Pragmatic Politics, Forged on the South Side

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 advisers at the time. 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 ...
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