Secret grand jury proceedings in R. Kelly’s Chicago case were briefly made public

CHICAGO — A recent motion by attorneys for R. Kelly’s former business manager, Derrell McDavid, did more than just seek government reimbursement of McDavid’s legal fees — it also lifted the curtain on secretive grand jury proceedings that led to the bombshell indictment in the first place.

In making the unusual argument that prosecutors should be on the hook for $850,000 in the wake of McDavid’s acquittal, attorney Beau Brindley attached transcripts of grand jury meetings and testimony that were supposed to remain under wraps essentially forever.

The transcripts — which were public for several hours Tuesday before prosecutors asked the court clerk to seal them — detail a crucial February 2020 meeting of the special grand jury where prosecutors were seeking the return of a superseding indictment against Kelly, McDavid, and a third associate, Milton “June” Brown.

While grand jury proceedings sometimes come out in open court in snippets of transcripts to buttress other testimony or impeach a witness on the stand, the filings in the R. Kelly case offered a rare glimpse of how prosecutors go about securing an indictment in a high-profile case.

Here are some of the revelations in the filings:

—The grand jurors were wondering about something that later became a major issue in the trial: Where was the alleged tape at the heart of the conspiracy charges?

Near the beginning of the Feb. 13, 2020, session, a grand juror asked Assistant U.S. Attorney Angel Krull, who was heading up the investigation, “Has the missing porn tape ever showed up? There was like, a bunch.”

The reference was to what prosecutors called “Video 4,” a tape Kelly purportedly made at his home on West George Street in the late 1990s showing him having illegal sexual contact with his underage goddaughter and young woman, Lisa Van Allen.

Van Allen testified that she stole the tape from Kelly’s collection and sent it to her friend, Keith Murrell, in Kansas City, Mo. The conspiracy charges alleged Kelly’s legal team later hired another man, T-shirt merchandiser Charles Freeman, to get the tape back.

Krull told the grand jury panel the tape still “has not surfaced,” though four witnesses had testified to them about its existence and the alleged plot by Kelly’s team to get it back.

“I mean, the reason why we don’t have it is that you heard testimony about how Mr. Keith Murrell returned that tape to Mr. Kelly’s associates and was polygraphed and paid $100,000,” Krull said, according to the transcript. “So the reason we don’t have that tape is because it was returned to Mr. Kelly.”

The tape’s absence loomed large at trial, where defense attorneys questioned whether it existed at all, and characterized Van Allen, Murrell and Freeman as liars and extortionists.

The trial jury ultimately acquitted all three men of the conspiracy and obstruction counts.

—Prosecutors at one point showed grand jurors evidence about Kelly’s illegal marriage to his 15-year-old protegee Aaliyah.

As Krull presented the case to grand jurors, one of them asked why they weren’t charging Kelly with abusing Aaliyah.

“I don’t mean this in a disrespectful way or anything,” the juror said, according to the transcript. “When you first brought us evidence, you showed us the marriage license with him and Aaliyah ... so I was wondering why she wouldn’t be part of it if he married her when she was a minor and abused her?”

Kelly married Aaliyah in 1994, Krull explained, but the law under which they were charging Kelly — enticement of a minor to engage in sexual activity — didn’t exist until 1996. The marriage was quietly annulled, and the Aaliyah was killed in a plane crash in 2001.

Still unclear is why Chicago grand jurors were shown evidence related to Aaliyah if prosecutors ended up not charging him with any conduct related to her. During the trial, U.S District Judge Harry Leinenweber barred any mention their relationship, while defense attorneys were allowed to paint a picture of Aaliyah’s uncle, Barry Hankerson, as a vindictive control freak out to destroy Kelly’s career.

Kelly did face charges related to the illegal marriage at his 2021 trial in Brooklyn’s federal court, where jurors found Kelly guilty of a wide-ranging racketeering scheme. The judge in that case sentenced the singer in June to 30 years in prison.

—Prosecutors were hopeful that private investigator Jack Palladino would come in to testify or give a statement to the grand jury — but he was killed during a botched robbery outside his home in San Francisco.

At trial, Freeman told jurors a wildly memorable tale about how Palladino, a famous private eye based in California, was part of a scheme by McDavid and other Kelly associates to pay him up to a million dollars to hunt down Video 4, which he said had surfaced with some people in Atlanta.

