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All the Leads That Proved to Be Letdowns in the Natalee Holloway Case

Natalee Holloway vanished nearly 16 years ago and, despite her parents' tireless efforts, a void remains in lieu of answers.

von Natalie Finn Feb 28, 2021 08:00Tags
Weitere: Dave Holloway on Daughter Natalee Holloway's Crime Series

When shards of bone were discovered in Aruba a few years ago, Dave Holloway hoped against hope that DNA testing would prove the remains were of his daughter, Natalee Holloway, who went missing in 2005 while on a high school graduation trip to the Caribbean island. It would be sad, and it would be disturbing, but at least it would be an answer in a case that remains largely composed of questions.

It took a year and a half of working under the radar with the help of an informant to locate the spot where the remains were found, behind a house that had been previously mentioned over the course of the sporadically eventful investigation.

"We've had a number of disappointments and I've put up a wall trying to find something that's not gonna disappoint me," he said on Today in August 2017. "And when we determined that these remains were human, I was shocked, and I know that there's a possibility this could be someone else, and I'm just trying to wait and see."

But that October it was revealed that the mitochondrial DNA wasn't a match to a sample provided by Natalee's mother, Beth Holloway. The bones didn't belong to Natalee.

Another dead end.

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"Out of the four individual bone samples only one was found to be human," forensic scientist Jason Kolowski, who tested the samples, explained to Oxygen, which chronicled Dave's journey with private investigator T.J. Ward as they followed what felt at the time to be their most promising lead in years.

"We don't know if the person is male or female," Jason added. "We don't know how old that person is. We don't know how long that person has been dead."

For nearly 16 years, the investigation into Natalee's disappearance has carried on in fits and spurts, with light occasionally appearing at the end of the tunnel, only to be snuffed out at the first whiff of closure. In the meantime, books have been written, Lifetime made two movies about the case, news-magazine shows have covered it top to bottom, and every theory in the book has been floated—including that Natalee is still alive, or at least was for years after the events of May 30, 2005, transpired.

Whatever those events were, exactly.

Despite all the media attention and so many law-enforcement hours spent trying to find out what happened, definitive answers have remained out of reach. But numerous times, authorities and Natalee's family seemed to be getting closer. "We always felt like with every lead, with every tip, it was always as if we were about to get her," Beth previously told 20/20. "They just always turned up nothing."

Here, all the twists that turned into letdowns over the course of 16 years...

The Missing

Natalee Holloway, 18, grew up in the well-heeled Birmingham, Ala., suburb of Mountain Brook. The teen was the oldest child of Dave and Beth Holloway, who divorced in 1993. She and her younger brother, Matthew, lived primarily with Beth. Natalee was an honors student and member of the school dance team and American Field Service, helping exchange students adapt to life in the U.S. She had earned a full academic scholarship to the University of Alabama and planned to study pre-medicine. 

She was also a regular churchgoer, according to her uncle Paul Reynolds, who told the AP days after his niece went missing, "Natalee's naive. She hasn't dated a lot. She doesn't party a lot."

After graduating from high school on May 24, 2005, the teen went to Aruba for a celebratory trip with more than 100 other classmates. "We were on the beach. We stayed outside all day. You'd usually take a nap, get dressed, go eat dinner, and then go to one of the bars. Come home whenever you wanted," friend Claire Fierman told NBC's Dateline in 2008.

They were due to return to Alabama on May 30, but Natalee didn't show up for the flight home. Her passport, cell phone and packed bags were still in her room at the Holiday Inn. "Natalee being late is a tip-off," her aunt Marcia Twitty told reporters, noting how reliable her niece was.

When the plane took off without her, classmate Laraine Watson told Dateline, "It felt like I was leaving something behind. It was just a horrifying feeling knowing that she was supposed to be there and she wasn't."

Remembering the phone call that informed her Natalee had missed her flight, Beth told Dateline, "I knew instantly when I received that call that just from Natalee's history and character and just her record, I knew instantly that she'd either been kidnapped or murdered. There was no hesitation. Absolutely none. Absolutely none."

She and Dave, with respective friends and family members, flew to Aruba immediately.

Investigators soon determined that Natalee was last seen by classmates leaving a popular nightspot called Carlos 'N Charlie's with soon-to-be household name Joran van der Sloot, then 17, and two brothers, Deepak Kalpoe, 21, and Satish Kalpoe, 18.

Seven Arrests, No Charges

When Aruban authorities first questioned the Kalpoe brothers and van der Sloot, they said they took Natalee 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.

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.

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."

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.

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. 

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. 

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.

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. He wasn't even arrested for wire fraud.

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 Young Woman 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. Upon his release, he faces extradition to the United States, and could face 40 more years in prison if convicted of extortion and fraud.

Face to Face

Beth Holloway went to Peru to visit Joran in prison in 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."

