Before Farewell Speech, Chicagoans Reflect On President Obama's Legacy

President Obama's adopted hometown of Chicago is often the stage for pivotal moments in his career. He claimed victory in Chicago in 2008 and again in 2012. And it's where he will give his farewell address on Tuesday night.

Many Chicagoans use the word "pride" when talking about Barack Obama. You can hear it in their voices. In this city, where President-elect Donald Trump got only 12 percent of the vote, admiration for President Obama is strong.

Kim Chisholm stood with thousands of others in the bitter cold this weekend to get a ticket to Obama's speech.

"I'm so excited," she says. "History in the making. I never made it to the White House, but I will see him here in Chicago."

Chicago officials say there are pluses and minuses to having such close ties to the Obama administration. On Monday, the city won a federal grant for nearly $1 billion to upgrade a major portion of the city's elevated commuter rail line.

Mayor Rahm Emanuel, Obama's first White House chief of staff, worked to make sure the funding came through before the administration changed hands.

"This will over the next four years create 6,000 jobs in the city of Chicago," he says.

Illinois' senior U.S. senator, Dick Durbin, says the city has been able to make significant infrastructure improvements with the help of federal funds, including high-speed rail and upgrades to O'Hare International Airport.

"Time and again, the Obama administration has not forgotten where he came from," Durbin says. "[He] has not forgotten the city of Chicago."

That's in part because the administration included a bevy of Chicagoans as Cabinet members and advisers, such as former Education Secretary Arne Duncan, advisers Valerie Jarrett and David Axelrod, and Commerce Secretary Penny Pritzker.

Tuesday night's speech and talk about an Obama legacy in Chicago are much more personal for some. Jacky Grimshaw worked in Chicago government under Harold Washington, the city's first black mayor, and was Obama's next-door neighbor for years. She says the country's first black president faced the same sort of opposition that Washington did and both men prevailed.

"And he put through the stimulus package that allowed communities across the country to deal with infrastructure projects that needed to get done," Grimshaw says of Obama.

Some community organizers take a more nuanced stance. Jitu Brown of the Institute for Educational Leadership says that while the president conducts himself with grace, he disagrees with many of his administration's education policies.

"And I think the disappointment is in a president who started as a community organizer. I would have really hoped there would have been space to really listen to the voices of the people directly impacted," Brown says.

At Valois Restaurant, not far from the president's Chicago home, customers can order a variety of Obama specials on the menu. Kimberly Barnes Staples was eating breakfast with her husband.

"For Chicago, specifically, he gave us a national profile," she says. "He showcased who we are as Chicagoans. He made us proud."

And Devi Austin, a retiree, says she personally benefited from policies Obama advanced.

"Because of the laws that he put in place for people who had just bought homes and was underwater, I got forgiven — forgiven, not modified — forgiven $60,000," she says. "I will miss President Obama."

While some Chicagoans express disappointment that the president didn't provide more help to deal with gun violence and gangs, others give him a pass, saying that's a problem for the mayor, not the president. So as Obama says farewell, Patty McNamara, a museum consultant, says she will be watching wistfully.

"It's kind of bittersweet," she says. "It's going to be a tough transition, I'm afraid."

There will be a tangible Obama legacy for Chicagoans, though. His presidential library and foundation will be built on Chicago's South Side. That means that even if the Obamas don't return there to live, the president will remain engaged in the city that gave him his political start.

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