Chicago Mayor Rahm Emanuel will leave behind a mixed legacy after he announced this will be his final term as mayor of the Windy City.
Emanuel, who revealed Tuesday he would not seek re-election, can point to significant changes in the city he has guided for the last seven and a half years, but there remain many challenges that could have cast doubt on a re-election bid.
In his bombshell press conference Tuesday morning, Emanuel touted the changes he orchestrated in Chicago Public Schools.
Among the arguable positives are longer school days, a full day of pre-K, and revamped community colleges.
Still, he faced criticism from many education advocates over controversial school closings - and the potential for even more. Scandals plagued his appointed school board, particularly as former CPS CEO Barbara Byrd-Bennett was sentenced to four years for bribery.
But Emanuel's announcement comes at a pivotal time for the city with just one day before the start of the one of the biggest police shooting trials Chicago has faced -- the murder trial for Officer Jason Van Dyke, who has been charged in the 2014 shooting of Laquan McDonald and pleaded not guilty.
The release of dashcam video one year after the shooting, and only a few months after the mayor won re-election, thrust the city into a national spotlight.
The Emanuel administration was compelled by a court order to release the dashcam video, which showed the white officer shooting the black teen 16 times as he appeared to walk away. His office came under scrutiny and some questioned whether politics played a role in the timing of the release. It also sparked a U.S. Department of Justice investigation into the Chicago Police Department's handling of the case.
Though murders and shootings are down from last year, the city has yet to shake its national reputation for violence. Last month, the city once again made headlines across the country after 12 people were killed and 70 others shot in a single weekend.
Emanuel long contended he inherited economic problems the city has long faced. He consistently said there were problems he took over from past administrations, including Richard Daley.
Emanuel contended he was forced to push for property tax increases, and a litany of fee increases to balance budgets. But, the city still has to account for a $28 billion pension shortfall.
But there's no denying the changes that were made to the city under Emanuel's leadership. Changes that are evident to those walking down the Riverwalk, using bike lanes or grocery shopping in areas that were once food deserts.
But there remains two Chicagos. One that thrives and another with inherent problems - problems that must be tackled by the city's 47th mayor.