Natalee Holloway’s Brother Details Gut-Wrenching Days After Her Murder

Natalee Holloway’s Harrowing Final Moments Detailed

Nearly 20 years later, Natalee Holloway’s brother still has a crystal-clear memory of the harrowing days following her 2005 disappearance.

In E! News’ exclusive sneak peek at Peacock’s new documentary Pathological: The Lies of Joran van der Sloot, Matthew Holloway recounts searching for her body in Aruba in the wake of her murder at the hands of Joran van der Sloot.

“I remember my dad jumping down into a landfill and just physically ripping open trash bags,” Matthew details in the somber preview. “Moving large appliances, picking up stuff with his bare hands, and just searching for Natalee’s body. Dad was in that 100 percent and seeing that was really powerful.”

However, Natalee’s body was never found.

“I had a gut feeling that, just as a parent, you have that feeling that she’s not here anymore,” her father Dave Holloway remembers in archival footage. “But on the other hand, I had to convince everybody else that I had the wrong feelings. That maybe we would find her alive. But I had a sinking feeling that things aren’t right.”

Pathological will examine Joran’s lifelong pattern of violence and pathological lying that led to him brutally murdering Natalee and, in 2010, a 21-year-old Peruvian named Stephany Flores several years later in 2010. 

In addition to Matthew’s first-hand account of his sister’s death, the true crime doc will feature, according to Peacock, “rare interviews with victims’ family members, eyewitnesses and experts on the criminal mind.”

The doc comes just months after Joran was sentenced in October to 20 years in prison for extorting Natalee’s mom Beth Holloway after promising information about the her death and the whereabouts of her remains in exchange for $250,000. He later confessed to killing the 18-year-old, though the statute of limitations in Aruba is only 12 years.

Peacock/Holloway Family/FBI

Before being extradited to the U.S. to face the new charges, the now-36-year-old was serving a 28-year sentence in Peru for Stephany’s murder.

Pathological: The Lies of Joran van der Sloot debuts Tuesday, Feb. 27 on Peacock.

For a breakdown of Holloway’s tragic case, keep reading.

Holloway Family

Seven Arrests, No Charges

When Aruban authorities first questioned Joran van der Sloot and brothers Deepak and Satish Kalpoe, they said they took Natalee Holloway to California Lighthouse, near Arashi Beach on the northwest tip of the island, to shark-watch, then dropped her off at her hotel at around 2 a.m., the morning of May 30, 2005.

Two former hotel security guards were arrested on June 5 after Joran and the Kalpoes claimed they saw a guard approaching Natalee outside her hotel before they drove off. The young men were arrested on June 9 and held on possible charges of first- or second-degree murder and kidnapping resulting in death. Aruban Attorney General Caren Janssen explained that they had been hoping that one of them would lead police to definitive evidence and that’s why they weren’t taken into custody right away. 

The beach was searched on June 14, and Joran’s house was searched the next day, where investigators seized two vehicles, computers and cameras. “You have to build up an investigation. You can’t just go in there like a cowboy,” Janssen told reporters in explaining the perceived delay.

The guards were released June 18, and one told police that a Kalpoe brother had told him while they were both locked up that they hadn’t taken Natalee to the hotel, but rather he and his brother had left her with Joran at a beach near the hotel. 

Police also questioned Paulus van der Sloot, Joran’s father, and arrested him on June 22. Multiple reports also noted the arrest of Steve Gregory Croes, a party boat DJ, in connection with the case; both Croes and the elder van der Sloot were released on June 26.

Satish Kalpoe admitted to lying to police at first; he changed his story to say he and Deepak dropped both Joran and Natalee off at the hotel and that was the last they saw of them. Meanwhile, a gardener at the Aruba Racquet Club gave police a sworn statement that he saw all three men in a car near the club at around 2:30 a.m., when the Kalpoes claimed they were already home.

Aruban police, Dutch marines, FBI agents and thousands of locals combed the area, but that was on land. Ultimately a volunteer group dispatched divers and sonar equipment on June 25.

