He is losing his seasoned Chief of Staff Rich Guidice.
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The longtime City Hall insider is leaving the administration after less than a year on the job.
Guidice has served the city in different roles for more than three decades.
This comes at the same time the mayor's progressive agenda took a hit at the ballot box, with the loss of the Bring Chicago Home referendum.
"I'm still here standing, and I will be punching back," Johnson said.
On Wednesday, a defiant mayor promised to continue the fight for unhoused Chicagoans.
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"You all know who I am; we are going to keep organizing," Johnson said.
Johnson did not mention working with the business or real estate groups that opposed the referendum. Instead, the mayor suggested the same people who voted against Bring Chicago Home may be supporters of former President Donald Trump.
"He really drew a line in the sand against what he perceives to be business interests in the city; that's not a good position for a mayor of a big city to be in," said David Greising, president of the Better Government Association.
Ald. Jeanette Taylor, of the 20th Ward, agrees. As a former community organizer who worked with Johnson as an activist, Taylor said once elected to office, it is about governing and listening to all sides.
"I had to realize: I couldn't work for government and hate government," Taylor said.
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Taylor said that means not just organizing like-minded people, but working with the opposition.
"It has to happen with all of us at the table; we're not at the space of, 'now we in charge, gotcha.' It can't be that," Taylor said.
Greising said former progressive Mayor Harold Washington understood the difference between being an organizer and an elected official.
"He was a progressive mayor with an emphasis on the fact the he was mayor of the city of Chicago," Greising said.
While the mayor said he will continue to fight, he was not specific on how he plans to raise money for the homelessness issue.