Two men with extensive juvenile criminal backgrounds, including past carjacking offenses, received 16-year prison sentences on Thursday following a violent crime spree in Gold Coast. The incidents involved assaulting a woman, attempting a carjacking near Gov. J.B. Pritzker’s mansion, and ultimately stealing a food delivery vehicle at gunpoint.
Demontae Watkins, 20, and Charles Benson, 23, admitted guilt in front of Judge Neera Walsh for their actions during the spree on January 16, 2024. This spree, which lasted about 20 minutes, concluded with the duo escaping in a stolen Nissan, tracked by police helicopters.
The series of crimes commenced around 7:30 p.m. when the pair confronted a 26-year-old woman on the 1500 block of North State Street. Watkins allegedly pointed a firearm at her, demanding her keys and valuables, before both men pushed her to the ground and kicked her, including in the face, according to prosecutors.
Their attempt was thwarted when a passing vehicle interrupted them.
Shortly thereafter, in the 1400 block of North Astor Street, near Pritzker’s mansion, they targeted a 41-year-old man sitting in his 2008 Audi. The men entered the vehicle, brandished weapons, and demanded his wallet, according to police. After the victim complied, the men fled.
However, they ran into trouble as neither could drive a manual transmission, leading them to abandon the Audi and flee on foot.
They soon encountered a more suitable target on the 1000 block of North Lake Shore Drive: a 33-year-old food delivery driver. Prosecutors stated they threatened him with a firearm and stole his 2019 Nissan Sentra, with Benson driving south.
The Nissan was quickly detected by the city’s license plate reader network. The Chicago Joint Vehicular Hijacking Task Force was conducting an operation that evening, prompting Illinois State Police troopers to give chase on the ground while CPD and U.S. Customs and Border Protection helicopters tracked it from above, court records show.
Benson reportedly accelerated the car to over 90 mph on the Dan Ryan Expressway. The pursuit concluded in the 7000 block of South Wood Street, where both men abandoned the car and fled. A CPD helicopter assisted in locating Benson hidden under a stairwell, while an ISP canine unit found Watkins hiding in nearby bushes with a loaded handgun at his feet, police reported.
Officials noted both men had significant criminal histories despite their young ages.
Benson had completed parole for a gun charge only 30 days before the spree, a court document revealed. His juvenile offenses included carjacking, vehicle theft, robbery, reckless conduct, and aggravated robbery with a firearm, officials stated.
Watkins remained on parole, having been adjudicated delinquent in 2023 for armed carjacking and had faced eight arrests. These incidents allegedly involved assault, domestic battery, electronic harassment, property damage by explosion, and criminal trespass, prosecutors said.
Prosecutors also alleged Watkins carjacked another individual on the South Side approximately an hour prior to the Gold Coast spree. In that incident, he reportedly approached a man who had just parked on the 7200 block of South Winchester Avenue, allegedly pointing a gun at him to demand his 2002 Honda keys.
On Thursday, Watkins pleaded guilty to several charges, including aggravated vehicular hijacking with a weapon, aggravated battery, attempted aggravated vehicle hijacking with a firearm, armed robbery, and unlawful weapon use. He was sentenced to concurrent terms ranging from five to 16 years.
Benson admitted guilt to aggravated vehicular hijacking with a weapon, aggravated battery, attempted aggravated vehicle hijacking with a firearm, and unlawful possession of a stolen vehicle. Additionally, he pleaded guilty to possession of cannabis and arson while in Cook County Jail. His concurrent sentences also reached up to 16 years.
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