Bill Daley on Democrats' prospects in 2024: "All of a sudden the cards have all been reshuffled"

Perhaps no city has been more connected with the Democratic Party than Chicago. And this week, Chicago will host its 12th Democratic convention, nominating Vice President Kamala Harris and her running mate, Governor Tim Walz.

We asked Bill Daley, who has spent his life in Democratic politics, about the new ticket. What case does Harris need to make to win this November? "I think she has to lay out a vision," Daley said. "She has to show who she is as a person, and kind of what she believes, not so much the litany of specific positions on issues, but sort of a sense of who she is and what does she believe in."

In 1968, at the height of the Vietnam War, the city hosted the Democratic convention. That year, like this year, the incumbent exited the race. And that year, like this year, violence marred the campaign.

At the turbulent convention that August, Bill Daley was at the side of his father, the late Mayor Richard J. Daley, the memory of whom still looms large in Chicago. Meanwhile, outside the convention hall, there were bloody confrontations between police and anti-war protesters, putting Mayor Daley in the spotlight.

Costa asked, "[Did] your father ever have any regrets years later about how that all played out in '68?"

"If he did, he didn't express them," Daley replied. "Look, he didn't like it. He didn't like what happened. You know, he didn't like the rap to Chicago. But you know what? He didn't look back."

• Remembering 1968: Chicago's bloody Democratic Convention ("Sunday Morning")

This week, there are planned protests of the Biden-Harris administration's handling of Israel's war with Hamas. "There'll be protests, there'll be a lot of protesters," Daley said. "I don't think they'll be out of hand. You know, it's not the '60s."

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The convention's key speaker on Monday night is President Biden. "I think there's gonna be enormous emotional reaction to the president's being there," Daley said. "I think that place will be rocking."

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Harris will accept the nomination on Thursday, setting the stage for a showdown with former President Donald Trump.

Daley said, "All of a sudden, the cards have all been reshuffled where he's the older guy and she's the young new generation. And that's a pretty powerful message, too, just that alone."

Many Democrats hope this crossroads will have echoes of another Chicago gathering, in 2008, when Barack Obama became the first Black American to win the White House. On Election Night, Obama told a crowd in Chicago's Grant Park , "It's been a long time coming, but tonight, because of what we did on this day, in this election, at this defining moment, change has come to America."

Daley (who served as Obama's White House chief of staff) said, "He was totally different from anybody who had ever run for president. Everything about his candidacy was change. He just exuded change, difference."

For Harris, there might be a balancing act; she is at once new to many Americans, but already in power as the incumbent vice president. "But, all due respect to vice presidents, they're really not known by the American people," Daley said. "The job itself kind of dictates you play second fiddle."

Costa asked, "Vice President Harris casting herself, it seems, like the change candidate – is that how you see it?"

"Absolutely. Just like Barack Obama did," Daley said. "The thought of the first woman being president is awfully exciting. I have three granddaughters. They're incredibly excited."

That excitement, Daley cautions, will soon be tested by the reality of a brutal campaign. "The Electoral College is very difficult for a Democrat," he said. "You almost have to pull an inside straight every time."

Costa asked, "A lot of Democrats are really giddy right now about the poll numbers, feel good about Vice President Harris. If you offered a word of caution to them, what would you say?"

"Ninety days is a long time," Daley replied. "Ninety days, in politics, is a lifetime."

Watch CBS News' live anchored coverage starting Monday, August 19 at 5:00 p.m. ET, streaming on CBS News 24/7, Paramount+ and Pluto TV, with primetime coverage from 8:00-11:00 p.m. ET on CBS.

Story produced by Mark Hudspeth. Editor: Joseph Frandino.

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• Thanks to Manny's Deli , Chicago