"Very few secrets are ever kept, but that was one that was really important," Daley told ABC7.
Three months before he announced it to Chicago, Mayor Daley knew he was ready to call it quits.
"It was getting too easy maybe I should say. When you can really work things and get things done many times you need different challenges, and I thought, for me personally, I needed a new challenge," he said.
Some say he took the easy way out, leaving behind a projected $700 million budget deficit for next year and a city that had grown uneasy with his snap decisions -- from leasing the parking meters to tearing up Meigs Field under the guise of terrorism concerns.
"Are you finally ready to admit you carved those Xs into Meigs Field because you thought a park would be better?" ABC7's Ben Bradley ask the mayor. "Not me. I think our forefathers said that. I didn't say it. Our forefathers, Burnham and all those people who believed that open space belongs to the people of Chicago and not a few," he replied.
When it came to corruption - especially involving those close to him like patronage chief Robert Sorich - the mayor would denounce the crime but not the criminal. Leading some to speculate Chicago's hands-on mayor was happy to look the other way.
"Doesn't the mayor of Chicago need to be adamant about people who betray the public trust?" asked Bradley. "But you don't have to be kicking people. You don't have to kick people," said Daley.
Daley traveled the world, visiting 48 cities in 26 countries. The travel tab was often picked up by private organizations.
"If we're not a global city, we live in the past. You can take cities right now that have no global participation -- they're not going to be around," he said.
The mayor seems to be enjoying his farewell tour of the city that is synonymous with his name. But he also appears more than ready to say so long.
"You only have one mayor, only one person speaks on behalf of the city of Chicago, and that's Rahm Emanuel," said Daley. Any second thoughts about walking away? "No, none whatsoever."
Mayor Daley said he decided to keep his summer-time decision to retire secret until the fall announcement so as to not create a power vacuum where nothing got done. He also said after Monday the public will still see him around town speaking on issues important to him, but he won't be Monday morning quarterbacking Rahm Emanuel's decisions as mayor.