Man charged in Gold Coast robbery, carjacking spree earlier this year is linked to yet another hijacking

Demontae Watkins (Chicago Police Department)

CHICAGO — One of the men accused of going on a violent crime spree in the Gold Coast earlier this year has been linked to yet another violent crime that occurred that night. Prosecutors have now charged Demontae Watkins, 18, with carjacking another driver on the South Side about an hour before the Gold Coast crimes began.

Watkins was on parole when he walked up to a man who had just parked in the 7200 block of South Winchester around 6:30 p.m. on January 15, prosecutors said in a court filing. They said Watkins, wearing a mask and black clothing, put a gun to the man’s side and demanded the keys to his 2002 Honda.

Officials said surveillance video from a gas station showed Watkins getting out of the hijacked car a short time later. Judge Neera Walsh, who is handling the Gold Coast cases, detained Watkins on the new charges and noted that he had been convicted of four similar crimes. He was already detained in the pending cases.

About an hour after the carjacking, Watkins and Charles Benson, 20, arrived in the Gold Coast, officials claim.

Watkins allegedly confronted a 26-year-old woman in the 1500 block of North State, displayed a gun, and ordered her to “Give me your keys, b**ch.” He and Benson pushed the woman to the ground and kicked her in the face but eventually ran away when another car scared them, according to Chicago police.

Minutes later, the men allegedly tried to carjack a 41-year-old man near Gov. JB Pritzker’s home in the 1400 block of North Astor. Unable to operate the stick shift on the victim’s 2008 Audi, they instead took his money and credit cards and ran away.

A couple of blocks away, they successfully carjacked a 33-year-old food runner in the 1000 block of North Lake Shore Drive, prosecutors said. With Benson behind the wheel, the car sped toward the South Side, setting off a series of CPD license plate readers along the way. Cops tipped off the vehicular hijacking task force, which was running a special operation that night.

According to police documents, two helicopters, one run by Chicago police and the other by U.S. Customs and Border Protection, tracked the car as Illinois State Police troopers pursued it on the ground.

Benson reached speeds of “90+ mph in a 55 mph zone” on the Dan Ryan near Garfield, prosecutors said in his detention petition.

Both men bailed out of the car near 7000 South Wood, about four blocks from where Watkins allegedly committed the first hijacking. The CPD helicopter led officers to Benson, who was hiding under a stairwell, while a state police dog found Watkins lying in some bushes with a loaded handgun near his feet, the CPD reports said.

During a detention hearing in January, Judge Charles Beach noted that, in addition to being on parole, Watkins had a 2023 juvenile adjudication for vehicular hijacking with a firearm and a total of eight juvenile arrests. Those arrests included allegations of assault, domestic battery, electronic harassment, criminal damage to property by explosion, and two counts of criminal trespass to a vehicle.

Benson had been off parole for about 30 days at the time of the crime spree, Beach wrote in his detention order. His background includes unlawful use of a weapon, which is what he had been on parole for; a 2023 domestic battery arrest with an order of protection; and juvenile adjudications for vehicular hijacking, possessing a stolen motor vehicle, robbery, reckless conduct, and aggravated robbery with a firearm, Beach wrote.

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Tim Hecke is CWBChicago's managing partner. He started his career at KMOX, the legendary news radio station in St. Louis. From there, he moved on to work at stations in Minneapolis, Chicago, and New York City. Tim went on to build syndicated radio news and content services that served every one of America's 100 largest radio markets. He became CWBChicago's managing partner in 2019. His email address is