Prosecutors filed criminal charges Thursday against the man alleged of shooting at police and killing his girlfriend at an apartment complex in Broomfield earlier this month.

The 17th Judicial District Attorney’s Office charged 34-year-old Gregory Ryan Miles with one count of first-degree murder, four counts of attempted first-degree murder and 18 counts of attempted first-degree murder of a peace officer, stemming from the shootout that occurred on Sept. 12, according to a news release from the district attorney’s office.

Officers responded to the Arista Flats apartments on Central Court — near the 1stBank Center between U.S. Highway 36 and Wadsworth Parkway — around 6:30 a.m. that day after receiving a report from a neighbor.

Upon arrival, officers heard a man — later identified as Miles — making threats and then gunshots.

The incident turned into a nearly four-hour standoff between Broomfield Police Department officers and the man, with Miles allegedly firing multiple shots from the apartment at officers, vehicles and nearby units.

The suspect busted out one of the windows, leaned out and unloaded a full clip toward the police, Anthony Rurupe, a nearby resident, told The Denver Gazette.

“It didn’t really look like he was trying to aim at anybody. It looked like he was just indiscriminately unloading on anything to the west,” he said.

SWAT officers eventually forced entry into the apartment. One officer fired his weapon at the suspect, hitting him multiple times. The officers were then able to detain the man, the department said following the arrest.

One victim, 32-year-old Aisha Yvonne Quest, was taken to a nearby hospital where she later died from her injuries, resulting in the first-degree murder charge.

Her family told The Denver Gazette’s news partner, 9NEWS, that they believe she was in relationship with Miles.

Miles’ criminal history shows a  trail of domestic violence.

Multiple women were listed as protected parties on protection orders against him since 2021 and Miles was ordered to not have a gun at least twice.

Miles pleaded guilty in Jefferson County for violating a protection order. At least three women — not including Quest — were named as protected parties in similar orders.

A girlfriend told the Adams County court in 2012 that she didn’t want Miles to have a gun, 9NEWS reported. The court then filed a mandatory protection order after Miles forced his way into her home breaking the front door. He pleaded guilty to criminal mischief.

A third woman was granted a mandatory protection order in Denver in 2019 after Miles was charged for having, or trying to buy, a gun or ammunition while a protection order was in effect.

In January 2020, Miles pleaded guilty to a misdemeanor charge for violating a protection order. Another charge for violating bond conditions was dismissed by the district attorney’s office.

In August 2020, he was charged in Douglas County for assaulting the same woman in the Denver case. In 2021, he pleaded guilty to misdemeanor assault.

Miles has also been found guilty of being drunk with a gun, driving while impaired and theft in his destructive past.

Now, Miles faces his most serious charge — potentially facing life in prison.

The Denver Gazette’s news partners 9News contributed to this report.