Separating Fact From Fiction: The Natalee Holloway Case

The following article includes graphic descriptions of murder.

Natalee Holloway was a normal American girl. She was born on October 21, 1986 and was raised by parents Beth and Dave Holloway until they divorced in 1993. From that point, both Natalee and her brother, Matthew Holloway, were primarily under the care of their mother. Natalee grew up in Mountain Brook, a wealthy Alabama suburb. She kept a pet dog named Macy, who she cared for, as shared by her friend, Mallie Tucker, in a 2010 interview with Glamour. "She loved that dog so much; she would color its hair with highlighters and paint its toenails," Tucker told the publication, adding that Natalee was also a lover of everything to do with "The Wizard of Oz." While growing up together, Natalee and Tucker had jobs at Tucker's mother's healthy food outlet over the weekends, and when it came to having a downtime, she and another friend, Claire Fierman, would ride wakeboards and go tubing at the Smith Lake.

At school, Natalee was a member of various clubs, but she enjoyed dancing the most. "Natalee was such a good jazz dancer," Fierman told Glamour. "She was on the school dance team every year." Natalee was also an academically gifted student, who graduated with honors from the local high school. She intended to study pre-med at the University of Alabama, but an exciting post-graduation trip to Aruba fatally ended her life. 

Despite the murky material surrounding the once-cold case, there are enough facts available to paint a truly chilling picture of what happened.

Natalee Holloway was one of about 130 Mountain Brook High School students to arrive in Aruba — a tiny Dutch island in the Caribbean, located just off the coast of Venezuela — for a school trip on May 26, 2005. The entire squad, accompanied by seven chaperons, had been aboard two airplanes. By all accounts, it was a trip Holloway and her classmates were in anticipation of and had gone as far as customizing t-shirts for.

The four-day getaway was fun-filled. "The Aruba Holiday Inn was nice; the beach was beautiful. Natalee and I went snorkeling together," Claire Fierman recalled in her chat with Glamour. "At night everyone got really dressed up to have dinner at the hotel, and afterward people would go to popular hangouts for young people — one was Carlos'n Charlie's."

Many of the teens took part in the island's party scene, but it wasn't as if the group was left entirely to their own devices. Bob Plummer was one of seven adults who went to Aruba as a chaperone for the students. According to his 2006 Fox News interview, chaperones routinely checked on students to make sure everyone was safe and happy.

On the day of Natalee Holloway's disappearance, nothing seemed out of the ordinary at first. According to Bob Plummer's conversation with Fox News, all students were present during three routine checks, including one headcount conducted at dinner. Asked when he last caught sight of Holloway, Plummer said, "I would have to say that it was probably that night in the [Aruba Holiday Inn] casino."

Per an FBI release, Holloway joined several classmates for a final night out on May 29, 2005. The students reportedly met 17-year-old Joran van der Sloot, a teen Dutchman attending Aruba International School. Later that same evening, Holloway and her classmates met up with van der Sloot and his friends at the bar Carlos'n Charlie's.

"We knew from talking to other kids who'd been on the trip that Joran was a regular at the casino, and that Natalee had left Carlos'n Charlie's in the backseat of a car with him," Claire Fierman shared with Glamour. Van der Sloot's young Surinamese friends were later identified as brothers Satish Kalpoe, 18, and Deepak Kalpoe, 21. A silver Honda the group left in reportedly belonged to Deepak.

On the morning of May 30, 2005, Bob Plummer and other chaperones placed the first group of students on a bus headed to the airport. That went swiftly, until it was time for the second (and final) set. "We're getting ready to get the second group together, of which Natalee was a part, and at that point, some of the students came up and said, 'We've not seen Natalee since last night,'" Plummer recounted in his interview with Fox News.

The chaperones assembled the students and began interrogating them. None of Natalee Holloway's schoolmates knew where she was. In the hope that she was simply behind time, her belongings were packed and gathered up, ready for departure. "That way, we'd already have her stuff together so we'd be ready to go without missing her flight," Plummer explained.

According to Mallie Tucker's account of events as told to Glamour, some of the students reported Holloway's disappearance to local Aruban authorities. "The police just calmly took notes on a clipboard, matter-of-factly," Tucker, who got intel from other friends since she missed the trip, revealed. "We didn't know it at the time, but somebody had called Beth [Natalee's mother], and she talked to the authorities."

A travel agent who made the trip possible delivered the disturbing news to Beth Holloway. "We actually called back to Birmingham and talked to one of the ladies that had arranged the trip, and she called Beth," Bob Plummer told Fox News. Although Vanity Fair mistakenly identified the agent, Jody Bearman, as one of the chaperones, the publication gave a clear account of what transpired afterward. "I knew immediately that my daughter had been kidnapped in Aruba," Beth revealed in the 2006 interview. "Natalee has never been late in her life."

Beth was coming from a short weekend getaway of her own when she received the news that her daughter was nowhere to be found. She made a few calls; one to 911, to let them know that she was driving above speed limit because her daughter had been abducted, another to her then-spouse and Natalee Holloway's stepfather, George "Jug" Twitty, and a third to the FBI.

