At 93, political strategist Don Rose is old enough to remember the 1968 Democratic National Convention. In fact, he participated in the anti–Vietnam War demonstrations that famously accompanied it. He also recalls how Mayor Richard J. Daley’s reputation in the national Democratic Party never recovered after his police officers clubbed and gassed protesters. Chicago’s image, too, took a hit that tarnished it for years.

So Rose knows there’s much at stake for current mayor Brandon Johnson during this August’s DNC, particularly when it comes to handling the Gaza war protesters who are expected to show up in force. And the potential downsides far outweigh the upsides, Rose says: “I am not a believer that the conventions do that much for any particular city, unless something very bad happens. If it goes along without any significant problems, it’ll be fine, and [Johnson] will probably be credited. But certainly, if something goes wrong, he’s going to share in the blame. If he continues along his path now of not yielding any permits and having people march miles away from the event, that could lead to serious trouble because of the rebellion against that.”

Johnson may find himself torn between his antiestablishment roots and his current position as a member of the Democratic Party establishment. As a former union organizer, he’s a veteran of protest movements. To prevent clashes between law enforcement and demonstrators, his administration has promised to practice “constitutional policing,” respecting protesters’ rights but drawing the line at lawbreaking. That will likely be put to the test. Behind Enemy Lines, an outfit opposing Israel’s war in Gaza, has called to “Make 2024 as Great as 1968. Come to Chicago and Shut Down the DNC!”

The Secret Service is in charge of securing the convention, designated a “national special security event,” but Chicago police are responsible for areas outside the United Center. The city promises to set up Pollyannaishly dubbed First Amendment Zones for demonstrators in view of delegates. Expect protesters to challenge the rules. One coalition is vowing to march from Union Park to the United Center without a permit; however, the American Civil Liberties Union reached a deal with the city allowing abortion rights advocates to march down Michigan Avenue in view of delegates’ hotels.

“You have a man who has participated in First Amendment expressions and actions,” John Roberson, the city’s chief operating officer, says of the mayor. “He’s saying that anyone who wants to come to our city to engage in constitutionally protected expressions of their First Amendment rights will have the opportunity to do so safely. We are not going to allow things to devolve into aggressive, violent criminal behavior that results in the destruction of property or physical harm of people.”

What would happen then? During the 2020 social justice demonstrations, Chicago police dispersed crowds with pepper spray and called in the Illinois National Guard for backup. To avoid a repeat of those confrontations, police have been trained in de-escalation tactics and handling unruly protesters without resorting to arrests. Additionally, police superintendent Larry Snelling told representatives of Choose Chicago in May that the city will bring in 500 officers from around the state as reinforcements, but that Chicago officers will handle the area near the convention.

Johnson’s second challenge is to leverage the DNC to burnish the image of a city that, fairly or not, has a national reputation for violent crime. After Chicago was announced as the convention site in April 2023, a spokesman for the National Republican Congressional Committee snarked, “What’s the bigger concern: sirens drowning out nominating speeches or what items attendees must leave at home to make room for their bulletproof vest in their suitcase?”

In 1996, Mayor Richard M. Daley successfully used the DNC to soften memories of 1968 and to show delegates that “the old frontier town had become a world-class city, cosmopolitan in its architecture, renowned for its natural beauty, and secure in its commercial connections,” in the words of Inside the Wigwam: Chicago Presidential Conventions, 1860–1996, by R. Craig Sautter and Edward M. Burke. It was an era of domestic tranquility, so the younger Daley didn’t have to worry about clashes with demonstrators. That convention is best remembered for delegates dancing the Macarena and the installation of colorful wrought-iron fences with the Chicago star design overlooking the Dan Ryan.

Sautter, for one, hopes delegates will leave this convention talking about the “festive feel of the city” rather than its crime. “The only danger would be if some delegate was randomly shot, but the downtown will be so blanketed with security that’s unlikely,” he says. (Another worry: Republican governors will try to embarrass the city by increasing shipments of migrants that week.)

Organizers want the DNC to show off the entire city, not just downtown and the Near West Side. Last September, party officials in town for a convention preview had lunch at Bronzeville Winery. In February, Chicago Host Committee members toured Chinatown. During a May media walk-through, journalists from around the world were taken to Garfield Park Conservatory. Also that month, state party chairs ate at the Little Village restaurant Mi Tierra. “We looked at the ’96 convention and saw the efforts they made to incorporate local businesses, and we basically did that on steroids,” says Christy George, executive director of the Chicago Host Committee, which is working closely with the mayor’s office. Among the 12,000 convention volunteers will be “neighborhood ambassadors” from all 77 Chicago community areas and 23 suburbs, George says.

Minyon Moore, the D.C. political strategist and Chicago native who is chairing the DNC, says that showcasing the city’s diversity delivers a powerful message: “Conventions are a great backdrop for the world to see a city that is thriving. There are so many beautiful stories about Chicago that are written and not written. That, to me, is putting Chicago front and center of what the world really looks like, whether it’s Black, white, brown, Hispanic, Jew, Asian, whatever. Chicago is a reflection of a national convention.”

That’s the Chicago that Johnson wants to show off. His reputation depends on a watching world seeing unity and diversity, not conflict and chaos.