A man already in jail on charges he tried to sexually assault a woman in September has been accused of attacking an employee of a horse-drawn carriage company a month earlier in West Town.
Dennis Jackson Jr., 23, faces new felony counts of aggravated criminal sexual assault and armed robbery in the attack in August, according to Cook County prosecutors.
Judge Stephanie Miller ordered Jackson, of Lawndale, held without bail on the new charges Friday when he appeared for his initial hearing at the Leighton Criminal Court Building.

Dennis Jackson | Police
In September, Jackson was charged with armed robbery, kidnapping and attempted sexual assault after he allegedly forced a woman into a gangway between homes in West Town and ordered her to take off her clothes. She escaped, but he was arrested and pleaded not guilty to the charges, court records show. At the time of his arrest, Chicago police said Jackson was wanted in connection with a series of robberies in the Near West Side District.
The new case, prosecutors said, took place Aug. 14 when Jackson approached a 33-year-old woman who was pulling a horse-drawn carriage into the company’s staging area in the 2000 block of West Ferdinand Street. While the woman was putting away her horse, Jackson allegedly pulled out a gun and demanded money.
After taking the money, he demanded the woman take off her clothes and sexually assaulted her, prosecutors said. At one point, Jackson allegedly asked the woman if she had a condom. When she said she didn’t, he asked if she had a rubber glove.
The woman was ordered into the barn to look for a glove and went to a medicine cabinet near a company safe, prosecutors said. Jackson demanded that she open the safe, but she did not have the combination. Jackson told her to call her manager for the numbers, prosecutors said.
The woman called her manager and tried several times to open the safe, but was not successful. Prosecutors said Jackson ran off during that time and the manager called police.
In November, the carriage employee identified Jackson in a photo array, prosecutors said.
Surveillance footage also showed Jackson fleeing the area and semen was collected that was “suspected to be” Jackson’s, prosecutors said.