CHICAGO — Many years before authorities charged Charles Oliver with five sexual assaults, at least four other women had accused him of tormenting them through violence, abuse or threatening behavior.
Oliver, 45, is awaiting trial in McHenry County, Ill., on charges he sexually assaulted five women in the span of 14 months dating to late 2011. Authorities have said there could be as many as 20 other victims.
Many of those pending cases involve prostitutes and escorts who advertised or responded to postings on Craigslist, but the earliest alerts about Oliver were sounded by an ex-girlfriend and a neighbor, court and police records show.
A common theme between the current cases and the earlier accusations was that Oliver allegedly threatened to kill the women or shame them by releasing videos of sex acts he recorded secretly or against their will, according to records.
One of the alleged victims in the most recent cases described being locked in a “sex dungeon” in Oliver’s basement, according to police records. She told police Oliver grabbed her by the neck, tried to tie her to a post and wielded a pry bar.
“I never thought I was going to get out,” the woman told the Chicago Tribune.
Nothing much happened to Oliver after any of the early instances, and he remained free until January. In one early case, he was given supervision after violating a court order. In another, charges were never pursued. No information is available on one case, while experts question the police response in another.
In 1994, an ex-girlfriend from McHenry alleged in a petition for an order of protection that Oliver was verbally abusive, “forced himself on” her and attacked her father with a bat.
Four years later, a neighbor in Round Lake filed for an order of protection after she rebuffed Oliver’s romantic advances. She accused him of vandalism, theft and a series of threats. The court found there was physical abuse and harassment.
In 2002, Oliver was arrested on a claim of criminal sexual assault in Cook County. That arrest was later wiped from his record, though, and it’s unclear whether he was ever charged.
And in 2008, a woman told Chicago police she was raped at gunpoint by a man who hired her as a prostitute. She picked Oliver out of a photo lineup, according to records. He was arrested in the case but never charged.
Oliver, of Woodstock, is now accused in multiple attacks that bear similarities to some of the earlier claims against him. Two of the women in the pending cases, speaking to the Tribune, described how the demeanor of the large, friendly man who picked them up abruptly changed, allegedly becoming violent and threatening.
Both women said they feared for their lives.
One, a petite 19-year-old, said Oliver responded to an ad she placed on Craigslist, picked her up in the near north suburbs and drove her to his Woodstock home.
She described how a towering man, more than twice her size, led her to the basement. She said he pulled out a gun, threw her to the floor and raped her. He then went through her phone, took photos of her and threatened to kill her if she contacted police, she said.
“I thought I was going to die,” she said recently, recounting the alleged attack from jail, where she was being held on charges related to a stolen vehicle.
The most recent alleged victim, the one who described a “sex dungeon” to police, said she and Oliver also met through a Craigslist ad. The basement room’s contents included a chair, an inflatable mattress and a pole with strings on each side that could be used to tie someone up, she said.
She said the basement door locked behind them, and when he finally agreed to let her out — only to go to his bedroom — Oliver allegedly used a special tool to open it.
Once in the bedroom, the woman alleged, Oliver choked her and forced her into the view of the video camera before sexually assaulting her. Though she said she fought back, at one point drawing blood when she scratched him, she said that only enraged him more.
Since that night, she said she is easily startled and tries to avoid going out after dark. “I still see his face,” she said.
The Tribune is not naming the women because they are alleged victims of sexual assault.
At least two of the women in the current cases against Oliver said he claimed to be a police officer, according to interviews and police reports. One woman told police the attacker showed her a case for a .45-caliber handgun and told her he was a well-connected officer whose friends would “cover for him if needed,” according to police records.
She, too, alleged she was choked and then sexually assaulted.
“You’ll listen to everything I say, or I’ll kill you,” the woman recalled him telling her, according to police reports.
More than a year passed before authorities in several jurisdictions were able to link the woman’s claims to similar, subsequent reports and then make an arrest.
That came in January, when Oliver was charged with sexually assaulting two women. Authorities have said that a search of his home then turned up a trove of evidence, including cellphones, driver’s licenses and thousands of images of women engaged in sex acts with him — some, prosecutors said, that appear consensual.
After he was released on bail, Oliver was taken into custody again in February and charged with three additional sexual assaults.
At that time, Oliver was also charged with harassment of a witness after his earlier release from jail. He is accused of threatening a family member of an alleged victim, saying he had been “watching” him and that he “still had videos,” according to court documents.
Oliver’s attorney did not respond to multiple requests for comment. Oliver’s father declined comment. He twice bailed out his son earlier this year before Oliver’s bond was raised to $3 million, according to court records.
The string of cases underscores the complexities of prosecuting sexual assaults, particularly when the alleged victims are working as prostitutes and might be worried about being exposed or facing arrest themselves if they report assaults.
Authorities said Oliver threatened to report some of his alleged victims as prostitutes if they went to police.
“I think he chose his victims very carefully,” said Woodstock Detective Sgt. Jeff Parsons, who said his department, which is leading the investigation, has four detectives working on the case.
But some rape experts question whether there were also missed opportunities that allowed Oliver to allegedly reoffend. They say nearly all rape cases are fraught with challenges but that women who work in the sex industry are exposed to unique risks. Some men believe if they are paying, they can force a prostitute to do what they want.
