James Cappleman, 46th Ward 

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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