CHICAGO (CBS) — Mayor Richard M. Daley’s time in office is concluding, and the end of the era has many Chicagoans thinking about the past 22 years.

The mayor himself has discussed his legacy in a series of interviews. But CBS 2’s Jim Williams had a different conversation with Mayor Daley.

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Williams was his press secretary for five years in the 1990s, and they had some fascinating experiences behind the scenes, away from cameras and reporters.

He saw a boss who, in his effort to make the city better, was hard on his people. A few days ago, Williams and Daley talked about that.

Williams showed Mayor Daley a photo, taken two months after he started as press secretary.

“This sums up our relationship – you talking, me listening; teacher-pupil,” Williams said.

“That seems like yesterday, doesn’t it?” Daley said as he laughed.

Williams gets one question about his entire work experience – what was it like working for Mayor Daley? The mayor wondered what Williams’ answer was.

“I say it was exhilarating,” Williams told the mayor. “It changed my life in a way nothing professionally has, and it was tough, because you’re tough on your people.

“Yes, I am,” Daley said.

“I saw grown men leave your office shaken, having been taken to the woodshed,” Williams said.

“Right, because something happened,” Daley said.”You know, to me it’s all about helping people. If you can’t see the side of the city – the human side – many times people miss it, and what we have do in life is quickly help people as much as possible.”

“But did you ever say after having to really yell at someone — as you did – that, ‘Maybe I went too far with this person?’” Williams asked.

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“No,” Daley replied. “You know what would happen? The next day I’d talk to him or call him or something or see him at a meeting or something… (and) make a joke about it. You have to be strong in a position but you don’t take it personal.”

When Mayor Daley announced this past September that he was planning to retire, Williams got many phone calls.

“People asked, ‘Are you shocked?’” Williams said to Daley. “I said, ‘Absolutely stunned,’” because when people would ask me about your future, I’d say he’s going to die with his boots on.”

“There has to be a meaning why you have to be here. I’m just as passionate, just has committed, everything. But there just has to be something and I thought, ‘I didn’t have that.’”

When Williams and Daley rode around together, the mayor always had a legal pad in his lap.

“I still do,” Daley said. “I talked about some graffiti, abandoned buildings. some garbage on the West Side. I put it down and said, ‘Make sure they get those.’”

So on Monday afternoon when he’s suddenly not mayor anymore, what is Daley going to do?
“Well, I’m going to have a nice luncheon with my family, and then relax,” Daley said.

“But when you look out that window and you see something that should be done, what are you going to do, mayor?” Williams asked.

“I don’t know,” Daley said with a big laugh.

He will be staying busy.

“I have to be,” he said. “Otherwise – I’m not going to just sit there in a rocking chair.”

When Williams joined the mayor in 1992, he had been in office only 3 years.

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During one moment of frustration, he said, “I can’t believe my dad was here 21 years,” not thinking he would one day be mayor longer than his father was.