[Update, Nov. 1: Heaggan-Brown has been fired by the Milwaukee Police Department after an internal investigation related to those criminal charges.]

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Police said a man told authorities he was sexually assaulted by Heaggan-Brown while turmoil still dominated Milwaukee’s streets two days after the officer killed Sylville K. Smith, 23.

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In court documents, authorities say the man told police that the officer, who was off-duty, had raped him at about the same time that other Milwaukee officers were responding to reports of gunshots, making arrests and having rocks thrown at them in the area of the demonstrations.

Investigators looking into the man’s allegation said they also found evidence that Heaggan-Brown had sexually assaulted a second man and paid for sex with two others. Edward A. Flynn, the Milwaukee police chief, called the charges “extraordinarily disappointing” and said they cast a pall over the department.

“It’s altogether awful,” Flynn said during a briefing Thursday afternoon. He said the officer had “revealed his character” in a way the department did not see when hiring him, and added: “It’s grave and we’re treating it as such.”

Heaggan-Brown shot Smith on a Saturday in mid-August, prompting an eruption of violence that stretched for hours that night and into early Sunday morning. While things were less volcanic as the tension continued Sunday night, violence continued to break out, as an 18-year-old man was shot in the neck in the Sherman Park area where the demonstrations were centered. Seven law enforcement officers were also injured that night, police said.

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According to the complaint, the man who said he was raped told police Heaggan-Brown had picked him up at the same time that the 18-year-old was shot near the protests. The two men went to a bar, where they “sat and watched television, as coverage of the Sherman Park protests aired,” according to a criminal complaint filed Thursday in Milwaukee County Circuit Court.

The following day, police were contacted about the report of an assault involving an officer, even while city officials were attempting to tamp down the simmering rage in the city sparked by the shooting. They announced plans for a limited curfew beginning later that day, following two nights during which buildings were set on fire and officers injured.

Police were also pushing back against suggestions circulating in the city that Smith was unarmed and shot in the back when he died after a traffic stop two days earlier. Officials said Smith had run from a traffic stop before turning to the officer while holding a gun. The shooting remains under investigation, and court documents made no connection between that incident and the sexual assault charges.

The complaint filed Thursday stated that Heaggan-Brown and the man who told police he was raped had connected through Facebook because they were both musicians. When they went to the bar, the complaint said the officer had “bragged about being able to do whatever [he] wanted without repercussions.”

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The Milwaukee police union did not respond to a request for comment about the charges. A defense attorney listed in court records as being with Heaggan-Brown in court on Thursday did not immediately respond to a request for comment.

Surveillance video shows that Heaggan-Brown and the man accusing him spent a little more than an hour-and-a-half drinking at the bar that night, according to the complaint.

In a police interview described in the complaint, the man — who was not identified — told police that he had difficulty remembering what happened after he left the bar and described waking up to being assaulted. The man told police that he tried to move away and said no, but told authorities he felt drugged and threatened. The complaint stated that this man “exhibited signs of trauma” during his interview.

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Hospital surveillance video showed that the two men arrived at the hospital at about 4:16 a.m. and that the officer left a little more than 20 minutes later, police said.

A nurse at the hospital who attended to the man said Heaggan-Brown had told her that this man “began to act weird and unresponsive” at the bar, which is why the officer said he brought him to the hospital. The nurse also told police that the man became very agitated, yelling that he had been raped by the person who took him to the hospital.

Later that morning, police said Heaggan-Brown sent a text message to Sgt. Joseph Hall, another Milwaukee officer who had mentored him.

In the text, police say Heaggan-Brown described having “a separate situation” and saying he had messed up “big time,” adding: “But need to handle this the most secret and right way possible.”

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Hall later met with Heaggan-Brown and, according to the complaint, the officer described the sex as consensual but acknowledged that the man who said he was raped “was drunk and had ‘medical issues.’”

Authorities were investigating Hall and this communication “to get to the bottom of just what that exchange was about,” Flynn said.

Nearly a week after police interviewed the man who said he was raped, they reached out to Heaggan-Brown. The complaint said he handed over his phone and agreed to let officers search his home, but when they arrived, police found that most of his belongings had been moved out. Heaggan-Brown also told police he had the man’s shirt, belt and phone in his car, which officers recovered.

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The sexual assault charges each carry a possible sentence of up to 40 years in prison as well as potential fines of up to $100,000.

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While searching Heaggan-Brown’s phone after the initial complaint, authorities then said they discovered evidence he had tried to offer two other people money for sex. They also found images of what the complaint stated were nude photos of another person, some showing sexual contact. This person told police they did not consent to any sexual contact or the nude photos, the complaint stated.

In addition to the assault charges, Heaggan-Brown has also been charged with two counts of prostitution, a misdemeanor, and a felony count of taking a nude photo of someone without their consent.

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Heaggan-Brown, also named as Dominique Heaggan in some media reports, has been described as a young father who had attended the same high school as Smith. He has been suspended by the department with pay, officials said Thursday.

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Flynn, the police chief, said that Heaggan-Brown remains in custody. He also said the officer has been charged internally for violating the department’s code of conduct and will face disciplinary proceedings.

According to court records, when Heaggan-Brown appeared before a judge Thursday he pleaded not guilty to the misdemeanor counts in the complaint. The judge set cash bond at $100,000, told Heaggan-Brown not to contact any of the victims in the complaint and ordered the county sheriff to get a DNA sample from the officer. Heaggan-Brown is scheduled to appear in court next Thursday.

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