ABC7's Paul Meincke has a look back on some of what we think we've heard the mayor say over the years.
When Rich Daley was running for mayor 22 years ago, one of his opponents said the mayoralty was not something to be passed generation to generation like a family heirloom.
"I don't know what he's talking about. Nothing's a 'hairloom,'" Daley said.
Yes, over the years, there have been many malaprops and misspellings.
"That is state money -- underline that -- S-A-T-E money," Daley once said during a press conference.
As big city mayors go, he was far more accessible than most. He often talked all topics, sometimes, with considerable energy.
"He was asked once at the airport whether his brother would be running for governor and whether he welcomed that because of all the scrutiny," said WLS-AM political reporter Bill Cameron.
"Scrutiny? What else do you want? Do you want to take my shorts? Give me a break. How much scrutiny do I have? You go scrutinize yourself. I get 'scrootened' every day by each and every one of you. It doesn't bother me," said Daley.
The press was often his foil. He sometimes portrayed reporters as disconnected suburbanites, disconnected from reality.
"We don't want people to have guns. You can have all the guns you want in the suburban area. You can keep them all where you live," he told a group of reporters once/
Sometimes, he chose not to talk. Once when a reporter asked a question and asked the mayor cared to respond, Daley said":
Sometimes, he got angry.
And one time, the father cried when his then-teenaged son was involved in some drinking and a fight and a boy got hurt.
"I am more deeply disturbed for the young man who was injured in the fight," Daley said tearfully.
"Here again, this is a strength and not a weakness because he shows himself to be emotional like many people and just a regular guy," Cameron said.
The "regular guy" thought it was goofy when Disneyland got a no-fly zone and Chicago didn't.
"Now, think of that. Minnie and Mickey has it. I mean, I can't believe that," Daley said.
"It goes again to the gift the father had that he shares in the ability to say something people are gonna get right here," said WBBM-AM Political Editor Craig Dellimore said pointing to his heart. "I mean, they get it here, and also here [the head] because it's just so funny!"
"I've said, 'Cuckoo' once. I'll say it again, 'Cuckoo,'" the mayor said.
Daley may have used humor to deflect, but the humor and the unexpected is something the regular scrutinizers will miss.
"This is not a secret. Everybody knows this," Daley once said.