the defeat of Johnson’s signature “Bring Chicago Home” referendum, the Council then dealt the mayor an embarrassing setback on the gunshot detection technology contract known as “ShotSpotter.” The Council also has been without a permanent Zoning Committee chair for nearly a year because Johnson hasn’t secured the votes to confirm his choice: progressive firebrand Ald. Byron Sigcho-Lopez (25th).
“There is a lot of turmoil going on in city government right now. And a lot of good people are being forced out because they can’t deliver on this agenda that is driving this city into bankruptcy,” said Ald. Anthony Beale (9th), one of the mayor’s most outspoken critics.
“When you have good people like Sydney trying to carry a bucket with holes in it, you can’t deliver on that.”
“I’m hearing that there has been a consolidation of departments and that she disagreed with that consolidation,” in part, because it put Kennedy Bartley, former executive director of United Working Families, above her.
“Kennedy is a Socialist straight out of United Working Families and their agenda is the reason why this city has a $1.3 billion deficit. … This City Council is pushing back because they finally are seeing that aldermen need to step up and stop this city from going down the wrong path. We’re the ones who have to step up and save it,” Beale said.
“To put somebody who has no government experience in the lion’s den going into a budget season that’s going to be disastrous is a very bad move.”
Bartley could not be reached for comment.
She joined the Johnson administration last spring as managing deputy of external relations, a job created just for her. At the time, the Chicago Tribune quoted Bartley as saying her marching orders were to “make sure that we are executing the vision Chicago elected him to execute” and to give progressive groups and unions a direct pipeline to the mayor’s office.
Ald. Brian Hopkins (2nd) Johnson’s hand-picked Public Safety Committee chair, said when he talked to Holman earlier Monday, she mentioned the “stress of the job.” She didn’t tell Hopkins she was leaving, but he wasn’t exactly surprised.
“Sydney has the experience, the demeanor. She’s in it for the right reasons. She’s been fair. She’s been honest. She’s very hard-working. I talk to her on weekends — sometimes late at night. She’s very responsive. She brings a good skill set to the table. It’s a big loss,” Hopkins said.
“IGA is an inherently political position. Politics casts a long shadow over everything that office does. It’s inescapable. You need someone who has diplomacy skills, policy skills. And clearly, they need to be someone who has the trust of … the mayor. It’s not a job that anyone can just do.”
The mayor’s office had no immediate comment on Holman’s resignation.