Two men with lengthy juvenile criminal records, including prior carjacking adjudications, were sentenced to 16 years in prison Thursday for a violent Gold Coast crime spree that saw them beat a woman, try to carjack a man outside Gov. J.B. Pritzker’s mansion, and finally steal a food delivery driver’s car at gunpoint.
Demontae Watkins, 20, and Charles Benson, 23, pleaded guilty before Judge Neera Walsh to charges stemming from the January 16, 2024, spree, which lasted about 20 minutes and ended with both men fleeing in a stolen Nissan as police helicopters tracked them from above.
It all began around 7:30 p.m. as the pair approached a 26-year-old woman in the 1500 block of North State Street. Watkins allegedly pointed a handgun at her and demanded her keys and valuables before the men pushed her to the ground and kicked her repeatedly, including in the face, prosecutors alleged.
They abandoned the hijacking attempt when a passing car startled them.
But the pair struck again minutes later in the 1400 block of North Astor Street, just steps from Pritzker’s mansion. A 41-year-old man was sitting in his 2008 Audi when the two men climbed inside, displayed guns and demanded his wallet, police said. The victim handed over his property and got out.
Then the carjackers ran into a problem: They didn’t know how to drive a stick shift. So, they abandoned the man’s Audi and took off on foot.
They found a more suitable target in the 1000 block of North Lake Shore Drive: a 33-year-old food delivery driver. Prosecutors said they pulled a gun on him and stole his 2019 Nissan Sentra, with Benson getting behind the wheel and heading south.
But the Nissan had barely begun its escape when it started pinging on the city’s vast network of license plate readers. The Chicago Joint Vehicular Hijacking Task Force happened to be conducting a special operation that night, and Illinois State Police troopers pursued it on the ground as helicopters from CPD and U.S. Customs and Border Protection shadowed it from above, according to court filings.
Benson eventually pushed the car to more than 90 mph on the Dan Ryan Expressway, prosecutors said. The chase ended in the 7000 block of South Wood Street, where the two men bailed out and ran. The CPD helicopter helped cops find Benson hiding under a stairwell, according to police records. An ISP dog sniffed out Watkins, who was lying in nearby bushes. A loaded handgun was lying near Watkins’ feet, police said.
Despite their relatively young ages, both men had extensive histories, officials said.
Benson had been off parole for a gun case for only about 30 days when he joined Watkins in the Gold Coast spree, a court filing said. His juvenile record included adjudications for carjacking, possessing a stolen motor vehicle, robbery, reckless conduct and aggravated robbery with a firearm, officials said.
Watkins was still on parole. He had been adjudicated delinquent in 2023 for armed carjacking and had accumulated eight arrests, according to prosecutors. Those cases allegedly included assault, domestic battery, electronic harassment, criminal damage to property by explosion and two counts of criminal trespass to a vehicle.
And prosecutors say Watkins had already carjacked someone else on the South Side about an hour before the Gold Coast spree began. In that case, he allegedly approached a man who had just parked in the 7200 block of South Winchester Avenue. Wearing a mask and black clothing, Watkins allegedly pressed a gun against the man’s side and demanded the keys to his 2002 Honda.
On Thursday, Watkins pleaded guilty to multiple counts of aggravated vehicular hijacking with a weapon, aggravated battery in a public place, attempted aggravated vehicular hijacking with a firearm, armed robbery and aggravated unlawful use of a weapon. He received sentences ranging from five to 16 years, all served concurrently.
Benson pleaded 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 unlawful possession of a stolen vehicle. He also pleaded guilty to two cases he picked up while in the Cook County Jail: possession of cannabis in a penal institution and arson.
Like Watkins, his pleas resulted in concurrent sentences of varying lengths, with 16 years being the longest.