Six weeks after she vanished, the family’s offered reward for Natalee’s safe return was $200,000, and the reward for information that could help lead to the truth was $100,000. By the end of July, the reward was up to $1 million if Natalee came home alive.

AP Photo/Courtesy of Beth Twitty

Parents’ Worst Nightmare

Upon arrival on Aruba, Beth Holloway went to the Holiday Inn to ask questions about a guy named Joran van der Sloot, who some of Natalee’s friends had met. When the night manager knew right away who that was, Beth asked to see casino security footage and then called police. Everyone went to Joran’s house, where his dad Paul kept close watch as authorities questioned his son.

With Beth and a growing number of interested parties along, Joran guided authorities back to the hotel to illustrate where he dropped Natalee off, and claimed that she fell and hit her head getting out of the car.

Dave Holloway remembered to Dateline being assured by a cop that sometimes tourists just missed their flights, and his daughter would probably turn up in a few days.

When Joran and the Kalpoes were arrested, Dave and Beth felt that had to be case closed, but that obviously turned out not to be true. Furthermore, as days and then weeks went by, it stated to sink in that Natalee in all likelihood wasn’t coming home.

Beth stayed in Aruba for two months, leaving a few weeks before the Kalpoes, who had been released on July 4, were arrested again on Aug. 26. The brothers and Joran were all released Sept. 3.

Divers from the Aruba Search and Rescue Foundation searched again in late August after getting a tip that a radar machine had detected human bones about a mile off the coast, but they came up empty.

In 2008, Beth told Dateline, “I mean, I’ve had calls since, you know, I couldn’t even— just—you know? I’m… from ‘Natalee’s in a freezer at the van der Sloot house’ to ‘Natalee’s in a boat in Venezuela or Colombia.’ It was hell at first.”

AP Photo/Rob Carr

No Longer a Rescue

In March 2006, 10 months after Natalee disappeared, Aruban authorities said witnesses had told them the teen was drinking heavily that night and had drugs in her possession, though no one said they saw her taking any of them.

“We feel strongly that she probably went into shock or something happened to her system with all the alcohol—maybe on top of that, other drugs, which either she took or they gave her— and that she… just collapsed,” Gerald Dompig, deputy chief of police for Aruba, told 48 Hours Mystery.

Believing her to be dead, they were searching the beach where Joran claimed he last saw her, as well as a salt pond near her hotel, for forensic evidence.

All the while, Joran’s story kept changing.

AP Photo/Pedro Famous Diaz

No. 1 Suspect

Joran, born in the Netherlands, was an honors student and athlete at the International School of Aruba. His attorney father was in the process of becoming a judge on the island when Natalee disappeared. According to her friends, she first met Joran at the Excelsior Casino in their hotel.

“He just looks like an average, normal high school guy,” Natalee’s friend and classmate Laraine Watson told Dateline in 2008. “I mean, I remember he’s really tall. I remember looking at him thinking, ‘Oh, who’s that guy?’ You know, he’s hanging out with my friends.” She added, “I wasn’t really suspicious. I mean, he’s going to come out with us later.” Watson said she didn’t remember seeing him have any interaction with Natalee that night.

Laraine didn’t see them leave together, but other classmates did. “They didn’t think anything of it at the time, but she had gone off with Joran and some of his friends,” she recalled. 

Right away, Joran was readily identified by a Holiday Inn staffer as a regular known for going after young female tourists. He spent three months in jail and was released without any charges being filed, a judge having ruled there wasn’t enough evidence to hold him any longer.

Toward the end of 2007, he and the Kalpoe brothers were re-arrested, but again, nothing came of it and they were all released. 

Joran proceeded to freely travel the world, living in Thailand for a few months, acting suspicious. He reportedly talked about the case all the time, seemingly pleased that it had made him famous, but his temper was easily triggered. Sitting for an interview with Dutch crime reporter Peter de Vries in January 2008, he threw a glass of wine in Peter’s face when the reporter questioned why people should believe anything he said. 

