Rahm Emanuel says he’s sincere in his desire to reform the city of Chicago's police department and mend its relationship with citizens, especially blacks and Hispanics. But whether or not residents believe him is likely to depend on whether or not they find his past behavior credible—and that’s becoming an ever more serious problem for the mayor.

On Thursday, the Chicago Tribune published a damning report suggesting that despite Emanuel’s protestations of ignorance about the shooting of Laquan McDonald, his top staffers were aware of how the 17-year-old black youth was killed and of the videotape of his shooting by a police officer months before the mayor says he found out. And Thursday afternoon, the city released a video of a separate shooting: this one on January 7, 2013, of Cedrick Chatman, a black teenager shot by a Chicago police officer after he ran from a stolen vehicle. The city had been trying to prevent the video’s release, but on Wednesday abruptly changed course and said it would not object to making it public. A federal judge scolded Chicago’s lawyers for their lengthy obstruction followed by the city’s 11th-hour reversal. The McDonald video itself was released only after a judge’s order.

Chatman’s family has filed a wrongful-death suit against the city. Officer Kevin Fry shot at Chatman four times, hitting him twice, after the 17-year-old bolted from the car. Fry said he fired because he believed Chatman had a gun and was about to fire at his partner, Officer Lou Toth. The teen was carrying an iPhone box. The shooting was investigated by the Independent Police Review Authority, which has come under intense scrutiny in the McDonald case, with its chief forced to resign. The IPRA investigator, Lorenzo Davis, found the shooting unjustified, but his bosses overruled him and cleared Fry. Davis was fired and has sued.

The video, shot from a surveillance camera on the corner, doesn't offer the same immediacy as the dashcam footage of McDonald’s killing. Around 5:30 in the clip below, Chatman can be seen running, with Toth in pursuit. Then Fry fires. As a firetruck arrives (around 6:30), Toth can be seen standing over Chatman’s body, which lies in the street near the curb. Lawyers for Chatman’s family said Toth had his foot on the boy’s neck.

The Chatman case provides just the latest example of a police department where officers seem to shoot unarmed civilians of color with no repercussions. And as the Tribune story shows, questions about the McDonald case will continue to haunt the mayor's office.

Emanuel’s critics charge that he tried to bury the video of that shooting—which showed Officer Jason Van Dyke shooting McDonald repeatedly in the back and on the ground—for political reasons. Emanuel, a Democrat, faced a challenging reelection campaign in 2015, having alienated many progressives by closing schools and failing to prevent a crime spike. The city painstakingly fought to keep the video private. On February 24, Emanuel failed to win enough votes to keep his seat outright, and he was forced into a runoff election. Three days later, lawyers for the McDonald family began talking to city lawyers about a settlement.

On April 7, Emanuel triumphed in the runoff, winning a second term, and eight days later the city council quickly approved a settlement with the McDonald family. A judge finally ordered the video’s release on November 19. The footage created a national uproar and instigated marches in the streets of the Windy City. Van Dyke has been charged with first-degree murder. Several days later, Emanuel removed his police chief, Garry McCarthy, in a move that critics both welcomed and derided as scapegoating.

Emanuel says he only saw the video when it was made public, and only came to understand the details of the case at the end of March—thus exculpating him for any political motive. The Tribune casts doubt on that claim:

But interviews, official city calendars and emails show in both cases the mayor's closest aides and City Hall attorneys knew much earlier than that. Emanuel's top staffers became keenly aware the McDonald shooting could become a legal and political quagmire in December 2014—more than three months before the mayor has said he was fully briefed on the issue. And lawyers for McDonald's family informed Emanuel's Law Department in March that police officers' version of what happened differed dramatically from the infamous shooting video—more than eight months before the mayor said he found out about the discrepancy and well after he agreed to settle the case for $5 million.

In a statement to the Tribune, Emanuel’s spokesman argued these meetings were routine, and wouldn’t have involved the McDonald case: “What you’re talking about are routine meetings between the mayor and police superintendent on crime reduction strategies, and the mayor and the corporation counsel on a wide range of legal matters.”

The story, which comes with a very helpful timeline, creates a difficult bind for Emanuel: Either he’s lying about when he learned about the McDonald shooting, or the situation in his office is such that top aides were not keeping him informed about a matter of such seriousness that it resulted in a $5 million payout and a murder charge against an officer. In other words, Emanuel wants to convince Chicagoans that he’s not dishonest; he’s just bad at managing, which happens to be his job as mayor. (He’s not the first politician to make this case.) Even those who give him the benefit of the doubt are bound to wonder whether better management of the situation might have prevented other police shootings and brought about accountability sooner.

Meanwhile, Emanuel is beset on various sides. He has vowed to improve his responsiveness and acknowledged shortcomings. State lawmakers have introduced a bill that would allow Chicagoans to try to recall the mayor, and Governor Bruce Rauner—a Republican, but a one-time pal of Emanuel’s—has said he is “very disappointed” in the mayor and would not veto the bill if it reaches his desk.

A quick glance at the headlines in Chicago Thursday offers a snapshot of why Emanuel finds his position suddenly so tenuous. In addition to the questions about his handling of the McDonald case and stories about the Chatman video, the Tribune has a report on the shooting of Quintonio LeGrier and Bettie Jones by police and on the “deadly start to the new year” in Chicago. Another item notes that the Cook County Democratic Party has endorsed a challenger to district attorney Anita Alvarez, who has also come under fire for being slow to charge Van Dyke in the McDonald shooting; she brought the charges only the day the video was released.

There continue to be calls for Emanuel’s resignation. Meanwhile, Emanuel is searching for a new police chief, even as the city and department face a U.S. Department of Justice investigation. A top police expert told The New York Times the post was “the most challenging job, police chief job, in the country right now.” But taking over the Chicago Police Department might be easier than Emanuel’s job right now.