Six hours later, she was aboard a private jet headed to Aruba in the company of Twitty and two of his friends. A hopeful Beth had reportedly reserved an empty seat for her daughter's safe return.

The search for Natalee Holloway immediately after she was declared missing was extensive, so was media coverage of the case, which resulted in the suing of television host Dr. Phil. According to the Los Angeles Times, a flock of people — including local authorities, residents, and travelers — all combined forces to help find Natalee. The country's government offered civil servants a day off work to help with the pursuit. Police Commissioner Gerold Dompig said Aruba spent $3 million on the case, according to the New York Daily News.

On July 2, 2005, the Associated Press (via The New York Times) reported that the Netherlands had provided specialized military aircrafts with advanced search gear that would boost the hunt. Later that month, at the persuasion of Aruba's then-Prime Minister Nelson Oduber, Aruban authorities began cooperating with the FBI. A $1 million reward was set for anyone who had information on the teen's whereabouts. "We are doing everything we possibly can to find out if Natalee's alive out there," Holloway's stepfather, George "Jug" Twitty, said at the time, per CNN.

Despite its efforts in the Natalee case, Aruba wasn't spared from negative publicity. Not only did the investigation overwhelm the tiny nation's resources, but it also cast a horrible light on tourist safety within the Caribbean island and stifled business, in addition to being denounced by Beth Holloway.

Aruban authorities zeroed in on prime suspects Joran van der Sloot, Satish Kalpoe, and Deepak Kalpoe almost immediately. The three young men were among several suspects arrested in the months following Natalee Holloway's disappearance. On June 17, 2005, 26-year-old DJ Steve Croes was arrested in connection with the Natalee case. Paul van der Sloot, Joran's 53-year-old father, was taken into custody a few days later.

Barely two weeks afterward, Croes admitted that he'd fabricated a tale about seeing Natalee being taken back to the Aruba Holiday Inn by eavesdropping on one of the suspects, Deepak Kalpoe. "I heard this guy talking on the phone at the Internet cafe," he confessed, per CNN. "So my story was like almost exactly as his." Croes was let go after 10 days, per CBS News, and just a day after Paul was freed since there wasn't enough information to back up his detention.

On July 5, 2005, the Kalpoe brothers were reportedly let go, only to be arrested again in August of the same year, according to CNN. By September 2005, all suspects and persons of interest had been set free. Beth Holloway exited the island with an assurance that she'd keep seeking justice. "I will never allow my daughter's voice to be silenced, but I have exhausted all my avenues in Aruba," she told The Associated Press (via NBC News). Nearly a year later, her efforts to start a case in the United States hit a wall.

According to AL.com, Joran van der Sloot initially denied having any idea who Natalee Holloway was when approached by investigators. It was only after continuous interrogation that the teen admitted to partying with her and eventually leaving a bar with her, although his story about what happened that night changed over the years. In a March 2006 Fox News interview, van der Sloot admitted to having taken a stroll with Holloway at the beach on the night of her disappearance, after which he was picked by Satish Kalpoe. Holloway, he said, stayed behind. "That's the one thing ... that I did wrong, you know, to leave ... there without her — without actually saying I was going to leave her there," he said.

Van der Sloot's story would be different in February 2008, when he was allegedly captured on a hidden camera confessing to his role in Holloway's death, per Radar. He supposedly told a friend that he dumped her body in the ocean off Aruba after she'd collapsed. Aruban prosecutors attempted to charge van der Sloot based on the tape, but a judge refused the request. Van der Sloot publicly retracted his confession, saying he was under the influence of drugs at the time, ABC News reported.

In November that year, van der Sloot had another tell-all sit-down with Fox News, during which he claimed that Holloway was purchased by a man on a boat at the beach for a little under $10,000 — a story he later alleged to have made up following the interview.

One of the most insidious chapters of Natalee Holloway's case came in March 2010. According to the U.S. Attorney's Alabama Office, Joran van der Sloot promised to provide Natalee's family with the location of their daughter's body, but in exchange for his involvement, he wanted $250,000 from her mother. Van der Sloot reportedly received an initial $15,000 directly into a bank account he owned in the Netherlands. An additional $10,000 advance was paid to a New York law practitioner representing Beth, John Q. Kelly, who handed it to him face to face in Aruba. Van der Sloot retained the money, even after confessing via email that his promised leads were fake.

"I wanted to get back at Natalee's family — her parents have been making my life tough for five years," he told the Dutch daily morning newspaper De Telegraaf months later (via NBC News). "... When they offered to pay for the girl's location, I thought: 'Why not?'"

On June 3, 2010, a federal grand jury formally charged van der Sloot for wire fraud and extortion. Once again, the FBI and Aruban police partnered to bring van der Sloot to book. However, the Dutch national wouldn't immediately get the chance to answer for his actions.

A 21-year-old Peruvian woman named Stephany Tatiana Flores Ramírez was reportedly battered and stabbed to death in a Lima hotel on May 30, 2010, five years after Natalee Holloway's disappearance. Like Holloway, Ramírez was also last seen alive in the company of Joran van der Sloot. Ramírez didn't remain missing for long. Her body was soon discovered in van der Sloot's hotel room.

