Barack Obama’s path from Hyde Park state senator to two-term president moved through a series of defining moments that political insiders say are unlikely to be repeated.
Few journalists tracked that rise more closely than Lynn Sweet, former Washington bureau chief for the Chicago Sun-Times, who first encountered Obama in 1999 when he stopped by her office at the National Press Building.
“He wanted to get to know the Washington scene a little more, so he came and visited me in my office at the National Press Building,” Sweet said.
At the time, Obama was three years into representing Hyde Park and Englewood in the Illinois state Senate and was already looking toward a larger stage. His first attempt came when he challenged longtime South Side congressman Bobby Rush — a campaign Sweet described as “very ill-fated.”
“He couldn’t really make his case for ousting Bobby Rush, who was a beloved figure in the South Side community,” she said.
It would be the only losing campaign of his career.
The turning point came in July 2004, when Obama delivered the keynote address at the Democratic National Convention in Boston.
“To say he knocked it out of the box isn’t a big enough superlative,” Sweet said.
The speech — remembered for the line “No Red America, Blue America … United States of America” — set the stage for his 2004 U.S. Senate run. When Republican opponent Jack Ryan exited the race, Obama faced non-Illinoisan Alan Keyes in the general election and won decisively.
Around the same time, Obama was quietly laying the groundwork for something larger. His 2006 book, “The Audacity of Hope,” became the vehicle.
“He went on a book tour across the nation. He drew massive crowds, and it was a test run of how you put together a campaign,” Sweet said. “It also laid a lot of groundwork for meeting people who could be useful in fundraising and making a lot of contacts.”
His campaign team took shape during that period, including fellow Chicagoans David Axelrod and Valerie Jarrett. In the 2008 Democratic primary against Hillary Clinton, Obama’s limited legislative record worked in his favor.
“Not having a record is a plus, because people cannot use your votes against you,” Sweet said.
In the general election, he faced Republican John McCain, a war hero whom Sweet described as “a very worthy adversary” who “did not have a good campaign.”
Obama secured twice the electoral votes as McCain. Four years later, he defeated Mitt Romney by a similarly wide margin.
The movement that began on Chicago’s South Side will now be permanently memorialized there. But Sweet said what Obama built is not something that can simply be studied and reproduced.
“He was able to create this movement, this ‘Yes We Can’ movement back in 2008 that was unrivaled in its time and has never been matched or duplicated since,” she said.