Gold Coast carjackers have extensive criminal backgrounds, both previously convicted of carjacking: officials

Charles Benson (L), Demontae Watkins, and a U.S. Customs and Border Protection helicopter similar to one that occasionally teams up with the Chicago vehicular hijacking task force. | Chicago Police Department; U.S. Customs and Border Protection

CHICAGO — The two men who went on a 20-minute violent crime spree in the Gold Coast this week developed extensive violent crime backgrounds as juveniles, officials said, with one being on parole and the other being off parole for about a month.

Those are some of the new details that emerged as Charles Benson, 20, and Demontae Watkins, 18, were detained by Judge Charles Beach at the Leighton Criminal Courthouse.

“Give me your keys, b**ch,” Watkins allegedly barked while pointing a handgun toward a 26-year-old woman in the 1500 block of North State around 7:30 Tuesday evening.

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 duo 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 his 2008 Audi, they took the victim’s 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 CPD 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. 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.

Judge Charles Beach detained both men, citing their extensive criminal backgrounds as one reason they did not qualify for pretrial release.

Benson had been off parole for about 30 days at the time of the crime spree, Beach wrote in his detention order. Benson’s 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.

Watkins is currently on parole, according to Beach’s order. The judge noted Watkins had a 2023 juvenile adjudication for vehicular hijacking with a firearm and a total of eight 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.

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About Tim Hecke 324 Articles
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