AP Photo/Leslie Mazoch

More Witnesses, More Confessions

Even more dramatically, however, the journalist engineered a hidden-camera sting that captured Joran telling Patrick van der Eem—who said he was paid $35,000 for his role in the operation—that he’d been on the beach with Natalee, they’d had sex, and then right after she suddenly started shaking and lost consciousness.

“All of a sudden, what she did was like in a movie,” he said in the clip, which aired on RTL Boulevard in February 2008. “She was shaking, it was awful… I prodded her, there was nothing.” So, he claimed, he had a friend take her out on a boat to dispose of her body. “He went out to sea and then he threw her out, like an old rag.”

In a tease for the episode, Peter promised, “The mystery of Natalee Holloway will be solved Sunday.” 

However, Joran’s attorney objected: “They act quite frankly like clowns. If they have a resolution, they should bring a case and stop talking about cryptic information.”

Joran, then living in the Netherlands again, phoned into another Dutch program, Pauw & Witteman, to say that what he told Patrick wasn’t true. “That is what he wanted to hear, so I told him what he wanted to hear.”

In November 2008, CNN reported that Aruban authorities had two new leads to follow. First, a witness had come forward who could place Paul van der Sloot—who had told police he was home asleep until 7 a.m. on the night in question—and his son near a pond on the island at 4 a.m. on May 30, 2005. The witness said a young man, wet from the waist down and wearing only one shoe, was running from the pond toward a fast-food restaurant. Then the witness said the young man and an older one drove by in a red Jeep about 10 minutes later.

The other tip came from Joran’s former girlfriend, who told police Joran had said to her one night, “‘Who knows? You may now be on the beach with someone who is able to get rid of a corpse?'”

Aruba’s chief prosecutor, Hans Mos, told CNN he considered what Joran said on the hidden camera to be a confession, and they were taking all of the new evidence into consideration as they determined their next step. 

NBC

More False Leads

The family hired a private investigator, Tim Miller, who spent almost a year knocking on doors and searching for Natalee in Aruba, sometimes with Dave Holloway. On Oct. 21, 2005, Natalee’s birthday, they had been in Aruba literally digging in a garbage dump when the deputy police chief told them he had a hunch that they needed to take their search to the sea. A fisherman’s hut had been broken into and among the items missing were a fish trap and tools that could have been used to weigh a body down.

Entrepreneur Louis Schaefer, who had been following the case, volunteered to finance an expedition to search the ocean floor within a certain radius. A boat named Persistence set off for Aruba in November 2007. On Dec. 24, they came across what appeared to be a fishing trap about 90 feet below the surface, and on Dec. 29 sent a remote-operated vehicle down to investigate. They spied what looked, to them, like a skull.

On Dec. 30, a diver from the boat joined two Aruban police divers. They did not find anything having to do with Natalee. “That’s probably about the time that—the chest pains intensified to an extreme. I mean, how many times can I take this?” Dave recalled.

Then, in early 2008, a person who identified himself as Marcos sent Dave a message, claiming he knew that drug runners had been paid to get rid of Natalee’s body at sea and instead took the remains with them to Nicaragua and hid them on land.

Miller went to Nicaragua and met with Marcos, who offered to go to the hiding place with a GPS tracker and look for the remains. As reported on Dateline, Marcos called Miller, claiming to have found her. 

“He says that she was wrapped in a blanket and her body fell apart,” Miller told NBC News. “He said, ‘but we had to put her in two ice chests.’ And he actually said, ‘call Mr. Holloway right now and tell him I’ve got Natalee.'” Miller did not call, not wanting to instill Dave with more false hope.

Marcos subsequently disappeared, never to be heard from again.

