‘Is this funny?’: Defense attorneys in R. Kelly trial tear into prosecution witness who smiles back

From the very start of his combative, contentious cross-examination Wednesday in the latest federal trial of R&B superstar R. Kelly, Charles Freeman simply looked amused.

Defense attorney Beau Brindley kicked off the interrogation, asking whether Freeman found it difficult to trust the word of a man who lies, who cheats, who steals and who takes advantage of people for money.

It didn’t rattle Freeman. He just kept on grinning at Brindley, a lawyer for one of Kelly’s co-defendants. Finally, Brindley demanded, “is this funny? Are you having a good time?”

“Yes, I am,” Freeman said.

So it went as Brindley, and then his fellow defense attorneys, got the chance to tear into the man they’d already described to jurors as an extortionist and a criminal. Freeman told the jury earlier this week that he spent the early 2000s trying to hunt down videos for Kelly and Brindley’s client, Derrel McDavid, in exchange for large cash payments.

The videos allegedly depicted Kelly sexually abusing a 14-year-old girl in the 1990s as Kelly rose to stardom.

Throughout the day-long cross-examination of Freeman on Wednesday, Brindley mocked the idea that Kelly’s top-tier private investigator, Jack Palladino, would hire “a T-shirt salesman” to track down sensitive videos. Freeman had done merchandising for Kelly and others.

At one point, Brindley asked Freeman whether he had a “hearing problem.” Freeman countered that Brindley had a “reading problem.”

Freeman acknowledged that, after he recovered a tape in 2001 that allegedly depicted Kelly sexually abusing a 14-year-old girl, he intended to give a copy to a friend. The friend’s girlfriend didn’t let him keep it, he said.

Then, when Kelly attorney Jennifer Bonjean had her shot to question Freeman, she tried to tick through all the crimes Freeman could have been charged with had he not secured an immunity deal. They included buying or selling child pornography, extortion and soliciting bribes. The feds objected, and U.S. District Judge Harry Leinenweber finally cut Bonjean off.

“It would take me too long to go through them all,” Bonjean quipped. The comment seemed to prompt laughter among some of the jurors.

Still, Freeman insisted to Brindley that, “I never tried to get money for doing something bad.”

“I was helping a friend,” he said.

At one point Wednesday, Freeman mentioned the late singer Aaliyah Haughton, who Kelly married when she was 15 and he was 27. Kelly’s sexual abuse of Aaliyah is part of his 2021 conviction in Brooklyn’s federal court, for which he is already serving a 30-year prison sentence. It’s not part of Kelly’s latest trial, though, and Leinenweber wound up telling jurors to ignore the comment.

In this trial, Kelly is facing charges alleging child pornography, obstruction of justice and the enticement of minors into criminal sexual activity.

Brindley on Wednesday frequently brought up the name of one of Freeman’s attorneys — Michael Avenatti — who is now in federal prison for extortion and stealing from a client.

Dressed in a black pinstripe suit during his animated questioning, Brindley repeatedly pointed to Freeman’s previous comments to grand jurors in federal and state court, which often tended to conflict with his testimony Tuesday.

Freeman told jurors Tuesday that he was hired by McDavid and Palladino in 2001 to track down a tape for Kelly. He said he signed a contract with Palladino to recover the tape for $100,000 plus $40,000 in expenses. Then, he said he went to a home in Georgia and demanded that a woman who answered the door there give him the “mother f---ing tapes that ya’ll stole from Robert Kelly.”

Brindley painted Freeman as being all over the map in his various statements to law enforcement. He suggested Freeman had been inconsistent about where he found the tape in the Georgia home, when he learned what was on the tape, who told him where to find it and when he actually put his hands on it.

Freeman accused Brindley of “jumping all around” in the timeline and misconstruing his previous comments.

Brindley at one point showed Freeman paperwork from a polygraph expert, suggesting that Freeman had taken a lie-detector test the same day he delivered a tape to Palladino. Freeman said he’d never seen the paperwork before.

“So you say,” Brindley said.

Brindley insisted that Freeman never actually went to Georgia to hunt down the videotape, but rather took advantage of Kelly sex tapes sold on the street to shake Kelly down. Brindley called Freeman’s story “ridiculous” and accused Freeman of changing his story to add McDavid to the conspiracy.

“Do you recognize a pattern here?” Brindley asked.