First, the father, Richard J. Daley ruled the city during great racial tension. Now, the son, Richard M. Daley, who has presided over a period of great growth and transformation. The battle is on for one of politics' most coveted jobs.
It is so famously a city of big shoulders and bare-knuckled politics. Think about what it feels like to get smacked in the mouth with someone's hand or fist. That's Chicago politics.
Why would Rahm Emanuel leave the White House to jump back into that fray? One political expert called it a Chicagoan's highest ambition, even better than being president.
The outgoing mayor kept a lid on the ethnic tensions that boiled over after his father's death. Daley also built world-class parks and lured global business.
"I love Chicago more than you can imagine," he said.
But he leaves behind dangerous streets and massive debt as Chicagoans brace for another round of the city's favorite contact sport.
But Daley's wife Maggie is also battling cancer and was in the hospital this week.
"She's doing well," Daley said. "We were at Washington. She was at Washington Georgetown Hospital, great care, came home, doing very well. First thing she asked me during the couple days is all about after-school programs, about helping teenagers. We have to do more, not only in Chicago, but around the country."
Daley said passion, commitment and a love for people are essential for a long political tenure.
"They'll disagree with you and yell and scream at you at the same time. You have to have the belief that you're not in for personal fortune," said Daley. "You have to passion and love the city. You cannot allow bureaucrats to get in your way. If you do, people don't understand it. They want a better way of life. And they want government to work with them, not against them."
Daley said he intends to leave office without leaving the city in debt.
"First of all, when you talk about debt, the federal government's in debt. They print money. And they go in debt. We have to balance our budget," Daley said. "When I leave office, this government's not going to be in debt. That's one thing we're not. We have to balance our budget. We have to make tough decisions. The federal government doesn't make tough decisions. They don't have to lay anybody off. They don't say, 'You have to cut here or cut there. The easiest job in the federal government would be budget director. Don't balance the budget. It would be great."
Daley said he has to cut police and fire and services to balance his budget.
"We have to live in reality. And what has happened in America is, people are not living a reality. And you can't just print money," he said.