[15][16] Milwaukee police previously attracted controversy for two incidents involving the deaths of black suspects while in police custody—one in 2010 and the other in 2011[16]—as well as a scandal involving illegal strip searches and body cavity searches of 74 black people, for which a $5 million settlement was approved by the Milwaukee Common Council.

[17][18] Residents have criticized policing methods in predominantly black neighborhoods, which they say often involve a lack of respect towards suspects and use of force.

[19] On June 29, 2016, police in riot gear had to respond to unrest in Sherman Park, near 39th and Burleigh, a block away from the August incident.

[20] A BP gas station had been a frequent flash-point for unrest during June and July 2016, with several incidents taking place there, including a murder.

The man's handgun, along with 500 additional rounds of ammunition, had been reported stolen during a March burglary in nearby Waukesha.

[31][32] According to his grandfather, Smith had cognitive and mental health issues, needing to take special education classes in elementary and middle school.

This charge was followed by felony witness intimidation, when Smith attempted, through his girlfriend, to get the victim to sign a letter recanting his account.

[33][34] Smith's family said he had, at some point, filed a lawsuit against the Milwaukee Police Department, but no evidence of such a suit—settled or pending—was found in state or federal court.

[38] He was identified by the public on August 16 after at least 3,000 people shared a Facebook image of him, with some adding threatening comments; the post was deleted by Milwaukee police shortly after.

[35][36] On August 14, Milwaukee Police Chief Edward A. Flynn said Heaggan-Brown's "body camera showed Smith had turned toward the officer with a gun in his hand".

[9][15][22] The Revolutionary Communist Party confirmed that some of its members were among the protesters and that they traveled to Milwaukee to "support a revolution" but did not intend to incite violence.

[22] An O'Reilly Auto Parts shop, a beauty supply store, and the local branch of BMO Harris Bank were also set on fire in the area.

[2] In the early hours of August 14, Mayor Barrett and other local officials urged residents at a press conference to help restore order.

[15] In the afternoon, about 100 people, mostly black, held a peaceful demonstration in front of the O'Reilly Auto Parts shop that had been burned during the riot.

[52] Chief Edward Flynn said that the department's ShotSpotter system recorded a total of 30 instances of gunfire on the night of August 14.

[53] By the morning of August 15, fourteen more people were arrested and four police officers were wounded, including the one hit by the rock smashing a windshield.

[25][53] City officials refused to release the police body camera video showing Smith's shooting[55] pending the approval of the state Department of Justice.

[4] On August 23, Wisconsin Attorney General Brad Schimel said that releasing the video soon "would compromise the integrity of the investigation" and that it will not be unless charges are filed.

[37] After the first shot was fired, the video reportedly shows Smith throwing his gun away and falling, in a half-backwards roll, to the ground on his back, unarmed, with his legs and arms moving towards his head.

[57] On December 15, 2016, ex-officer[41] Dominique Heaggan-Brown was charged with first-degree reckless homicide stemming from Smith's death[8] "under circumstances showing utter disregard for human life", as defined by Wisconsin state law.

The judge thereby denied the defense's motion for a venue change and refuted the argument that pre-trial publicity, alleged anti-police sentiment, and prior police-involved shootings might prevent the defendant from getting a fair trial.

[12] As the selection began, the court mandated that the jury be sequestered[12] and that the jurors, both potential and actual, remain anonymous except to the prosecutors and defense.

[12] During the trial, prosecutors argued that the second shot fired by Heaggan-Brown was unjustifiable since Smith was already on the ground gun-free, wounded and therefore unable to escape or resist, so the officer's fear for his life was unfounded.

[14] On October 28, 2020, the city of Milwaukee and the family of Sylville Smith agreed to settle the ongoing lawsuit for $4 million.

[28] Milwaukee County Sheriff David Clarke wrote a controversial op-ed for The Hill, in which he blamed the riots on President Obama and liberals.

[32] Sherelle Smith's encouragement of violence in the suburbs was controversially edited out of initial online and televised reports by CNN, which were later updated to include her full statement.