But despite all the criticism he has endured, Mayor Rahm Emanuel is comfortable with his response. In a one-on-one interview just days before he will leave office, Emanuel defended his handling of the case.
On a beautiful day along the Riverfront, Emanuel sat down to talk about one of the ugliest chapters in his eight years in office.
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"This is not the first police shooting in Chicago's history. But it is the shooting that's led to the biggest changes," said Emanuel.
McDonald was gunned down in October 2014, in the height Emanuel's re-election campaign. The city settled with the family for $5 million and the video was not released until a judicial order seven months after Emanuel was re-elected in April 2015.
Emanuel did not directly answer when asked if he believed he could have won re-election had the video been released prior to the election.
"It's all hypothetical, I don't know how to answer it. But I do know this as soon as the judge made a ruling, we stopped fighting," he said.
Investigative journalist Jamie Kalven, who first reported the existence of the dashcam video in February 2015, said that is not completely true.
"Again and again and again he has resisted reforms, he resisted the consent decree process that he has now embraced and is taking credit for as part of his legacy," said Kalven.
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Kalven is co-producing the Showtime documentary "16 Shots". It provides an in-depth investigation into the case of Laquan McDonald and the impact it made on the city.
"It would have taken extraordinary leadership to truly rise to the occasion. I don't think he provided that. I do think there has been progress made," Kalven said.
While Kalven is critical of Emanuel's leadership during the crisis, he said it's unfair to lay all the blame at his feet.
"If there's a key point, at least for me in the documentary, it's that we can have really evil outcomes without having evil people to point the finger at as the cause," said Kalven.
Emanuel said there was no cover up by his administration, and he has taken many steps to change the police culture.
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"There was no effort, and even the head of the black caucus, Rod Sawyer said there was no cover up. People have said that, I'm not going to change that, but I know what the facts are," Emanuel said.
When asked if he is satisfied with the reforms that have come out of this, and if he would like to see more done, Emanuel answered:
"I know the reforms we've made. Body camera with every officer, all 13,000 ahead of schedule. A taser to every officer, training associated with it, deescalation policies, separation of mental health from a crime."
Emanuel maintains he never saw the video until it was publicly released. He also maintains that the case did not play a role in his decision not to seek re-election.
Emanuel said he owned up to his mistakes and instituted changes that he believes will keep making a difference long after he leaves office.
While "16 Shots" will start airing on Showtime June 14, there will be a Chicago premiere showing on June 4 at 7 p.m. at the Logan Arts Center, at 915 E. 60th St.