AP Photo/Pablo Martinez Monsivais

Alleged Extortion and a Seeming Gotcha Moment

Paul van der Sloot died suddenly of a heart attack in February 2010, leaving his son adrift. According to Holloway family attorney John Kelly, a desperate Joran emailed him that March, writing, as Kelly told Dateline, “‘I want to come clean. My father’s dead now. I have nothing to hide. I want to help Natalee’s family, but at a price, you know, for a quarter million dollars…I will tell you what happened to Natalee, where she is now so you can help Beth bring her home.'”

With Beth’s permission, John Kelly met with Joran in Aruba, promising to start with $25,000. The young man said he knew where the body was; John asked what would happen if they didn’t pay him. Joran allegedly replied, “‘Beth can wait another five years.'” The family then turned to the FBI, which helped orchestrate a plan to make Joran think he’d be getting paid in order to catch him committing wire fraud, which would at least be something to hold him on.

John and Joran met again, and this time John wired him a total of $25,000. In turn, Joran led John to a house near the Aruba Racquet Club, where he claimed he had stashed Natalee’s remains in what was then a freshly poured foundation, before the house was built. John said on Dateline that Joran claimed he had been on the beach with Natalee, he wanted to go, she resisted, and then he “got angry and actually threw her. He actually made the gesture in the car, on video, showing me how he threw her in anger, because she wouldn’t leave at that point. And according to him, she hit the back of her head, lots of blood and she was dead.”

John said he was skeptical of Joran’s overall story, which was that he first hid Natalee’s body at the beach with his father’s help, and then the next day they buried her. But he still hoped they had shaken something loose.

“When I got on the plane May 11 [2010], I thought it was a done deal,” John said. “And he was going to be arrested at some point. That he’d be talking at some point, and we’d get some closure at some point.”

But the house Joran pointed to hadn’t been under construction in 2010, according to the authorities who said they didn’t find his story credible enough to make an arrest.

John said that Joran remained in touch with him up until May 25, claiming he would turn himself in. Instead, he flew to Peru.

A federal grand jury indicted him on charges of wire fraud and extortion on June 30, 2010.

AP Photo/Karel Navarro

Stephany Flores Is Murdered

Joran approached 21-year-old college student Stephany Flores at the Atlantic City casino in Lima, Peru. As seen on security footage from various locations, they played poker for about two hours, then Stephany cashed in some chips and went with Joran to Hotel Tac, where he picked up his key from the desk. At 5:33 a.m. they went upstairs and disappeared together into room 309.

At 8:36 a.m. on May 30, 2010, five years after Natalee disappeared, Joran, apparently locked out, called the front desk to be let into his room. He left by himself 20 minutes later, carrying a backpack. The TV in his room was turned up and, according to Dateline, he told the clerk at the desk, “Don’t disturb my girl,” before he went out.

Two days later, Stephany’s badly beaten body was found in room 309. Her neck was broken.

Her parents had reported her missing. Ricardo Flores, Stephany’s father, was a prominent businessman and former race car driver, so the case was doubly sensational to the local media.

Joran fled south and was ultimately arrested in Chile. He at first insisted he was innocent, but then confessed to Stephany’s murder four days after his arrest, Lima police told the press. In fact, police said, he told them that he left Stephany briefly alone in the room and, when he returned, she was looking at his laptop and had found information linking him to Natalee’s disappearance, after which he killed her in a rage. Police also stated he told them he knew where Natalee’s remains were, but he would only tell Aruban authorities. “How could this happen?” Beth Holloway reportedly said when informed of Stephany’s death.

In addition to being charged with first-degree murder and robbery in Peru, the U.S. Attorney’s office in Birmingham, Ala., charged Joran with wire fraud and extortion.

His attorney argued the crime was manslaughter, but Joran ultimately pleaded guilty to murder, claiming he was suffering from “extreme psychological trauma” from the Natalee investigation, and was sentenced in 2012 to 28 1/2 years in prison. 

