In August 1999, Barack Obama strolled amid the floats and bands making their way down Martin Luther King Drive on Chicago’s South Side. Billed as the largest African-American parade in the country, the summer rite was a draw over the years to boxing heroes like Muhammad Ali and jazz greats like Duke Ellington. It was also a must-stop for the city’s top politicians.
Back then, Mr. Obama, a state senator who was contemplating a run for Congress, was so little-known in the community’s black neighborhoods that it was hard to find more than a few dozen people to walk with him, recalled Al Kindle, one of his allies. Mr. Obama was trounced a year later in the Congressional race — branded as an aloof outsider more at home in the halls of Harvard than in the rough wards of Chicago politics.
But by 2006, Mr. Obama had remade his political fortunes. He was a freshman United States senator on the cusp of deciding to take on the formidable Hillary Rodham Clinton and embark on a long-shot White House run. When the parade wound its way through the South Side that summer, Mr. Obama was its grand marshal.
The secret of his transformation — which has brought him to the brink of claiming the Democratic presidential nomination — can be described as the politics of maximum unity: He moved from his leftist Hyde Park base to more centrist circles; he forged early alliances with the good-government reform crowd only to be later embraced by the city’s all-powerful Democratic bosses; he railed against pork-barrel politics but engaged in it when needed; and he empathized with the views of his Palestinian friends before adroitly courting the city’s politically potent Jewish community.
To broaden his appeal to African-Americans, Mr. Obama had to assiduously court older black leaders entrenched in Chicago’s ward politics before selling himself as a young, multicultural bridge to the wider political world.
“There are some people who say he’s not strong enough on this or that, that he’s wishy-washy, that he’s trying to have it both ways,” said Abner J. Mikva, a former congressman and mentor to Mr. Obama. “But he’s not looking for how to exclude the people who don’t agree with him. He’s looking for ways to make the tent as large as possible.”. . .