Man Tasked to Recover R. Kelly Sex Tapes Slammed During Cross Examination

Chicago, IL — Charles Freeman claimed R. Kelly and his team made a verbal agreement to pay him $1 million to secure videos of the singer allegedly sexually assaulting a minor during his testimony on Tuesday and detailed a timeline and plan on how he claimed he did so during R. Kelly’s federal child pornography trial in Chicago at Dirksen U.S. courthouse. On Wednesday, the defense took Freeman to task on his claims for their cross-examination.

On Day Eight, attorneys for Kelly and his co-defendants — former business associates Derrel McDavid and Milton Brown — launched their day-long cross examination of Freeman, which was contentious, though the parties occasionally found humor amid the serious proceedings. Kelly’s lawyer Jennifer Bonjean and McDavid’s attorney Beau Brindley each said Freeman received immunity in exchange for his testimony, which at times contradicted his versions of events he had previously recalled in front of a Cook County grand jury and in an affidavit for a federal grand jury.

An animated Brindley was up first in the cross examination, and he honed in on Freeman’s 2019 testimony, where Freeman didn’t mention McDavid being present during meetings concerning obtaining the videotapes. Brindley contrasted that with Freeman’s current testimony at the ongoing trial, where Freeman added McDavid in places he previously said he wasn’t in attendance.

Early on, Freeman appeared amused by the proceedings. “Is this funny? You having a good time?” Brindley asked Freeman, who leaned back with a smile and said, “Yes, I am.” Freeman smiled as both Brindley and later Bonjean confronted him on the apparent conflicting testimony he has given under oath at the current federal trial and previously at a Cook County grand jury and federal grand jury. But by day’s end, he appeared more defensive, reiterating that what he testified in front of previous grand juries were a “summary” that didn’t tell the full story.

Among the alleged discrepancies the defense pressed Freeman on was when he first learned about the location of the tape and who informed him of it, how many tapes he found, when and what he discovered was on the tape, and who first allegedly hired him to recover said tapes.

While Bonjean questioned Freeman about the monetary deal he claims Kelly and his associates cut with him to retrieve the tapes, Freeman said he and R. Kelly had been friends since 1991 and that Kelly knew he could make it happen, “just like he hired you to get the job done,” Freeman said. Bonjean quipped back, “I don’t break the law to get the job done. That’s the difference between you and me.”

On Tuesday, Freeman said Kelly called him around 2001 to recover tapes that depicted Kelly allegedly engaging in sexual acts with a minor. He said that he then heard from McDavid, as well as the infamous private investigator Jack Palladino, both of whom allegedly told Freeman he would get a “reward” if he retrieved the video (Palladino, who worked for Kelly, as well as Bill Clinton and Harvey Weinstein, died after being attacked last February.) Freeman claimed he did not know what was on the tape at the time, stating only that McDavid described it as a “performance tape,” and that if Freeman got it back, “they would take care of me.”

In August 2001, Freeman signed a contract saying he’d get $100,000, plus expenses, if he recovered the tape. On Wednesday, the defense shared a copy of the contract on a screen in the courtroom, which Freeman confirmed he signed. He also testified that McDavid told him he could earn $1 million for the job. On Wednesday, the defense pointed out that there was no contract or evidence to back that $1 million was ever on the table, and further used Freeman’s claim to illustrate that he appeared to be a liar and an extortionist. The defense brought up two lawsuits Freeman filed against Kelly, with McDavid named as a co-defendant in one. The suits were settled. He was also grilled about his plans to hold a press conference around the time of Kelly’s 2008 trial, but he later canceled it after he said McDavid gave him another $150,000.

Freeman testified that he still had copies of the tape as recently as 2019, and only turned them over to the authorities, via his lawyer, after he learned the police were looking into him in connection to Kelly. Asked on Tuesday why he didn’t immediately turn the tape over to the cops after getting it in 2001, Freeman replied, “Because the police wasn’t going to pay me a million dollars.”

Brown’s attorney, Mary Judge, also briefly cross-examined Freeman on Wednesday, simply asking if her client had been named in any of Freeman’s lawsuits as Freeman had claimed previously. “I never sued Milton Brown,” Freeman said.

Prosecutor Jeannice Appenteng redirected by emphasizing that Freeman’s previous grand jury testimony contained summaries of events, and she had Freeman reiterate who hired him to retrieve the tapes: He responded McDavid and Palladino.

Kelly is facing multiple charges of coercing five minors into sex acts, and several charges related to producing child pornography. He and co-defendants McDavid and Brown are also charged with receiving child pornography as part of an alleged effort to recover missing tapes that allegedly show Kelly engaged in sex acts with minors. Additionally, Kelly and McDavid are facing obstruction of justice charges tied to allegations that they paid off people who knew about Kelly’s alleged abuse and tried to impede the 2008 child pornography investigation into Kelly. All three men have pleaded not guilty. 

On Wednesday, Appenteng told Judge Harry Leinenweber that the prosecution’s case could wrap as soon as the middle of next week. The trial, which began last week, is slated to conclude within a month, with testimony from more alleged underage victims expected in the coming days.