Bartender sexually assaulted woman in North Side tavern after plying her with free shots, prosecutors say

Chicago — A bartender sexually assaulted a woman in a North Side tavern after plying her with drinks until she fell from her chair and lost consciousness, prosecutors alleged Friday. The Chicago woman learned what happened after she asked the bar’s owner to review surveillance video when she returned to the bar to retrieve lost property.

Judge Susana Ortiz ordered Jose Callejas-Castillo, 30, to pay $15,000 toward bail and go on electronic monitoring.

“I find that Mr. Callejas was preying upon this particular individual and assisted with rendering her incapable of perhaps rebuffing or defending herself against his advances,” said Ortiz.

Jose Callejas-Castillo | Chicago Police Department

Chicago Police Department records show that the alleged attack occurred in the 5400 block of North Broadway, but authorities did not identify the establishment by name.

Prosecutors said the 25-year-old woman and a friend did not know Callejas, 30, when they sat down at the bar on the night of October 30. 

Callejas 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. At one point, the woman needed assistance after she fell from her chair.

Citing video footage, prosecutors said Callejas walked from behind the bar to help her, then hugged and kissed the woman and pulled down her shirt to expose her breast.

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

Later, Callejas texted his girlfriend, asking her to assist him with an inebriated customer. The girlfriend, who had been waiting outside to pick up Callejas, discovered the woman unconscious in the vestibule and learned her name and address from the woman’s “mumbled speech,” according to an assistant state’s attorney.

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

On Halloween morning, the victim awoke 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 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 has never been arrested before. His public defender said he has worked as a bartender and manager for nine years. The attorney argued that there was no evidence that he forced the woman to drink anything she did not want.

Prosecutors charged him with aggravated criminal sexual assault, aggravated criminal sexual abuse, and two counts of unlawful restraint. He will be in court again on January 18.

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CWBChicago was created in 2013 by five residents of Wrigleyville and Boystown who had grown disheartened with inaccurate information that was being provided at local Community Policing (CAPS) meetings. Our coverage area has expanded since then to cover Lincoln Park, River North, The Loop, Uptown, and other North Side Areas. But our mission remains unchanged: To provide original public safety reporting with better context and greater detail than mainstream media outlets. Our editorial email address is