An Endless Search

Dave returned to Aruba in 2015, this time with private investigator T.J. Ward, after a man named Jurrien De Jong came forward claiming he witnessed Joran chasing Natalee into a building that had been under construction—but didn't report it in 2005 because he himself was involved in criminal activity. Again, authorities said the building in question hadn't been built yet in 2005.

Dave told AL.com in 2015 that he was pretty convinced of the theory that Joran had paid a bartender to drug Natalee, after which he killed her and then paid drug runners to dispose of her body elsewhere. "The answers lie in Peru and Aruba,'' he said. "Those three [van der Sloot and the Kalpoe brothers] know exactly what happened. And nobody's ever gotten anything out of them."

The Strangest Twist Yet

On the 2017 Oxygen series The Disappearance of Natalie Holloway, John Ludwick claimed that Joran paid him $1,500 to help dig up Natalee's remains in 2010. They crushed most of the bones, but doused the skull with gasoline and set it on fire, to destroy any hair follicles, he claimed. Ludwick also said Joran told him that Natalee died of a bad reaction to a drug he had slipped her.  

Going on the tip from Ludwick, Dave and T.J. found remains which turned out not to be Natalee's.

In March 2018, Ludwick, 32, was fatally stabbed by Emily Heistand, who said Ludwick was trying to kidnap her at knife-point from her driveway outside her Florida home. She managed to wrestle the knife from him and wound him in the abdomen. Ludwick fled the scene but died of his injuries at a nearby hospital. Authorities concluded Emily acted in self-defense and she was not charged with a crime.

Days after the attack, Emily went on Dr. Phil and said that she once briefly dated Ludwick and he had been stalking her prior to the attack. She also said that Ludwick told her a few months after she first met him that Joran old him that Natalee had died after he drugged her. According to Emily, Ludwick then told her that he helped Joran  get rid of her remains.

"He told me that Joran did do it and hid the body. John told me that Joran got this Natalee girl all drunk at a bar," Emily told Dr. Phil McGraw, "and Joran took her to the beach, and they were having a good time, and she started seizing and foaming at the mouth. And Joran called his dad and helped them dispose of the body."

As for Ludwick, "I was just kind of creeped out by him after that and wanted to stay away from him," she said, later adding,, "Sometimes I feel like I'm a murderer, but then sometimes I'm like 'I did what I had to do.' I don't know how I made it out, but I'm just glad I did."

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." 

Meanwhile, the family of Natalee has had to do everything in its power not to feel trapped in a different sort of prison.

In January 2012, the day before Joran was sentenced to 28 years in prison, a judge declared Natalee legally dead—a necessary move so Dave could access the money he had put into her college fund in order to pay for her younger brother's tuition. He needed a death certificate. "I guess most people do look at anniversaries, but I still think about it every day,'' Dave, who in addition to his and Beth's son Matthew has two other daughters from his second marriage, told Al.com in 2015 as the 10th anniversary of Natalee's disappearance approached. "That's something you'll never get out of your mind."

"The emotional trauma has a way of healing, and a person doesn't realize it until time goes on," he said. "When something comes up significant, you fall back down into that emotional state of trauma. I try to avoid those things as much as I can."

"I look back on it and I wonder how I even made it through," he added. "You're always thinking we're going to get an answer quickly and it never comes. I never dreamed it would be 10 years, and we would not have a solid answer."

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As for Beth, she told Today in 2016, "I have my answer as to what happened to Natalee, and he's sitting in prison in Peru... Justice is being served for Stephany Flores, thank God. And he is in prison in Peru. But justice has not been served for Natalee."

Beth has credited her faith for helping her accept her loss, and she eventually returned to work as a speech therapist at schools in Cullman County. She also traveled the country speaking publicly about Natalee, grief, her family's journey and how to look out for one's personal safety.

"It's a message of hope, and my definition of hope is that inexplicable empowerment that enables us to move successfully from challenge to resolution with courage," she told B-Metro magazine in 2015. "It's more than just wishful thinking. It is real that there is light at the end of the tunnel. No matter what you're trying to find your way through—It could be loss of a loved one, it could be terminal illness, it could be a financial loss. It's a powerful inspirational message that I share that teaches perseverance and hope and that you can endure."

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Going back to Aruba in 2019 was painful, but also cathartic. She has long since accepted that missing Natalee is a part of her daily life. "Every time I looked out at the ocean [on other trips over the years], I couldn't handle it. It just disturbed me greatly," Beth told 20/20. "Because it made me feel as if I was never going to get an answer as to what happened to Natalee. But I feel like I have accomplished a huge feat… I can come back now to Aruba. I can get in the water... It feels great."

She added, "You're never going to get over the...loss of losing your loved one. But life does move on. Natalee would want us to enjoy what life we have left."

(E!, Oxygen and NBC are all members of the NBCUniversal family.)

(Originally published May 30, 2019, at 3 a.m. PT; updated Nov. 23, 2019, at 12:30 p.m. PT)