For the next 40 minutes, Emanuel delivered a "genuine" and "heartfelt" speech about police brutality and city violence that seemed "real," said critics and supporters alike who heard it, according to the Chicago Tribune.
But the reaction on the street was a very different story. Emanuel cried "crocodile tears," one protester said. The only people who believe it will be his "lap-dog city council," another said, according to the Tribune. They carried signs calling on Emanuel and his leadership team to resign.
And more and more — despite his speech Wednesday— it appears resigning could indeed be what Emanuel will be forced to do in order to restore Chicagoans' faith in their government. (Already, an Illinois state lawmaker is starting the process to recall him.)
Thanks in part to a series of missteps by the mayor after the shooting, exacerbated by a longer-term failure to address more systemic problems with Chicago's police department, Emanuel appears to have lost much of the city's trust. His approval rating has hit a record low of 18 percent, and 51 percent of residents think he should resign, according to a new poll from the Illinois Observer.
For Emanuel, trust is the most critical element right now for him to take any meaningful action to help a wounded Chicago. And it's increasingly difficult to envision a scenario in which whatever Emanuel does isn't viewed as a political Hail Mary to save his career by understandably frustrated and suspicious Chicago residents.
President Obama's former chief of staff has a reputation for being a savvy political operator — a real tough guy who plays politics like chess. But in every new twist and turn of the McDonald shooting, Emanuel has appeared to act only after he was backed into a corner by political pressure.
"I think the problem is that a lot of what's happening now seems reactive," said Vanessa Williamson, a fellow at the Brookings Institution.
Consider the timeline of how we got to this point of Emanuel apologizing:
The police department fought for months to keep the video from being released until a judge finally decided it should be. On the same day the grisly video was released, the county prosecutor charged the officer in question, Jason Van Dyke, who is white, with the murder of McDonald.
The charges came 13 months after the shooting. Critics cried foul, alleging that the city and police had tried to cover it up. Emanuel was forced to write an op-ed in the Chicago Tribune denying accusations he ordered the video held from public view until after he won a tough reelection race in April.
"I own the problem of police brutality, and I'll fix it," he promised.
But around the same time, Emanuel called a Justice Department investigation of the Chicago Police Department "misguided," even though Illinois' state attorney, one of its U.S. senators and its governor — as well as Democratic presidential front-runner Hillary Clinton— all said it was merited.
The next day Emanuel clarified his comments about the investigation: "We have a long road ahead of us as a city, and I welcome people from many views to help us do exactly what we need to do."
Making matters worse was the fact that, at the beginning of all this, Emanuel suggested the shooting was the act of a single bad apple — not, as The Washington Post editorial board noted, the act of a police department that fatally shoots more people than any other in the nation.(An update: In The Washington Post database of fatal police shootings, Chicago has 6 fatalities this year, behind Los Angeles (16), the Los Angeles sheriff (12), Miami, San Diego, New York, Las Vegas (each with 8), Oklahoma City (7) and the Riverside County sheriff (7).)
Undermining his argument even further were accusations that the police allegedly destroyed evidence by trying to delete footage of the shooting from security cameras at a nearby Burger King.
In a sense, the whole world seemed to know what Emanuel didn't seem to want to admit up front: The Chicago Police Department has a problem.
He has, however late, since come to say just that. He fired the city's police chief, set up a task force that promises to be independent, and on Wednesday gave that heartfelt speech.
But those actions don't change the fact that Emanuel appeared defensive at nearly every turn to get there. However sincere he might be when it comes to fixing the city's problems, Chicagoans can understandably now view his next steps through a lens of political opportunism rather than thoughtful leadership.
As such, a quick fix for Emanuel to help improve relations with his city — fire more people, give more speeches, hosts roundtables, invite even more federal investigations — is increasingly difficult to conjure.
"There may be some brilliant political play here," Williamson said, "but I think the time of political plays has passed."
The natural thing to do would be to spend time in Chicago's community rebuilding trust — listening to people instead of talking to them, Williamson calls it, stressing that Emanuel's first priority should be how to keep Chicago governable rather than how to keep his job.
But mending relationships takes time, and as the protests on the streets of Emanuel's beloved city make clear, the time for sincere action from Chicago's mayor might have already passed in the eyes of those who matter.