Unlike Holloway's case, evidence in the Ramírez murder overwhelmingly pointed in the direction of van der Sloot. According to CNN, there was video footage of Ramírez and van der Sloot entering his hotel room together at around 5:30 am on the said morning, and of the Dutchman calmly leaving the room by himself after over three hours.

Van der Sloot soon fled to Chile but was captured just days later, per ABC News. CNN reported that money Ramírez had won from gambling before her unfortunate death amounting to around $1,755 was also missing. Even more incriminating was that van der Sloot was in possession of blood-soiled clothes. Chilean officials then extradited van der Sloot to Peru to answer for Ramírez's murder. Van der Sloot eventually pleaded guilty to murder and robbery charges on January 11, 2012, and he received a 28-year prison sentence two days later.

The death of Stephany Tatiana Flores Ramírez may have had a tie with the Natalee Holloway case, per CNN. According to the outlet, Joran van der Sloot murdered and robbed Ramírez, but a source close to the Peruvian investigation said that authorities believed the victim was killed, in part, because she stumbled on vital evidence in the Holloway case. During several hours of police questioning, van der Sloot allegedly admitted to killing Ramírez after an argument.

An anonymous source claimed the Dutchman left the victim alone in his room while he went out to purchase bread and coffee at a neighboring gas station. The statement was corroborated by video evidence of van der Sloot leaving the hotel and returning with those items. When van der Sloot returned, he reportedly found Ramírez on his laptop. She allegedly found an email connecting van der Sloot to Holloway's disappearance.

CNN reported that, during the murder investigation, van der Sloot offered to finally reveal the location of Holloway's body, presumably in exchange for extradition to Aruba, but Peruvian authorities were reportedly not interested in anything that did not directly involve Ramírez's murder.

On January 12, 2012, just one day after Joran van der Sloot acknowledged guilt in the murder case of Stephany Tatiana Flores Ramírez, an Alabama court declared Natalee Holloway legally dead. The proclamation was made in accordance with the wishes of Natalee's biological father, Dave Holloway, who required a death certificate in order to halt health insurance payments made in Natalee's name and move her college fund to her little brother.

"I prepared myself for this day six and a half [or] seven years ago," Dave told the Associated Press. "... It's emotional, and it'll probably start sinking in in the next few days, and it's something you never get over." Dave further weighed in on the Ramírez case, saying he was hoping her family would find justice and that any slashing of time off van der Sloot's sentence ought to have been the least possible he could get.

Beth Holloway, on the other hand, reportedly didn't approve of the move to declare Natalee dead. "Natalee's father wanted to see this through, and of course it makes me very sad," she said, per CNN.

12 years after Natalee Holloway's disappearance, her family hadn't abandoned hope yet. The Holloway family took to private investigation, which led to the discovery of human remains thought to be Natalee's. The surprising disclosure was made on a 2017 Oxygen series dubbed "The Disappearance of Natalee Holloway." Natalee's father, Dave Holloway, anticipated good news, but he was careful not to be too optimistic. "I was shocked out of my chair when the guy said there were human remains," Dave said in a conversation with ABC News' "Nightline." "I'm hopeful, but then again I have to have the reservations."

Dave couldn't have been more correct in his hunch. Unfortunately, his family suffered yet another blow when the investigation closed with a disappointment: the remains weren't Natalee's. "Out of the four individual bone samples only one was found to be human," the forensic scientist in charge, Dr. Jason Kolowski, told Oxygen. "The mitochondrial DNA bone sample was not a match to [mother] Beth Holloway, and so it was ruled out as being Natalee Holloway." Kolowski also revealed that the identity and sex of the said individual hadn't been established at the time, but they were caucasian with European roots.

Beth Holloway took Oxygen to court in a $35 million lawsuit for compensation and punitive damages in 2018, with claims that the series was not a genuine investigation, per HuffPost.

Over 18 years after Natalee Holloway disappeared without a trace, Joran van der Sloot confessed to killing the teen and extorting her family after being extradited to the United States. He's expected to serve his 20-year sentence for extortion and wire fraud concurrently with his murder sentence in Peru.

According to October 2023 court records, he and Natalee were together on the beach on the day she met her death. Van der Sloot tried to make a sexual move toward her, which was unreciprocated. "She ends up kneeing me on the crotch," the 36-year-old recounted, adding that he struck Natalee's face "extremely hard" with his foot, and she was knocked unconscious. There was an enormous cinder block nearby, one which he used to commit the final heinous crime. "I smash her head in with it completely," he told the court. Van der Sloot testified that he dumped Natalee's body in the ocean, after which he went home on his own. As of this writing, Natalee's case may have run out of time under Aruba's statute of limitations for murder.

Natalee's mother, Beth Holloway, has found the peace of mind she's been seeking all along. "He [van der Sloot] held all the power over me, and I was desperate and just begging him to give me Natalee," she expressed in a conversation with WVTM 13 News, adding, "And then now ... I feel like I have the power and the victory over him, because all he's gonna hear is that jail cell door slam to remind him he's a double murderer."