“Sex and rape are two different things,” Sharmili Majmudar, executive director of Chicago-based Rape Victim Advocates, said. “To say that the two are so similar as to be almost indistinguishable is very problematic.”
And when such victims do speak out, society sometimes questions their credibility, said Kaethe Morris Hoffer, legal director at Chicago Alliance Against Sexual Exploitation.
“Women in prostitution, they know better than most women know that them telling someone that they have been sexually assaulted will result in nothing — no sympathy, no belief and no institutional response against the perpetrator,” she said. “ … It’s easier to get away with victimizing someone who is already vulnerable.”
The sex worker who alleged that a man raped her at gunpoint in Chicago in March 2008, however, did report that the next day, according to police, and she was examined at an area hospital immediately afterward.
Oliver was arrested in January 2009 on suspicion of the sexual assault, police records show. But he did not match DNA from evidence taken from the victim, police said, and by that time they were unable to locate the woman.
“Not having a DNA match makes it extremely difficult to prosecute the case, therefore, we are unable to charge,” said Chicago police spokesman Adam Collins. “ … By law, without a positive DNA match and without a complaining witness, there are no grounds to hold someone.”
Police said they did not consult the state’s attorney’s office about whether to bring charges against Oliver at the time but said the case remains open. Two relatives of the woman who made the complaint in 2008 said authorities have been in contact with them since Oliver’s arrest this year.
Majmudar said the fact that almost 10 months passed between the woman’s 2008 report and Oliver’s 2009 arrest also may have contributed to the inability to locate her.
“That lag time alone can communicate to a survivor how important their case actually is,” Majmudar said.
As for the lack of a DNA match, some experts contend that’s not uncommon in rape cases and shouldn’t exclude a suspect on its own. There can be a number of explanations for a mismatch, including that the woman had consensual sex with another man.
“It all depends on the victim’s explanations for whatever she’s been doing,” said Rockne Harmon, a former prosecutor in California and national DNA expert. “When the DNA matches, that alone tells you that the DNA matches, but it depends on the context of the rest of the case. It’s exactly the same when the DNA doesn’t match.”
Steven Jansen, a former Detroit prosecutor and vice president of the Association of Prosecuting Attorneys, noted the considerable difficulties in prosecuting a case with neither DNA nor a locatable victim. But he warned that “sometimes that process can be self-fulfilling.”
“If you believe that you’re never going to get the charges past the state’s attorney’s office or the jury will never convict on this type of case, we’re not allowing the process to move forward, and you never will get the charges or let the jury hear the case,” he said.
The case a McHenry County jury will presumably hear against Oliver will present him in stark contrast to the man some neighbors and old high school acquaintances recalled. Neighbors described him as a nice guy who worked in his yard and would give them a slight wave. Former classmates at Niles West High School in Skokie described him as friendly and mild-mannered. All said they were shocked by his recent arrests.
At 20, Oliver fathered a child and soon after petitioned for custody, records show. The parents, who were not married, later agreed on joint custody, and the child ultimately moved out of state with her mother, according to court documents.
In 2002, Oliver filed for bankruptcy, court records show. He went on to manage his own company, Oliver Mechanical, but it was dissolved in 2008 for failure to file an annual report, according to records. When he was arrested in January, Oliver said in court documents he did not have a job but listed heating and air conditioning as his line of work.
Also in 2002, Oliver was arrested in Cook County for criminal sexual assault, according to McHenry County prosecutors and documents. That case, however, does not show up in his public criminal record. Arrests that do appear on a person’s record may have been expunged.
Years earlier, in 1994, a woman who had identified herself as Oliver’s ex-girlfriend filed for an order of protection against him. In a handwritten court petition, she detailed allegations that bear similarities to the current criminal complaint.
“He said he secretly videotaped us together, and he’d get pictures done and distribute them in the area to get back at myself and my father,” she wrote in 1994. “ … During our relationship, Charles was verbally abusive and forced himself on me.”
She alleged Oliver went after her father with a bat when he asked Oliver to leave. In court documents and a recent interview, the woman said she feared for her safety and that of her family.
Oliver was later charged with violating the order and harassment and was sentenced to court supervision, records show.
Another woman petitioned the court for an order of protection against Oliver a few years later, saying he first approached her about air conditioning when she moved across the courtyard from him in Round Lake.
“He seemed gentle enough, kind enough, like a big teddy bear type,” she said, and so she accepted when he asked to take her out on his boat.
She said in an interview that she began noticing red flags almost immediately. Only about two weeks after their first outing, she said, he told her he loved her and introduced her as his girlfriend. Soon after, he told her he was going to quit his job, move in with her and become a volunteer firefighter, and told her she could support them both, she said.
Her attempts to distance herself from Oliver led to heated arguments. In her petition for the protective order, she wrote that he said, “I was his enemy, he was going to make me regret not going out with him, I have turned this into a war that he will finish.”
She claims that Oliver hung a dead duck on her garage door, vandalized her air conditioning unit and paraded outside her house in his hunting suit with a shotgun over his shoulder.
“I changed my telephone number and have been staying at my parents off and on because I am afraid of him,” she wrote in her 1998 petition.
Her mother said they bought their daughter an alarm system for the house after the first incident.
“He wouldn’t take no for an answer,” she said.
Oliver is due in court on Friday. His trial date has not been set.
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