CHICAGO When Rahm Emanuel resigned as President Barack Obama's chief White House enforcer two years ago, many Washington pundits wondered why he abandoned a place at the pinnacle of power to try to govern one of America's most unruly cities.
Now as Chicago's mayor, Emanuel is confronting nearly 30,000 angry striking teachers, 350,000 children out of school as of Monday and parents scrambling for caregivers or forced to miss work to stay home with their kids.
No stranger to the toughest decisions as Obama's White House chief of staff, Emanuel is discovering just how intractable are the problems of America's third largest city.
Behind the gleaming office towers and green space along Lake Michigan, Chicago is riven with poor performing schools, corruption, gang-related violence and urban poverty.
And the financial situation of both the school district and the state of Illinois is grim.
The famously aggressive Emanuel, who sometimes uses the "F" word to make his point, has found Chicago opponents willing to hit back just as hard.
"He is a liar and a bully," Karen Lewis, the Chicago Teachers Union president who called the strike, said of Emanuel at a Labor Day rally of thousands of teachers and supporters.
Emanuel has so far kept his cool in public, saying at a press conference late on Sunday that the two sides were close to an agreement.
"It is a strike that is unnecessary. ... Our kids do not deserve this," Emanuel said.
As recently as May, Emanuel was basking in the success of the NATO military alliance summit in Chicago, where he set the stage for Obama to play international statesman to some 60 world leaders.
Despite fears of violence from demonstrators opposed to the war in Afghanistan and economic inequality, Emanuel's police force kept the peace with restraint.
That success helped Chicago put behind it the stain of the 1968 Democratic convention, when Chicago police attacked anti-Vietnam war protestors in bloody street battles.
Emanuel has faced a summer of discontent since NATO, as the city made national headlines with a surge in its murder rate because of gang violence, and the face-off with teachers.
At one point in the spring, the number of murders in Chicago was 50 percent higher than a year ago and some children going to school were killed in gang crossfire. It has been routine for more than a dozen people to be injured or killed by gun violence in a single weekend this summer.
Emanuel has argued that the violence is confined to a few neighborhoods of the city and that crime overall is down 10 percent from a year ago.
Emanuel, 52, won the Chicago mayor's race on February 22, 2011 with 55 percent of the vote in a messy six-way race and took office in May of last year.
The timing of the teachers' strike is uncomfortable for his national political ambitions. Many people in Chicago assume Emanuel is in a hurry for change because he has bigger plans, including a possible run for U.S. president in the future.
He spoke in support of Obama at the Democratic National Convention last week and has taken on a fundraising role for the president in the final weeks of the election campaign.
Chicago has had its share of mayors with big personalities, including the legendary Richard J. Daley, his son Richard M. Daley and the city's first black mayor, Harold Washington.
Emanuel relishes the spotlight, and around the country unions, politicians and education reformers will be watching how he resolves the strike. It is the biggest public or private labor action in the country in a year and the first teachers strike in a major U.S. city since 2006 in Detroit.
But a nasty confrontation in Obama's hometown between a Democratic mayor and organized labor could sour relations with unions just weeks before the November election. Democrats rely on unions for funding and help in getting out the vote.
Adding to the strain on relations between Democrats and unions, the fight in Chicago is over reforms backed by Obama's Education Secretary Arne Duncan through the so-called Race to the Top initiative.
"The policies pushed by Rahm Emanuel, which are being simultaneously implemented in New York and many other cities ... (are) trying to weaken tenure and introduce merit pay," said Mark Naison, a professor at Fordham University and education activist. "The union is saying enough is enough."