Cook County Board President Toni Preckwinkle, who announced her candidacy to replace Rahm Emanuel as Mayor of Chicago on Thursday, has a reputation as a smart politician who only goes for sure things. That could be a result of lessons learned: She ran for her first elected position — alderman of 4th Ward on the city’s South Side — three times, in 1983, 1987, and 1991, when she finally won. Even after winning in 1991, her victory was the subject of a court battle that lasted nearly until her reelection in 1995.

In her first term on the City Council, Preckwinkle earned a reputation as an “independent,” which in the Chicago political parlance of the time typically meant someone who at times opposed Mayor Richard M. Daley and supported process-oriented “good government” reforms.

Preckwinkle, a Minnesota native and former high school teacher, soon became involved with the Independent Voters of Illinois-Independent Precinct Organization (IVI-IPO), a mostly nonideological network of ward organizations that was borne of opposition to the Democratic Party machine. The IVI-IPO served different interests in different wards, but generally represented independence from City Hall, “good government,” and locally focused, “process-oriented” reform.

The 4th Ward, encompassing the professional liberal enclave of Hyde Park, anchored by the powerful University of Chicago (U of C), was a perfect base for a politician of Preckwinkle’s ilk. The professional-class liberals occupying the neighborhood responded to socially liberal policies coupled with the type of good-government posture that signals autonomy from machine politics. Hyde Park is also the neighborhood that elevated Barack Obama, of whom Preckwinkle was an important early backer when he ran for state senate in 1996.

Residents of Hyde Park also have tended to support developer-friendly candidates. Racially diverse but dominated by the U of C and upper-income professionals, the politicians who emerged from the neighborhood over the past twenty-five years — including Obama and Preckwinkle’s successor Will Burns, who would go on to work for Airbnb — were less polarizing, particularly around issues of class and race, than aldermen from the predominantly black South Side wards that surround it.

For twenty years, Preckwinkle was considered independent of Mayor Richard M. Daley, occasionally voting against his budgets and his appointees. She had the distinction of being part of a group that received the first of Daley’s soon-to-be-legendary City Council floor temper tantrums in 1993 when she voted against James Joyce’s appointment as Fire Department commissioner due in part to Joyce’s long tenure in the Department at a time when it was notoriously bereft of nonwhite firefighters. At the same time, during her term in that office, she oversaw significant gentrification of the ward and the expansion of U of C housing and commercial developments into working-class black neighborhoods surrounding Hyde Park.

Preckwinkle can come off as a traditional technocratic Chicago politician: Determined to work within the system without provoking the most powerful vested interests that pervade urban politics — big developers, big finance, well-endowed private universities, trade associations, and the status quo that keeps those forces dominant in the city.

Preckwinkle has accepted significant money from real estate developers over the course of her political career and has ties to the U of C and the constellation of property owners and developers around it. During her time as alderman, Preckwinkle’s view of development has been to stabilize neighborhoods by enticing the type of commercial and residential development that would lure in higher-income people. However, this development has also been known to lead to displacement for working-class families of color at the peripheries of Hyde Park.

In 2010, when she challenged incumbent Cook County Board President Todd Stroger, Preckwinkle was subjected to some vicious attacks characterizing her as an “Aunt Jemamie,” in thrall to “Massa Daley,” implying she was little more than a “palatable” black politician sponsored by white middle-class voters and financial interests. This line of attack has not been uncommon in her career, but Preckwinkle won that primary handily.

At the time, Preckwinkle said she decided to challenge Stroger because of his inattention to juvenile-detention reform — an issue she had been appointed to review and reform. That campaign — a big leap from her previous position of alderman to managing a $3 billion budget — was hatched in some reportedly suspicious circumstances, with questions being raised that Preckwinkle may have cut a deal with then-Mayor Daley to support (or not oppose) her bid for the presidency in exchange for her support for (or non-opposition to) Daley’s plan to host the 2016 Olympics. At the time Preckwinkle’s close relationship to developers, including accused slumlord Rev. Dr Leon Finney, came under close scrutiny.

