Janny Scott, New York Times
The rise of Barack Obama includes one glaring episode of political miscalculation. Even friends told Mr. Obama it was a bad idea when he decided in 1999 to challenge an incumbent congressman and former Black Panther, Bobby L. Rush, whose stronghold on the South Side of Chicago was overwhelmingly black, Democratic and working class.
Mr. Obama was a 38-year-old state senator and University of Chicago lecturer, unknown in much of Mr. Rush’s Congressional district. He lived in its most rarefied neighborhood, Hyde Park. He was taking on a local legend, a former alderman and four-term incumbent who had given voters no obvious reason to displace him.