Law enforcement authorities fatally shot Winston Boogie Smith Jr., a 32-year-old black American man, in the Uptown area of Minneapolis at 2:08 p.m. CDT on June 3, 2021. Smith was being pursued by a U.S. Marshals Service task force that apprehends wanted fugitives. The arrest operation had the participation of undercover agents from several local police agencies in Minnesota. The officers did not use body cameras or dashcams when apprehending Smith. Controversy over the lack of law enforcement footage of the arrest operation led to local police agencies ceasing aid to the Marshals Service's fugitive task force, and to changes to body and dash camera policies by the Marshals and other federal law enforcement agencies.

Several protests were held in reaction to Smith's killing, beginning on June 3, and the Uptown area experienced civil disorder over the subsequent weeks. Deona Marie Knajdek was killed and three others were injured on June 13 after a man rammed his vehicle into a group of demonstrators who had blockaded a street. In the immediate aftermath of the shooting, law enforcement authorities said publicly that Smith failed to comply with arresting officers and had brandished a gun. An attorney for the passenger in the vehicle with Smith contradicted the law enforcement description of events. The passenger had not seen a gun on Smith or in the vehicle, which was contrary to a video that later surfaced of the incident.

An investigation of law enforcement conduct by the Minnesota Bureau of Criminal Apprehension (BCA) after the shooting said that Smith had brandished a firearm at officers who attempted to arrest him. Authorities said they found a loaded 380 handgun with matching spent shell casings in the vehicle Smith occupied, and that ballistic evidence and DNA samples supported their claim that Smith had fired the weapon during the June 3 encounter. The report also revealed that the passenger had ducked for cover after pleading with Smith to surrender and that she did not visually witness the exchange of gunfire.

The BCA sent the case to the Crow Wing County attorney's office to determine if the officers who shot Smith should face criminal charges. In his report, Donald Ryan, the attorney for Crow Wing County, said that the officers' actions were justified under Minnesota Statutes and that no criminal charges should be filed against them. During the investigation and for several years afterward, it was believed that there was no video evidence of the shooting, but a private investigation as part of a civil suit was able recover a 35-second video filmed by Smith on his cellphone. The video, which was released publicly in 2025, recorded Smith saying, "Just shoot," shortly before law enforcement officers began to smash open the vehicle window. He is then seen grabbing a handgun from the vehicle's center console and exchanges gunfire with the officers. After a second review of the incident, the Hennepin County Attorney's Office also declined to prosecute the officers involved.

Winston Boogie Smith Jr. was a 32-year-old black American man who resided in Saint Paul, Minnesota. He spent his early life in south Minneapolis. He attended Coon Rapids High School. As a musician, he went by the nickname Wince Me Boi. He was also known for comedy videos and performance activism that he posted online. Smith was a father of three.

Smith was convicted previously of first-degree aggravated robbery related to a 2017 assault and robbery of his ex-girlfriend. He was sentenced to a 48-month prison term but was released on parole. The conviction also barred Smith from possessing a firearm. Smith was arrested on a probation violation in November 2019 when officers found a loaded handgun under the driver's seat of his car. He was subsequently charged in Ramsey County court for illegally possessing a firearm. Smith pled guilty to the weapons charge in November 2020 on the day before the trial was scheduled to start. Smith later sought to withdraw the guilty plea, which would have resulted in four years of prison time, but was denied by a judge.

In 2020, police in Bloomington, Minnesota, attempted to arrest Smith on several local warrants. Smith, who was in a parking lot at the Mall of America, allegedly fled in his vehicle. At the same time, police gave chase on Interstate 494 as Smith allegedly drove at high speed in the opposite direction of traffic. Police ended the pursuit due to concerns over public safety. Smith later faced charges in Hennepin County related to the incident and had a court hearing scheduled for September 2021.

Smith missed a May 19, 2021, sentencing hearing, and a new warrant in Minnesota was issued for his arrest, and he was ordered to be held without bond or bail. An internal police document included a quote from Smith that he might "shoot it out" if authorities tried to apprehend him. Smith had been active on social media, where in addition to posting his music, comedy sketches, and photos of family and friends, he had been outspoken about police killings of black men, such as George Floyd and Daunte Wright. He also spoke about his own upcoming sentencing, not wanting to spend four years in jail, and how he was not guilty of the weapons charge he was facing. He also compared his situation to video footage he had seen of Dolal Idd, a Somali-American man who was killed by Minneapolis police in an exchange of gunfire on December 30, 2020. Two of Smith's postings to social media had suggested support for violence against police.