The criticism of Preckwinkle as a purely technocratic politician, however, is complicated by the fact that her “work from the inside” strategy has also borne occasional fruit in achieving progressive priorities. Upon assuming the presidency of the Cook County Board, Preckwinkle took action to reform the county jail system, giving her office authority to release low-risk defendants awaiting trial. Jails sit “at the intersection of race and poverty,” Preckwinkle commented at the time.

Preckwinkle took on criminal justice reform in her campaign policy document, the “Compact for Change,” expressing support for decriminalizing marijuana to reduce the jail population. She went on to support the insurgent campaign of Kim Foxx, who took on and defeated incumbent State’s Attorney Anita Alvarez. Alvarez had become a high-profile target of local activists after footage of the killing of teenager Laquan McDonald by Chicago Police officer Jason Van Dyke became public. Foxx has implemented a number of reforms including around the issues of cash bond and reducing incarceration.

Over the course of her tenure, Preckwinkle has had a measurable impact on criminal justice reform: The Cook County jail population has declined by 15 percent since she took office. On health care, Preckwinkle used the expansion of Medicaid provisions under the Affordable Care Act to create CountyCare, which enrolled some four-hundred thousand people. In addition to reducing the number of uninsured residents using county health services, that expansion allowed the county to save on local health care spending. The hospital system, like the court system, has been a frequent area of proposed cutbacks by Preckwinkle, bringing her into conflict with public-sector unions which regularly have had to push back.

Preckwinkle also publicly challenged Mayor Rahm Emanuel’s 2013 decision to close more than fifty Chicago public schools, suggesting that it may have been a deliberate effort to weaken the public school system and contrasting the closure of schools with the explosion of the jail population. Preckwinkle spotlighted that the school closings were going to happen almost entirely in black neighborhoods, calling that “problematic” and asking if the closures weren’t just a deliberate attack on public schools.

Preckwinkle’s independence is more a mindset than a substantive political ideology. In 2010, she also ran on a promise to repeal a sales-tax increase passed by her predecessor — a promise she was forced to renege on when a plan she supported a cut public workers’ pensions failed in Springfield — a sign of her independence from labor unions who were among her top campaign donors.

To close a budget gap and avoid layoffs, in 2017 she helped push through a tax on soda (or “pop” if you’re local). When trade associations and retailers instigated a backlash, the tax was repealed, and Cook County ended up laying off hundreds of county employees, including public defenders — layoffs she called “heartbreaking.”

Preckwinkle also declined to endorse Jesus “Chuy” Garcia — her County Board ally and floor leader — in his near-miss progressive challenge to Mayor Rahm Emanuel in 2015. If Preckwinkle had come out in support of Garcia, it could have potentially had an impact on the election, helping him win over “good government” liberals and countering Emanuel’s characterization of Garcia as unschooled and undisciplined in matters of budget management. Instead, Emanuel went on to win in a runoff.

Preckwinkle likes a sure thing, and she wouldn’t be running for mayor if she didn’t have reason to believe she could win. Her entire career has been characterized by independence — but independence from whom? As the most powerful politician in the county, Preckwinkle’s independence could just as easily be seen as an ability to resist pressure, whether from above or below.

Her sensible approach to governance is more limited by political imagination than by ideology. In her run for mayor, her willingness to address issues such as racist criminal justice practices and service disparities between the rich and the poor will likely continue to be bound by her understanding of what is both possible and reasonable given the powerful forces around her.

Many commentators have predicted that Preckwinkle may quickly become one of the front-runners in a mayoral race that already features over a dozen candidates. If she does, the challenge facing organizers in Chicago will be to push her to reject the same policies of austerity and embrace real progressive revenue solutions: financial transaction and corporate head taxes, infrastructural improvements and investments in public services that can keep working-class families in the city.

It also means being prepared to exert pressure and demonstrate power around issues ranging from policing to education to housing that stand in opposition to the powers that have dominated City Hall for decades.