Bartender gets 3 years for sexually abusing customer after plying her with drinks on the North Side

CHICAGO — A North Side bartender accused of sexually assaulting a patron after plying her with drinks she didn’t request has pleaded guilty to a lesser charge in exchange for a three-year sentence. Prosecutors said the victim didn’t know what happened to her until she went back to the bar and asked the manager to show her the night’s surveillance video.

Jose Callejas-Castillo, 31, pleaded guilty to Class 4 criminal sexual abuse, reduced from a more serious Class 2 charge, before Judge Stanley Sacks, according to court records. Prosecutors dropped 19 other felonies in the plea deal, including multiple counts of aggravated kidnapping and aggravated criminal sexual assault. 

The assault occurred inside a bar in the 5400 block of North Broadway on October 30, 2022, according to Chicago police records. Prosecutors did not identify the establishment by name during Callejas-Castillo’s initial court hearing.

They said a 25-year-old woman and her friend did not know Callejas-Castillo when they sat at the bar that night. He allegedly flirted with the woman and poured shots for her and her friend that they did not request.

The woman’s friend left around 11:23 p.m. By 12:13 a.m., prosecutors said, Callejas had provided the victim with nine shots.

Jose Callejas-Castillo | Chicago Police Department

At one point, the woman fell from her chair. Citing video footage, prosecutors said Callejas-Castillo walked from behind the bar to help her, then hugged and kissed her and pulled down her shirt to expose her breast.

The woman tried to leave, but the door was locked. Prosecutors said Callejas-Castillo led her to a bench in the vestibule and put the woman’s mouth on his exposed penis. Officials alleged that the woman did not appear to move as Callejas-Castillo pleasured himself.

Later, Callejas-Castillo texted his girlfriend, asking her to help him with an intoxicated customer. His girlfriend discovered the woman unconscious in the vestibule.

Another bar employee suggested calling an ambulance for the woman, but Callejas-Castillo insisted that they not, prosecutors said. Instead, prosecutors said, Callejas-Castillo’s girlfriend drove the victim home and then left her in a nearby building because they could not get into the victim’s complex.

The victim awoke the following day, Halloween, with a sore throat and bruises on her nose and leg. Prosecutors said she returned to the bar on November 1 to retrieve keys and a phone she thought she had left behind.

While speaking with the bar owner, the woman learned that Callejas-Castillo had quit, and she asked the owner to review surveillance video to learn what happened. The owner agreed and then informed the woman about what the footage showed, according to prosecutors. She went to an urgent care center and notified the police the same day.

Callejas-Castillo, who had worked as a bartender and manager for nine years, had never been arrested before.

His three-year sentence will be reduced to 18 months for good behavior. It will be reduced further by credits he earned while in jail and on electronic monitoring while the case was pending. He is expected to be paroled on June 21.

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