Chicago Mayor Rahm Emanuel speaks Tuesday during a news conference at Tarkington School of Excellence in Chicago as the school’s principal, Vincent Iturralde, listens. (M. Spencer Green/AP)

Rahm Emanuel is not big on ambiguity. He was thrilled, a few days before he took office last year, when the Illinois House voted 112 to 1 for a school improvement package that, among other things, made it harder for teachers unions to call strikes.

A “historic day of opportunity for kids in the city of Chicago,” he said after the vote. Rank-and-file teachers were less pleased, particularly when an Emanuel ally boasted, “The unions cannot strike in Chicago.”

Teachers are now on strike in Chicago— loudly and enthusiastically — and Emanuel (D) finds himself in a far more pointed and public battle than he had bargained for. Under a national spotlight, his famous dealmaking skills are being severely tested by an increasingly familiar set of schoolhouse issues seen in communities across the country as contentious and often personal.

If the strike persists, its tone and outcome could ripple well beyond Chicago, given Emanuel’s close association with President Obama. Union support is important to the Obama campaign, which has been careful not to weigh in, even as Republican presidential nominee Mitt Romney swiftly spoke out against the Chicago teachers.

As thousands of teachers took to the streets again Wednesday, there was general agreement that the sudden strike had roots in the combative positions Emanuel took when he left the White House last year to run for mayor. His support of the Illinois law requiring a 75 percent union vote for a strike — up from 50 percent — was Exhibit A.

“It stuck in my craw,” said Xian Barrett, former political director of the striking Chicago Teachers Union and now a history teacher at a South Side high school. “It made me feel as though he had no respect for us as people.”

Karen Lewis, the blunt-spoken CTU president, put it another way last week, shortly before the union called a strike for the first time in 25 years: “The only way to beat a bully,” Lewis said, “is to stand up to a bully.”

When Emanuel won the job without a runoff after leaving his post as Obama’s chief of staff, it was clear that he was never going to be a warm and fuzzy mayor, not in the country’s third-largest city, the windy one with the outsize reputation for rough politics. Vowing to make Chicago work, he cruises for bruises, with a smile.

Some hits, some misses

Reviews have been largely positive, at least until the strike dominated the news and left parents of school-age children scrambling.

“When people say, ‘How long has the city council been so corrupt?’ I say, ‘Since 1837, the year the city was started,’ ” said Martin Oberman, a council member most recently in the 1980s. “Rahm came and cut through all that. He gets criticized for being tough and autocratic, and he’s probably more autocratic than he needs to be. But this is a very tough place. You can’t be a milquetoast.”

Longtime Democratic political consultant Don Rose thinks that Emanuel blundered with the teachers and has fallen short in addressing the city’s startling spike in violence. But he calls him “a breath of fresh air” on structural reforms, from combining government operations amid a $665 million budget deficit to redesigning garbage collection, an almost comical bastion of patronage.

The schools are another matter. The very attributes that allow Emanuel to cut through the clutter on some issues have hardened opposition to proposals that would change the way teachers are paid, retained and, if laid off, rehired. The mayor, who is lengthening the school day and plans to consolidate schools, is putting significant faith in charter schools and testing, two of the union’s biggest bugbears.

Just as Emanuel has described the strike as “avoidable,” critics of his approach to schools and teachers have said the same about his tactics. One former Chicago politician said backing the 75 percent rule was “like waving a red flag in front of the union.” He said labor relations demand a different skill set: “You don’t go around mandating things, or you’re asking for trouble.”

Former Chicago city council member Dick Simpson said wryly of Emanuel: “He accomplished a major feat: He got 90 percent of the teachers to rally around and vote for a strike. What he’s managed to do is convince the teachers, to use the language of the kids, that he’s dissed them.”

Emanuel has carefully honed his image as an egg-breaker, yet in Washington — where he was an indefatigable House leader and White House chief of staff in two administrations — he was also known as a tactician determined above all to put points on the board. Critics on the left, in fact, often hammered him for being too ready to cut a deal.

In Chicago, too, Emanuel has shown flexibility. Simpson said the mayor has mostly gotten his way with the 50-member city council since taking office in May 2011. At times the council pushed back, he said, and Emanuel “made a compromise that solved the problem.”

Calling this Emanuel’s “first major crisis,” Simpson said the dispute should be “relatively easy to resolve if they can get the egos out of the way.” By egos, he means those of the protagonists, Emanuel and Lewis, a tart-tongued former chemistry teacher who once aspired to be a stand-up comedian.

“He does not take kindly to being stood up to in the way Karen Lewis has stood up to him. You just don’t do that to Rahm,” Rose said, repeating the story told by Lewis that the famously profane mayor dropped an F-bomb during a contentious meeting. Emanuel countered that whatever happened, their meeting ended in a hug.

The strike has divided the city. An early Chicago Sun-Times poll published Wednesday showed that 47 percent of registered voters support the strike and 39 percent oppose it. In all, just 19 percent said Emanuel is doing a good or excellent job in handling the strike, which has kept the city’s 350,000 public schoolchildren home since Monday.

Support for strike

As negotiations continue, many teachers seem to be drawing sustenance from their own numbers, the support of students and parents, and the staccato honks of endorsement from passing cars. Barrett, the South Side history teacher, called Wednesday a “crazy, insane, happy day.”

Earlier in the week, one striking teacher carried a picket sign that said: “Emanuel is a bully. Stop Rahmunism!”

Another carried a sign that referred to the mayor’s decision to send his children to the private University of Chicago Laboratory Schools: “Fighting to Make CPS a district where Rahm would send his kids.”

Amisha Patel, who directs the Grassroots Collaborative, a community labor coalition, contends that Emanuel made a significant miscalculation.

“The man thought he could just bulldoze through his agenda, that the union didn’t have enough strength to fight back and that the public wouldn’t be behind the union,” Patel said as she organized a protest march for Thursday. “Folks get that this isn’t about bread-and-butter issues, that this is about the soul of public education.”

The strike has been underway for three days. Now what?

“The outcome is now impossible to predict,” said Terry Mazany, who served eight months as interim schools chief, ending when Emanuel recruited Jean-Claude Brizard from Rochester, N.Y., to run the nation’s third-largest school district.

“My concern is that it’s already gotten personal. It’s hardening the positions on each side,” said Mazany, who says that the longer the impasse endures, the harder it will be to recover. “To me, reform requires collaboration. You can’t mandate excellence.”