NBC

Face to Face

Beth Holloway went to Peru to visit Joran in prison in September 2010 with a Dutch documentary crew in tow, five years after seeing him the first night after Natalee had gone missing. “Leading up to May of 2010, that’s when all the extortion was going on with Joran,” she recalled to B-Metro magazine in 2015. “So at that point, I was not in a good place, so to speak.”

She recalled, “I think once I visited Castro Castro, Joran in prison, and was able to walk away from there, it was almost a freeing experience for me to know that it was time now. Joran was in prison, and this is what I had worked so hard for, for five years. This was what I had wanted in ’05.”

He didn’t provide answers, but Beth considered that moment a turning point all the same.

“It allowed me then to move onward….” she said. “I hadn’t found peace and joy and happiness yet—but I began to recognize it and learned how to embrace it, and then I think it just led to place where I am now, which is a good place.”

Further looking back on the prison visit, Beth said on Dr. Oz in 2017 that she didn’t expect “the empowerment that I would feel when I stood up from him and left him in prison… I almost saw him as this pathetic person, so I didn’t feel any hate. I saw him as so pathetic.”

Dave Holloway told AL.com in 2015 that he might go to Peru one day to talk to Joran. “I still hold out hope that with hard prison life, maybe he’ll change,” he said. “I don’t think at this point and time he’s ready to do anything, but we’ll probably one day make a trip to Peru.”

ERNESTO BENAVIDES/AFP/GettyImages

Behind Bars

Before agreeing to plead guilty, Joran said he was intimidated into confessing to killing Stephany, and that Peruvian authorities promised him he’d be extradited to the Netherlands if he cooperated.

In September 2010, Dutch newspaper De Telegraaf quoted Joran saying (per CBS News) about the extortion allegations, “I wanted to get back at Natalee’s family—her parents have been making my life tough for five years. When they offered to pay for the girl’s location, I thought: ‘Why not?'”

In July 2014, Joran was set to marry his pregnant Peruvian girlfriend, Leidy Figueroa, who told CBS News’ Crimesider that she met him in 2010 when she went with her cousin to visit another inmate. Conjugal visits were allowed at Piedras Gordas, the maximum-security prison north of Lima where he spent the first few years of his sentence after being transferred from Miguel Castro Castro.

According to Leidy, her future husband had transformed “into a new person.”

That August, however, Joran was transferred to the more remote Challapalca in the Andes mountains, where conditions are reputedly rougher, after allegedly threatening to kill the warden at Piedras Gordas. Leidy, who gave birth to a daughter in September, told Dutch newsgroup RTL that November that Joran had been stabbed by a fellow inmate at Challapalca—but the director of Peru’s National Penitentiary Institute denied it, calling her a compulsive liar in an interview with Peru news network Channel N.

In 2015, Leidy gave Fox News Latino a letter Joran wrote her from prison, in which he alleged that Stephany’s father had put a $10,000 bounty on his head. “I don’t want to die,” he wrote, entreating authorities to take action to secure his safety behind bars.

“Joran is a pathological liar who will say anything to better his condition and get what he wants,” Ricardo Flores said in a statement to Fox News Latino, per People. “Now that he can’t get his way, he will say or do anything to get attention and get transferred to an easier location.” 

Mark Wilson/Getty Images

Instead, a Confession

In his chilling account of events, Joran said that he and Natalee kissed on the beach but she fought off his further sexual advances and kneed him in the crotch. He angrily kicked her in the head, Joran continued, and then picked up a cinderblock and “yeah, I smash her head in with it completely.” Then he dragged her to the ocean and let her go into the water, he said.

The statute of limitations to bring murder charges in Aruba is 12 years, but a spokeswoman for prosecutors on the island told AL.com that their office would like to see the U.S. Justice Department’s files on Joran “before deciding on the procedural steps to be taken.”

In Aruba, she said, the Natalee Holloway investigation remains open.

Beth, who said she considers her daughter’s case solved, told the site she wouldn’t count on Joran facing murder charges.

“Hopefully, maybe, they will look into that,” she said. “I have what I need…I’m just sticking with victorious right now.”

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