Waukesha jail window broken, inmate accused of having gun near school

Asahel Ali

A Waukesha man, currently being held at the Waukesha County Jail after prosecutors said he was armed with a rifle a block from Waukesha North High School in April 2023, is facing a new charge. 

Asahel Ali is now facing a charge of criminal damage to property. Prosecutors said he broke a window in his jail cell on Feb. 6. 

According to the criminal complaint, surveillance video shows Ali kicking the window several times and walking around his cell. The video then shows Ali picking a tray up off the ground and throwing it at the window. 

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It is estimated that the window will cost $336 to fix, per the complaint. Ali refused to speak with officers following the incident, according to the complaint.

Gun near Waukesha high school case

Ali is charged with second-degree recklessly endangering safety, resisting an officer (causing soft tissue injury), negligent handling of a weapon and felony bail jumping after prosecutors said he had a gun near a schoo. He was 17 years old at the time.

Shortly before 12:30 p.m. on April 14, 2023, Waukesha police said students saw the teen with a rifle in the backyard of a home one block from the high school. According to a criminal complaint, the student reported the armed teen had a pillowcase over his head with two holes cut out for eyes and was crouched down aiming the gun as if "pointing to shoot at a squirrel." A witness told police they saw the same thing, but that they also saw the gun at one point aimed toward the high school.

Police deployed a "significant" presence to safeguard area schools and, once they were secured, searched for the teen. Based on prior encounters, an officer believed Ali may have been the teen involved. There was a March 23 incident in which he tried to get into Waukesha North High School, even though he is not a student there. The same officer saw Ali the morning of April 14 "acting bizarre in his front yard waving a baseball bat around."

Rifle recovered from 17-year-old in Waukesha

Ali was found a short time later in the backyard of his home near the school armed with the rifle. After talking with the teen, police said he peacefully surrendered to officers and was taken into custody without further incident. The gun and a 30-round magazine were recovered. The complaint states a bullet hole was found in the living room of Ali's home near the school. The bullet was lodged inside a neighbor's garage, and he had the spent casing in his pocket.

"I don’t think it’s quite as aggravated as the community initially thought," the defense said in court Wednesday for Ali's initial appearance.

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The complaint states Ali was taken to a hospital where, while handcuffed, he repeatedly said "I'm free." He became "physically resistive" there and scratched an officer, who was treated at the hospital for a laceration.

At the time of the Waukesha incident, court records indicate he was already out on bail for a Milwaukee County case – charged last year with taking and driving a vehicle without consent. He was ordered not to possess any dangerous weapons or firearms as a bail condition.

"As young as you are, you have had a lot of contact with the criminal justice system," the court commissioner said. "I don’t think I have any option but to place high cash bond in this case."