James Cappleman, 46th Ward
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ENTERED OFFICE: Rookie, defeating Molly Phelan in a runoff after incumbent Helen Shiller opted not to run
PREVIOUS LIFE: Social worker, critic of affordable housing
HOW HE MADE THE RUNOFF: Convinced ward's many Shiller haters he was one of them
HOW HE WON THE RUNOFF: Convinced Shiller's dispirited supporters that he actually liked her
BIGGEST CHALLENGE: Find political identity and stick with it
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