Natalee Holloway's confessed killer caught trying to extort $250K from grieving mother in FBI sting video

Joran van der Sloot spent years tormenting Natalee Holloway's family with a tangled web of lies. But behind closed doors, the convicted killer was playing an even more sinister game.

Now, previously unseen video from an FBI sting reveals just how far he was willing to go to exploit a grieving mother's desperate search for answers. The Netflix true crime docuseries "Taken: Natalee Holloway," co-directed by Dani Sloane and Matthew Galkin, features video of the 2010 sting operation showing the Dutch national attempting to extort money from Holloway's family.

"His brazenness stood out to me, the fact that he's sitting across from lawyer John Q. Kelly, and he's going 'Can I have a soda? It's so hot outside, I had to wait for a cab,'" Sloane told Fox News Digital. "He's having a casual conversation while he's extorting the mother of his victim for money, for information that only he knows. It's astonishing. You really don't often get to look at a perpetrator like that. He feels really cavalier and he's just casual about the whole thing."

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"It’s pretty haunting to see," Sloane added.

Holloway, 18, disappeared on May 30, 2005, while she was on a graduation trip in Aruba with her high school classmates. She was last seen leaving a bar with van der Sloot, a student at an international school on the Caribbean island where he grew up.

Van der Sloot, long suspected in connection with her disappearance, was never charged with her murder. A judge declared Holloway dead in 2012, but her body was never found.

Nearly five years after Holloway's disappearance, van der Sloot emailed Kelly, an attorney for Holloway's mother, Beth Holloway, the film revealed. For $250,000, he offered to provide information about Holloway's death and the whereabouts of her remains.

Kelly and van der Sloot agreed to meet at a hotel in Aruba in May 2010, where Kelly would hand over a $25,000 deposit in exchange for the information, starting with $10,000 in cash. By then, according to the documentary, van der Sloot had changed his story about what happened to the Alabama teen roughly 40 times.

"Joran went on TV countless times and continued to tell slightly different fabricated stories," Sloane said.

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"I think it's probably an even higher number than that. We did our own approximations and it's a pretty staggering number of different stories he told, even just small details he changed within the storytelling about what happened that night. It's astonishing. I've been doing this for a really long time, but I personally have never seen anything like this where it's very clear who did this."

"He is so masterful at evading law enforcement and evading consequences by just outright lying," Sloane added.

According to the film, Beth agreed to give van der Sloot $25,000 because she believed it was her chance to finally learn what happened to her daughter from the man she had long suspected of killing her. She was on standby at an Alabama bank, ready to wire the remaining $15,000 as soon as van der Sloot signed their agreement.

Beth subsequently wired the remaining $15,000 to van der Sloot's bank account, bringing the initial payment to $25,000.

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Before the meeting, Kelly had contacted the FBI, which worked with police in Aruba to secretly record the exchange in hopes of building a criminal case against van der Sloot.

The previously unreleased video of the exchange shows Kelly handing over $10,000.

"To be completely honest, for me, the biggest deal is the 225 afterwards," van der Sloot tells Kelly in the recording. "Did you put in the contract that that would be paid within a month?"

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Kelly said yes and van der Sloot signed the agreement.

In the docuseries, Kelly explained that van der Sloot was never going to receive the remaining $225,000.

"If he disclosed Natalee's whereabouts then he was going to be arrested for it," Kelly explained. "And if he didn't disclose what happened to Natalee, he was going to get arrested anyway for extortion or fraud."

Van der Sloot then took Kelly to a nearby house, claiming Holloway's body had been buried in the foundation while the home was under construction.

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"It's honestly a horrific thing to watch," Sloane said. "Just to see how that conversation played out is really stunning."

Investigators determined the information was false. But before U.S. authorities could file charges against van der Sloot, he left Aruba for Peru.

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Van der Sloot's trail of lies was about to take an even deadlier turn. On May 30, 2010, exactly five years after Holloway's disappearance, van der Sloot murdered 21-year-old Stephany Flores Ramírez in his hotel room in Lima, Peru.

According to the film, van der Sloot told investigators he attacked Flores Ramírez after she discovered information about Holloway's disappearance on his laptop. He beat and strangled her.

In July 2014, van der Sloot married Leidy Figueroa, a Peruvian woman. They later had a daughter.

In the film, retired FBI special agent Alexandra Montilla recalled an encounter in which the "charismatic" van der Sloot told her about a pet rabbit he shared with his daughter. According to Montilla's account, the rabbit scratched his daughter while she was petting it. Montilla said van der Sloot told her that he grabbed the animal and "ripped his head off."

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"I've dealt with a lot of criminals and, as a female, I thought this is probably one of the most dangerous ones," Montilla said.

Sloane said Montilla still vividly remembers the encounter.

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"It really lives in her memory," Sloane said. "It's something that stands out to her out of all the offenders and perpetrators she has spent time with. It counts a lot when a seasoned member of the FBI is horrified by something."

In June 2023, van der Sloot was temporarily transferred from Peru to the United States to face federal extortion and wire fraud charges stemming from his 2010 scheme targeting Beth. On Oct. 18, 2023, he pleaded guilty to both charges in federal court in Alabama and was sentenced to 20 years in prison, to be served concurrently with his Peruvian prison sentence.

If van der Sloot is released from prison in Peru before completing his U.S. sentence, he would serve the remaining time in the United States.

As part of his plea agreement, van der Sloot also confessed to killing Holloway in 2005. The convicted killer said he struck her in the head with a cinder block after she rejected his sexual advances, then disposed of her body in the ocean. This time, Beth said she believed he was telling the truth.

"This case was difficult to solve," Sloane said. "There were no forensics to speak of. Natalee’s remains were never found and have never been found to this day. All of this hinged on dealing with Joran. It was incredibly difficult for anyone that was interrogating him to pin him down. He was good at spinning a story. This was someone who told years of stories, one more outlandish than the next about what happened to Natalee."

Beth spent nearly two decades seeking answers about her daughter's disappearance and now advocates for other families of missing people. Sloane said that while Beth finally has answers about Holloway's death, she continues to live with the loss of her daughter every day.

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"I think Natalee would be proud of all of us," Beth says in the film. "I think Joran tangled with the wrong girl."

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