Heading into re-election, Chicago Mayor Rahm Emanuel made the tough decisions to strengthen Chicago’s schools, improve the safety of neighborhoods, and stabilize the city’s finances. It also created a tough re-election environment for Rahm, that national media called “the fight of his political life.” Public polling showed a tight, single-digit race. As part of the Chicago Forward Super PAC in support of Rahm Emanuel’s re-election, we developed innovative advertising that sought to drive the distinction between Rahm and his opponent -- particularly on the issue of property taxes. In “For Chicago,” we emphasized the tough, but necessary efforts Rahm led to improve Chicago’s finances and quality of life. In “Milton,” through the voice of a retired police officer, we put a spotlight on the opponent’s ill-advised plans to raise property taxes -- focusing on potential consequences affecting Chicago’s hard-working middle class.