Among the evidence backing up Freeman’s story was a written contract he and Palladino signed in August 2001 promising $100,000 plus expenses for Freeman if he recovered a “performance tape” of Kelly’s.

Krull told the grand jury in 2020 the contract had only recently been obtained after subpoenaing Palladino, who was also an attorney, and working through “all the special rules” that apply when an attorney is asked to turn over records.

Krull said they were still following up on leads from the documents and conducting interviews, and that the grand jury might hear more testimony about them in the future, including from Palladino himself.

“We are going through his records and determining whether whether or not he will come and sit for an interview, and if so then well determine whether he will come and testify,” Krull said, according to the transcript. “So that’s a possibility.”

But that apparently never happened. On Jan. 26, 2021, Palladino, 76, fell and hit his head on the sidewalk while tussling with would-be robbers outside his home in San Francisco’s Haight-Ashbury neighborhood and never regained consciousness. Two men were arrested and are awaiting trial on murder charges.

In the end, Palladino’s records may have actually turned out to be more of a help for the defense than a smoking gun for prosecutors.

At trial, McDavid’s attorneys were able to show the jury some of Palladino’s memos labeling Freeman’s contact with the team “Kelly extortion,” as well as other business records appearing to show the private eye traveled alone to Kansas City to meet with Freeman, contradicting Freeman’s testimony that McDavid was there too.

—Prosecutors learned only after indicting Kelly that one of his accusers was not actually underage during her first sexual encounter with the singer.

Van Allen, who was a key prosecution witness at the trial, told the federal grand jury in 2019 that she was 17 when she met Kelly at a music video shoot — the same claim she had made repeatedly in previous years, including as a prosecution witness in Kelly’s 2008 Cook County trial. She became “Minor 2″ in the initial Chicago federal indictment, which charged Kelly with abusing her.

But after that, Krull told jurors in 2020, a federal investigator tried to nail down the date of the video shoot. It was apparently the first time any authorities attempted to independently verify Van Allen’s age at the time she met Kelly. The person who owned the house where the video was shot still had records of the rental, which showed it was filmed just after Van Allen had turned 18, Krull told grand jurors.

So “Minor 2″ was dropped from the indictment, becoming instead “Individual D” — a cooperating witness. But Krull told the panel Van Allen “is very important still to the indictment with respect to the obstruction of justice allegations.”

Van Allen testified at length during Kelly’s trial, saying she had been mistaken when she said she was 17. Defense attorneys seized on the discrepancy to paint her as a liar and opportunist. In the end, jurors acquitted Kelly and his co-defendants on the charges related to Van Allen’s testimony.

—The minor victim who was added to the superseding indictment had told the grand jury Kelly first sexually abused her in New York. But that never came out at trial.

At the grand jury meeting, Krull said they were adding a new victim to the charges who was a schoolmate of Kelly’s goddaughter and was also alleged to have been sexually abused by the singer multiple times when she was a minor.

“One of them in particular, the very first one, happened on a trip to New York City that she described an encounter happened in New York City at a hotel there,” Krull said in her presentation to the grand jury. “Then she described many other encounters with Mr. Kelly, all happening when she was under 18. And so because of that we are adding her to the indictment.”

Krull said the abuse continued after the victim, who at trial went by the pseudonym “Brittany,” became legally an adult, “but for purposes of this charge we’re only focusing on the conduct that happened to her when she was under 18.”

At trial, prosecutors promised jurors that they’d hear directly from Brittany. But she was never called as a witness for reasons unexplained.

Instead, jurors were asked to rely on testimony from other witnesses, including Jane, who said Kelly engaged her in threesomes with Brittany between five and 10 times. Another victim, Pauline, told the jury that Kelly also had threesomes with her and Brittany when Pauline was 15 or 16, and said Brittany is about a year older than her.

Pauline said that when she was 20, she called Kelly’s business posing as Brittany and threatened to go public about some wrongdoing if he didn’t give her money.

“Well, he called it extortion,” Pauline told the jury. “I called it ‘don’t play with me.’"

But Brittany’s absence did not go unnoticed by the jury, which acquitted Kelly of the enticement counts related to her accusations.

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