Two men with lengthy juvenile criminal records, including prior carjacking adjudications, were sentenced to 16 years in prison on Thursday for a violent Gold Coast crime spree that included beating a woman, attempting to carjack a man outside Gov. J.B. Pritzker’s mansion, and ultimately stealing a food delivery driver’s car at gunpoint.
Demontae Watkins, 20, and Charles Benson, 23, pled guilty before Judge Neera Walsh to charges coming from a 20-minute binge on January 16, 2024, that ended with both men fleeing in a stolen Nissan as police helicopters trailed them from above.
The incident began around 7:30 p.m., when the two approached a 26-year-old woman in the 1500 block of North State Street. Watkins allegedly held a handgun at her and demanded her keys and belongings before the guys forced her to the ground and kicked her repeatedly, including in the face, prosecutors claim.
They abandoned their hijacking attempt when a passing car frightened them.
However, the pair attacked again minutes later on the 1400 block of North Astor Street, just steps from Pritzker’s mansion. A 41-year-old guy was seated in his 2008 Audi when two men climbed inside, brandished pistols, and demanded his wallet, according to police. The victim handed over his belongings and exited.
The carjackers then encountered a problem: they couldn’t drive a manual shift. So they abandoned the man’s Audi and set off on foot.
They discovered a more appropriate target in the 1000 block of North Lake Shore Drive: a 33-year-old food delivery driver. Prosecutors claimed they pulled a gun on him and took his 2019 Nissan Sentra, with Benson getting behind the wheel and driving south.
However, the Nissan had hardly begun its escape when it began pinging the city’s extensive network of license plate scanners. The Chicago Joint Vehicular Hijacking Task Force was conducting a special operation that night, and Illinois State Police troopers pursued it on the ground while CPD and US Customs and Border Protection aircraft watched it from above, according to court records.
Prosecutors said Benson finally accelerated the automobile to more than 90 mph on the Dan Ryan Expressway. The chase concluded in the 7000 block of South Wood Street, where the two males jumped out and fled. According to police documents, the CPD helicopter assisted officers in locating Benson, who was hiding under a stairwell. An ISP dog tracked down Watkins, who was sleeping in nearby bushes. Police claimed a loaded firearm was lying near Watkins’ feet.
Despite their young ages, both guys had substantial histories, according to officials.
Benson had barely been released from parole for a firearms case for around 30 days when he joined Watkins on the Gold Coast rampage, according to a court filing. His juvenile record included convictions for carjacking, possession of a stolen motor vehicle, robbery, reckless conduct, and aggravated robbery with a pistol, according to authorities.
Watkins was still on parole. He was declared delinquent in 2023 for armed carjacking and had eight arrests, according to prosecutors. These charges allegedly included assault, domestic battery, electronic harassment, criminal damage to property by explosion, and two counts of criminal trespass to a car.
According to authorities, Watkins carjacked someone else on the South Side approximately an hour before the Gold Coast spree began. In that case, he allegedly approached a man who had recently parked in the 7200 block of South Winchester Avenue. Wearing a mask and black clothing, Watkins allegedly pushed a revolver against the man’s side and demanded the keys to his 2002 Honda.
On Thursday, Watkins pled guilty to aggravated vehicle hijacking with a weapon, aggravated battery in a public place, attempted aggravated vehicular hijacking with a handgun, armed robbery, and aggravated unauthorized use of a weapon. He received penalties ranging from five to sixteen years, all served consecutively.
Benson pled guilty to aggravated vehicular hijacking with a weapon, aggravated battery in a public place, attempted aggravated vehicular hijacking with a firearm, aggravated vehicular hijacking with a weapon, and illegal possession of a stolen vehicle. He also pled guilty to two charges he received while in Cook County Jail: possession of cannabis in a prison institution and arson.
Like Watkins, his pleas resulted in concurrent sentences of varied lengths, the longest being 16 years.
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