This time around, Preckwinkle, 71, is not sitting another election out. She enters the runoff for mayor as a candidate of contrasts: both an entrenched political insider and a groundbreaker who would be the first African-American woman to lead Chicago.
Quiet and forceful, Preckwinkle has worked within the confines of party politics but has still managed to strike out as a leading progressive on issues such as criminal justice reform and affordable housing.
She has also been marred by scandal in recent months, damaged by her relationship with Ed Burke, an alderman who was charged last month with a federal crime, and her handling of sexual harassment allegations directed at her (now-fired) chief of staff.
Preckwinkle’s deep history in county politics — she has been chair of the Cook County Democratic Party for eight years — has opened her up to attacks from other candidates that she is the establishment and too quick to compromise. She says she is “uniquely qualified” to be the mayor of Chicago.
“Your job always, if you’re in office, is to try to move your agenda forward and get things done,” Preckwinkle told the Chicago Tribune. “You know, I’m not into being Don Quixote.”
Preckwinkle grew up in St. Paul, Minnesota, took an interest in politics as a teenager and attended college at the University of Chicago in Hyde Park, the liberal neighborhood on the South Side that would become her political base.
After teaching in both public and private schools, Preckwinkle was eventually elected alderman of the 4th Ward.
She has worked to reduce the jail population in Cook County and supported the decriminalization of possession of small amounts of marijuana. As president of the Cook County Board, she pushed through a penny-an-ounce soda tax, which prompted a fierce backlash from critics who said it would hurt the poor. The pop tax was repealed, a political embarrassment for Preckwinkle.
After declaring a run for mayor, Preckwinkle has garnered powerful union support with endorsements by the Chicago Teachers Union and the Service Employees International Union.
She has said that as mayor she would favor overhauling the juvenile justice system, addressing racial bias in policing, and strengthening laws restricting guns. She has also called for a halt to school closings and a focus on environmental health, prompted by the disclosure that thousands of Chicago homes have dangerous levels of lead in their water.
In her television ads, Preckwinkle has fought back against the perception that she is part of the fabled Chicago “machine” because of her long history in city government, trying to turn the image in her favor.
“She’s not from the machine, but she’s a boss,” the ad said. “Toni is ready to take on the old boys club from day one.”
This article originally appeared in The New York Times.