Podcast Summary

Podcast: Drop Dead Serious With Ashleigh Banfield

Episode: Florida Cheerleader Found Dead & Stuffed Under a Cruise Ship Bed: What Really Happened to Anna Kepner?
Release Date: November 21, 2025
Host: Ashleigh Banfield
Guest: Josh Boswell, Senior Reporter, DailyMail.com

Overview

In this episode, Ashleigh Banfield delivers an in-depth, emotionally-charged exploration of the mysterious death of Anna Kepner, an 18-year-old Florida cheerleader found dead and concealed under her cruise ship bed. The host details the troubling family dynamics, disturbing allegations regarding Anna's stepbrother, and the hurdles faced by investigators operating under international maritime law. Emphasis is placed on the lack of concrete evidence or official statements while underscoring rampant suspicions and the secrecy surrounding the investigation.

Key Discussion Points & Insights

Personal Loss and Setting the Tone

• Ashleigh Banfield opens with a heartfelt tribute to her late dog Atlas (00:05 – 02:35), a mainstay of her podcast, sharing her grief and how it impacts the show’s atmosphere.

“He is in the studio with me all the time, and when we're not in the studio, he was at my side all the time. ... This is a big change for me. But I'm going to forge ahead.” — Ashleigh Banfield (01:30)

Case Background: Who Was Anna Kepner?

• Anna Kepner was a high school senior from Florida, traveling with her blended family on a Carnival cruise – a trip including her biological brother, stepbrother, father, stepmother, and her stepmother’s children. (02:50)
• Anna’s relationship with her 16-year-old stepbrother appears fraught and inappropriate, with multiple sources describing his “obsession” and concerning behaviors toward her.

Disturbing Allegations about Anna’s Stepbrother

• Ex-boyfriend's father claims Anna’s stepbrother was obsessed and crossed boundaries:

“He saw her stepbrother come in the room when she was sleeping and get on top of her.” — Anna’s ex-boyfriend’s father (03:42)

“I tried to tell the parents that this was happening and they didn't want to believe me. He's like infatuated, attracted to her like crazy. He’s always after her.” (03:54)

• Further threats: Anna reportedly feared her stepbrother, who always carried a large knife. (04:04)
• Family turmoil highlighted: Anna’s biological mother, estranged and allegedly not informed of Anna’s death, described being banned from the memorial and considering attending in disguise. (04:40)

“I'm going to put a wig on and wear some really tall shoes because I'm 4 foot 9.” — Anna’s mother (04:40)

Evidence and Timeline of Events

• Surveillance Footage:
  • Anna is last seen returning alone to her cabin the night of November 6, excusing herself from dinner because she felt unwell. (04:42)
  • Stepbrother and brother return to the cabin later, separately. The younger brother leaves again, returns, and does not see Anna; presumes she went out. (05:00)
  • Anna’s body is discovered the next morning by cleaning staff, having been stuffed under her bed and covered in blankets and life jackets. (05:20)

“The younger boy, her brother then leaves again reportedly to take pictures of the ship... He went to bed, off to sleep on his bunk bed, never knowing that Anna's body was stuffed underneath her own bed, just mere feet away from him.” — Ashleigh Banfield (05:00)

Interview with Josh Boswell, DailyMail.com

Discussion Topics (06:27–11:20):

• No official cause of death:

  • The FBI has not declared Anna’s case a homicide. The coroner has not released any findings. (06:45; 10:55)

• Surmise from CCTV:

  • CCTV shows Anna entering her cabin, with no footage of her leaving.

  “There is CCTV footage that it shows Anna going back into that room and never coming out again.” — Josh Boswell (07:23)

• Witness accounts of conflict in the cabin:

  • Anna’s younger brother reportedly told the ex-boyfriend he heard “shouting, screaming, what sounded like furniture being thrown,” and that the stepbrother blocked entry to the room.

  “He tried to get back into the room and the stepbrother blocked his way and told him to leave.” — Josh Boswell (07:50)

• Timeline uncertainties:

  • Anna leaves dinner early (Nov 6), returns to the cabin, by the next morning (Nov 7), her absence is noticed, and her death is pronounced at 11:00 AM—but she likely died during the night. (09:16)

• Toxicology and investigation:

  • No information has been released on toxicology results. FBI is expected to pursue “every method.” (10:55)

Legal Complexity: International Waters & Juvenile Protections

• Jurisdictional difficulties:

  • The FBI has jurisdiction because the ship was in international waters, complicating investigative transparency and speed. (11:33)
  • If the stepbrother is involved, federal law provides extra privacy/protection for juveniles, making details less accessible. (12:10)

• How the stepbrother became a suspect:

  • Not through FBI statements, but via court filings: The stepbrother’s parents, amid a custody dispute, revealed he is considered a person of interest by the FBI.

  “The only reason we know that this kid is a suspect at all in this case is... from custodial filings. ... The parents themselves have said so...” — Ashleigh Banfield (13:20)

Family Dysfunction and Uncertainty

• Custody battle spotlight:
  • The 16-year-old’s parents “are fighting over custody... and they're filing all these competing custodial papers with the court.” The boy is reportedly with another relative, not either parent. (14:10)
  • Banfield's critical commentary:

  “Have you two fucking idiots lost the plot? You really fighting over custody at this point? You might want to join forces because your 16-year old kid could be up on murder if that's where this case is going to.” — Ashleigh Banfield (14:45)

Reflections, Theories, and Continuing Mystery

• Caution on assumptions:
  • Banfield reiterates that no one—including the 16-year-old stepbrother—has been officially charged.
  • She suggests, from experience, that teenagers don’t usually commit “perfect crimes” and implies an eventual resolution is likely—if he’s responsible. (16:00)

“Kids who are 16, they're not very good criminals. ... They do stupid shit like stuffing a body under a bed and thinking, there you go, nothing more to see here.” — Ashleigh Banfield (16:00)

Notable Quotes & Memorable Moments

• Emotional introduction about Atlas:

  “On the day he died, he had a whole bunch of these big ones and an ice cream sundae. The vet made an ice cream sundae for Atlas... It was a very, very hard day. And I'm not gonna lie, it's been a really hard time.” (01:40)

• On cruise ship investigations:

  “Everyone who goes on a cruise should know it ain't the same when you're on the high seas. ... you don't get the same kind of policing you would if something happens here at home.” (11:33)

• On family custody disputes amid tragedy:

  “They're still bitching and moaning about who gets the 9 year old. ... It is a mess, y’all, but hopefully there'll be some resolution soon.” (15:00)

Important Timestamps

• 00:05 – 02:35: Ashleigh’s tribute and emotional note about Atlas
• 02:36 – 04:42: Overview of Anna Kepner’s case, background, family dynamics, and disturbing allegations
• 04:43 – 05:30: Surveillance video details and initial timeline of events
• 06:27 – 11:20: Interview with Josh Boswell, deep dive into evidence, timeline, and investigatory gaps
• 11:33 – 17:00: Legal jurisdictional issues, court filings, family drama, and closing reflections

Tone & Style

Ashleigh Banfield’s approach is a blend of investigative seriousness, irreverent commentary, and personal reflection. She is candid, unsparing in her critique of family dysfunction and investigative secrecy, and brings both sensitivity (especially regarding Anna and Atlas) and sharp skepticism to the unfolding events.

Summary Takeaway

The episode is a sobering, sometimes provocative look at a case still shrouded in mystery and rumor. Banfield emphasizes the murky intersection of family dysfunction, legal complexity, and the challenges of investigating deaths at sea, highlighting how much remains unknown—and how the truth is often not only serious but, as she quips, “drop dead seriously.”