During our 30 minutes, he revealed publicly for the first time that during the turbulent 1980's while state's attorney he had decided to quit elective politics. The mayor says it was a tragic turn of events that re-started his now historic political career.
"I've always told people I think the best job in America is always mayor," said Mayor Daley.
Daley told me before we began the tour of his inner office that there was a time when he thought he would never be mayor. By 1987, he says, he was a staunch supporter of the late Harold Washington.
"Truthfully, if he did not die in office, I was going to get out of politics," said Daley.
State's Attorney Daley won the 1989 special election to serve the remainder of Washington's term. Then, to heal the city's racial divisions, he says he bucked the national trend and supported minority set-aside programs.
"Even though the federal and state governments and a lot of cities walked away from that...we knew as a global city...you needed that type of ordinance," said Daley.
But in the meantime, some African American critics called the racial healing effort a "sham."
"The fact is that minority contracts or people working for the city, it's always one percent of some sort," said Cliff Kelly, WVON radio host.
Dozens of new police stations and libraries were built during the 20 years. But the Richard M. Daley decades will be remembered most for private sector development: new jobs and residential development particularly in the Loop and downtown.
"Business feels comfortable with Richard M. Daley or they would not make the investments that they have here in Chicago," said Ald. Ed Burke, City Council finance chairman.
"I never wanted to get a job that I had to retire in. That's not me," said Daley. "I never thought of getting the job to retire.
The mayor who has won six elections says he still keeps a political eye out for possible opponents.
"Everybody's vulnerable. No one's sitting up there so high that you're not vulnerable. I think that's a mistake. Then you lose your edge," said Daley.
But politics led to the convictions of his former aide, Robert Sorich, and Streets and Sanitation Commissioner Al Sanchez for giving city jobs to pro-Daley campaign workers. The mayor chided the feds for a double standard.
"So if you politically hire someone in the Justice Department, that's an ethical violation. But someone politically hired in the state or county or city, that's a federal violation of law. It's very interesting," said Daley.
At 67, the mayor's plate is fuller than ever. There's the recession and declining city revenues.
"I believe it's going to get worse. It's not going to get better," said Daley.
And there's the $15 billion O'Hare modernization program, successfully started but with an unclear financial plan to finish it.
In our interview, the mayor revealed a possible strategy for getting it done.
"I just sent a letter to President Obama, to the Congressional delegation all about, don't forget aviation," said Daley.
Mayor Daley is convinced that if the city wins the 2016 Olympics many infrastructure pieces, including O'Hare, could fall in place.
"Oh, they've helped tremendously. Are they going to help more? Oh sure. They've done that for everyone...summer and winter Olympics," said Daley.
The mayor called improving the city's public schools his greatest accomplishments. He bikes to stay in shape and said he was unaware of any political ambition on the part of his son Patrick.