Chicago Mayor Rahm Emanuel promised bold measures to help fix the nation's worst-funded pension systems and failing schools, stabilize city finances and combat violence when he was elected to lead the nation's third-largest city in 2011.
But despite some successes — including attracting new companies and raising the city's minimum wage — many of the long-standing problems that Emanuel inherited will remain when he leaves office early next year. Emanuel announced Tuesday he will not run for a third term.
Here is a closer look at some of the biggest challenges faced by Emanuel — and his successor:
Chicago's four pension systems are about $28 billion short of promised benefits, prompting Emanuel's financial team to consider a risky fix: borrowing more than $10 billion by issuing bonds to help lower that debt. The idea is that the pension funds would invest the proceeds and hope that the returns would be greater than the interest the city would have to pay on the bond debt.
But experts say pension obligations bonds are risky because investments could fail or the stock market could falter. City officials say they're just evaluating the idea, but it underscores the financial straits the city finds itself in.
Emanuel has sought to fix the problems, raising the amount that Chicago pays into the pensions every year — though still far short of what is owed.
The city has increased taxes by more than $820 million since 2015 to boost contributions to the pension funds.
Chicago's violent crime has drawn national attention — including criticism from President Donald Trump and Attorney General Jeff Sessions — with the number of shootings and homicides climbing to levels not seen in nearly two decades and exceeding the bloodshed of any other U.S. city. The number of slayings in each of the last two years was more than twice the total of Los Angeles and New York combined.
The number of homicides had fallen to 415 in 2015 — the lowest level in a half-century — before jumping to 771 in 2016 and 650 in 2017.
Emanuel's administration ran up tens of millions of dollars in overtime to police to flood high-crime areas with officers, and the Chicago Police Department is hiring more officers, adding more than 1,100 in 2017 as part of a two-year hiring plan.
Prosecutors and police say they'll step up use of the state's anti-racketeering law to prosecute gang leaders. But even so, gang violence continues to plague the city's most dangerous neighborhoods.
Emanuel's announcement that he would not seek re-election came one day before the start of the first phase of jury selection for a white police officer's murder trial for the 2014 death of a black teenager.
Officer Jason Van Dyke shot Laquan McDonald 16 times, and a video later released by the department showed he was holding a small folding knife and veering away from officers. That led to protests and a federal investigation that found systemic failures in the Police Department accountability and training, deep-rooted civil rights violations by police including racial bias and a tendency to use excessive force.
The city has agreed to far-reaching reforms of the police under strict federal court supervision, abandoning a draft deal on reforms with the Trump administration that envisioned no court role. The oversight will include an independent court-appointed monitor.
One of those running for mayor is Garry McCarthy, a former New York police leader whom Emanuel hired to stem violence but who was fired after the McDonald shooting.
Emanuel, who inherited a school district facing a $700 million budget shortfall, got off to a rocky start with teachers, canceling 4 percent raises and asking for concessions that led to a strike in 2012, the first walkout in Chicago in 25 years. He also angered parents by closing more than 50 schools at once in 2013.
Emanuel successfully implemented a longer school day, and the five-year graduation rate has ticked up to 78 percent under Emanuel — though the number is less than 65 percent for black males.
But leadership of the district has been plagued by scandals.
Former CEO Barbara Byrd-Bennett, whom Emanuel first chose to lead the struggling district, was sentenced to 4 1/2 years in prison in 2017 for a scheme to collect hundreds of thousands of dollars in kickbacks in return for steering $23 million in no-bid contracts to an education consulting firm where she had once worked.
Later that year, the next CEO, Forrest Claypool, resigned after being accused by the Chicago Board of Education's inspector general of repeatedly lying in a "full-blown cover-up" during an ethics investigation involving the school district's general counsel. Ronald Marmer was receiving $200,000 a year in severance payments from his old law firm, while supervising that firm's work for the Board of Education in violation of ethics rules. Claypool was accused of lying about whether he had sought changes to a bill that was part of evidence collected in the investigation.