Illustration: Nicholas Little

In 2005, shortly after his election to the Senate, Barack Obama used the royalties from Dreams from My Father to buy a Georgian revival on Greenwood Avenue in Kenwood. He didn’t live there long, of course: He moved into the White House a little more than three years later.

“Oh, he’s not going to live there again,” one of his neighbors told me in 2015. An ex-president, with his retinue of Secret Service agents and gawking tourists? Too disruptive to densely populated Kenwood, she surmised.

It’s been pretty clear for a while that she was right. For one thing, the Obamas have said that they’ll stay in Washington, D.C., for at least two more years so daughter Sasha can graduate from Sidwell Friends School. Then they’re likely to move to New York City, where some reports have Obama teaching law at his alma mater, Columbia University. Like those of so many others who have used Chicago as a training ground for a career on the coasts, Obama’s ambitions have outgrown the city.

“I don’t know if it would be a comfortable fit here, because he’s such an outside figure,” says political commentator Laura Washington, a native South Sider who has followed Obama’s career since he was a state senator. “Chicago needs to be Chicago, and Barack Obama needs to be Barack Obama. He’s not a Chicago creature anymore. He’s a world figure.”

Obama never really was a Chicago creature, despite living here for 19 years (with a three-year break to go to Harvard Law School), marrying a local girl, and representing the South Side in the state Senate. Like his patron, Oprah Winfrey, and his basketball hero, Michael Jordan, who built careers here without going native, he was always more in Chicago than of Chicago. During his unsuccessful 2000 run for Congress, he described himself as “a salmon swimming upstream on the South Side,” explaining that as president of the Harvard Law Review, he could have clerked for the Supreme Court and then gotten rich on Wall Street, rather than jump into the city’s political fray.

Arriving here when Harold Washington was mayor, Obama was attracted by Chicago’s reputation as America’s capital of black political empowerment: It’s produced more black state officials, representatives, and senators than any other city. Obama built on the victories of Washington and Senator Carol Moseley Braun, which gave the black community confidence that it could lift one of its own to the highest office. As Al Kindle, a political strategist and an early Obama adviser, said in a postelection interview, “We were looking for someone to do it, and he was looking for a place to do it in.” That someone had to be an outsider. A traditional Chicago pol, tainted by the alliances and the dealmaking of the city’s shady political culture, could never succeed on a national stage.

So what is next for the soon-to-be-former president? Mark Updegrove, director of the Lyndon Baines Johnson Library and Museum in Austin, Texas, and author of Second Acts: Presidential Lives and Legacies After the White House, predicts Obama, a youthful 55 years old, will be an activist in the mold of Jimmy Carter and Bill Clinton—and he’ll need a bigger platform than Chicago. “This is a global figure, and New York is more of an international city,” says Updegrove. Obama has already announced that he plans to work for state-level redistricting reform, with the goal of electing more Democratic legislators, and he will continue to play a leadership role in My Brother’s Keeper, a national mentoring program he started in 2014 for African American boys. 

That said, former U.S. secretary of education Arne Duncan, who recently moved back to the South Side himself, thinks Obama will be in Chicago “a lot”: “This is where the [Obama] library is going to be. This is where his closest and most significant friends are.”

The city will still get plenty out of the relationship. Obama’s main connection will be his $1 billion presidential library, scheduled to open in 2021 on a sliver of Jackson Park between 60th and 63rd Streets. (No decision yet on whether he’ll have an apartment in it, as Bill Clinton does in his library.) Obama recently told a group of middle school students that he wants to go back to community organizing, the work that brought him here in the first place. While street-level activism is something else Obama has obviously outgrown, he can convene activists from around the country at the library, says Martin Nesbitt, the president’s best friend and chairman of the Obama Foundation. “We might equip those community leaders to bring change,” he says. “It’s an evolution of his early career. He’s gone from being a local community organizer to his current position as a global community organizer.”

Obama’s presidential library will be the first located in an urban neighborhood—Woodlawn, not far from where Obama started organizing in the 1980s. As a monument to a historic presidency, it’s going to bring jobs, tourists, hotels, and restaurants to the South Side. “This is a face-lift and a spiritual lift, not only for the South Side but for the Chicago area,” says U.S. Representative Robin Kelly, who served with Obama in the Illinois legislature and now represents Woodlawn in Congress. 

The library is what the South Side will have left of Obama. When Laura Washington tells her neighbors that their president isn’t coming home, they look crestfallen, but they understand: “He’s embraced and beloved more on the South Side of Chicago than anywhere else in the world. I think people will say whatever is good for Barack and Michelle is good with them.”

Obama drove from New York to Chicago 32 years ago in a $2,000 Honda. He’ll be going back there as an ex-president, perhaps forever leaving behind the city that made him—albeit with a $1 billion library as consolation prize.


The Boomerang Cabinet

Obama won’t likely be back, but many of his associates with Chicago roots have already returned.

Arne Duncan

The former U.S. secretary of education joined the social progress organization Emerson Collective last March and recently launched an employment program for young out-of-work black men.

Bill Daley

He succeeded Rahm Emanuel as chief of staff and, like Emanuel, eventually came back here. Daley heads U.S. operations for Argentiere Capital, a Swiss hedge fund.

David Axelrod

Besides offering near-nightly commentary on CNN during the 2016 election, the former senior adviser now directs the Institute of Politics at the University of Chicago.

Susan Sher

These days, Michelle Obama’s first chief of staff serves as senior adviser to the University of Chicago president, Robert Zimmer.

Desirée Rogers

The former White House social secretary is Johnson Publishing Company’s CEO. At least for now. The company sold its flagship magazines Ebony and Jet last June, leaving her future with the company uncertain.

Michael Strautmanis

Valerie Jarrett’s chief of staff now leads civic engagement efforts for the Obama Foundation, which is building the president’s library.

Austan Goolsbee

Obama’s former chairman of the Council of Economic Advisers teaches economics at the University of Chicago’s Booth School of Business.

Rahm Emanuel

Obama’s first chief of staff left office in 2011 and was never heard from again.