What happened to 18-year-old Natalee Holloway after she vanished on a 2005 graduation trip to Aruba—and why did the case remain unresolved for nearly two decades? Did investigators miss critical opportunities in the first hours, and can the public trust anything Joran van der Sloot has ever said after years of shifting stories and alleged lies?

In this episode of Debate The News: True Crime, hosts Adrienne Barker and Joseph Lobosco revisit the full timeline of the Natalee Holloway disappearance, from her last known moments after a night out at Carlos and Charlie’s in Oranjestad to the U.S. extortion and wire fraud case, van der Sloot’s Peru imprisonment for the murder of Stephanie Flores Ramírez, and the bombshell 2023 guilty plea and confession that prosecutors say finally explained what happened. The live discussion also debates alleged investigative missteps, corruption claims, the credibility of van der Sloot’s confession, and what a school-sponsored senior trip should have done differently to keep students safe.

Tune in to hear:

May 30, 2005 – Natalee Holloway vanishes in Aruba: Natalee travels from Mountain Brook, Alabama to Aruba with classmates to celebrate graduation. On the final night, she is last seen leaving Carlos and Charlie’s around 1:30 AM with three local young men, including 17-year-old Joran van der Sloot, and then fails to board her flight home as search efforts by land and sea turn up no trace.

June–September 2005 – Arrests, shifting stories, and no charges: Attention centers on van der Sloot and brothers Deepak and Satish Kalpoe, among the last known people with Natalee. The three are arrested on suspicion of kidnapping and murder, but with no physical evidence and inconsistent accounts, they are released without charges.

2006–2007 – Contradictions mount, the case stalls: The hosts walk through how van der Sloot’s story changes repeatedly—claims about dropping Natalee at a hotel contradicted by surveillance, plus later interviews that keep raising questions—while prosecutors still lack the evidence needed to move forward.

November 2007 – Re-arrests and another release: Authorities arrest van der Sloot and the Kalpoe brothers again, but all are released within weeks for lack of evidence, leaving Natalee’s family and the public furious as the investigation loses momentum.

Early 2008 – Hidden camera video and renewed attention: Dutch reporter Peter R. de Vries airs hidden-camera footage that appears to show van der Sloot implicating himself. The case is revisited, but officials cannot corroborate the statements on tape and no charges follow.

March 2010 – FBI sting and extortion scheme: Nearly five years after Natalee disappears, van der Sloot allegedly demands $250,000 to reveal what happened and where her remains are. Beth Holloway alerts the FBI, a sting is arranged, and he receives $25,000 through a mix of cash and wire transfers—then later admits the story he sold the family was “worthless,” leading to federal wire fraud and extortion charges in the U.S.

May 30, 2010 – Stephanie Flores Ramírez is killed in Peru: Exactly five years after Natalee vanished, 21-year-old Stephanie Flores Ramírez is found dead in a Lima hotel room registered to van der Sloot. He flees, is captured days later, and the case becomes a second tragedy tied to the same suspect.

2012 – Natalee is declared legally dead: An Alabama judge declares Natalee Holloway legally deceased as her