Episodes

  • Sunday 6/8. Bonus: Inside the “Freak Off” Machine — Power, Secrecy, and Survival in Diddy’s World

    Sunday 6/8. Bonus: Inside the “Freak Off” Machine — Power, Secrecy, and Survival in Diddy’s World
    Jun 8 2025
    With the courtroom dark for the weekend, Nate Oliver pulls back the curtain on the infamous “freak off” parties at the heart of the Diddy trial. Through chilling testimony from Cassie, assistants, hotel staff, and male escorts, discover how these nights were meticulously planned, enforced with NDAs and cash, and fueled by drugs, fear, and control. From luxury suites trashed with oil and candle wax to the psychological toll on everyone involved, this episode exposes the machinery of silence, blackmail, and trauma behind the headlines. Did He Do It? delivers the most in-depth look yet at the secret rituals that prosecutors say powered Diddy’s empire.






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    9 mins
  • Saturday 6/7. “Broken, Exhausted, and Desperate to Escape” — Jane’s Shocking Account of Diddy’s ‘Freak Offs’

    Saturday 6/7. “Broken, Exhausted, and Desperate to Escape” — Jane’s Shocking Account of Diddy’s ‘Freak Offs’
    Jun 7 2025
    On Day 25, the trial’s focus shifts to Jane, whose graphic testimony reveals a world of relentless sexual coercion, drug-fueled “freak offs,” and psychological manipulation. Jane recounts how Diddy orchestrated hotel nights, forced her into encounters with male escorts, and threatened her home and safety if she refused. With photos, audio, and a paper trail of cash and text messages, the prosecution builds its most disturbing case yet. Nate Oliver breaks down every harrowing detail and what it means as the trial enters a new phase.

    Unlock an ad-free podcast experience with Caloroga Shark Media! Get all our shows on any player you love, hassle free! For Apple users, hit the banner on your Apple podcasts app. For Spotify or other players, visit caloroga.com/plus. No plug-ins needed!

    Subscribe now for exclusive shows like 'Palace Intrigue,' and get bonus content from Deep Crown (our exclusive Palace Insider!) Or get 'Daily Comedy News,' and '5 Good News Stories’ with no commercials! Plans start at $4.99 per month, or save 20% with a yearly plan at $49.99. Join today and help support the show!

    We now have Merch! FREE SHIPPING! Check out all the products like T-shirts, mugs, bags, jackets and more with logos and slogans from your favorite shows! Did we mention there’s free shipping? Get 10% off with code NewMerch10 Go to Caloroga.com

    Get more info from Caloroga Shark Media and if you have any comments, suggestions, or just want to get in touch our email is info@caloroga.com
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    9 mins
  • Friday 6/6 Day 25. “I Still Wake Up Screaming” — Bongolan’s Balcony Terror, Bruises, and Diddy’s Fury

    Friday 6/6 Day 25. “I Still Wake Up Screaming” — Bongolan’s Balcony Terror, Bruises, and Diddy’s Fury
    Jun 6 2025
    Day 25 erupts as Bryana Bongolan faces fierce cross-examination, standing firm on her story of being dangled over a 17-story balcony by Diddy. She reveals new threats, chilling flashbacks, and the lifelong trauma she and Cassie endured. Forensic experts and Bad Boy’s ex-CFO back up her account with photos, payment records, and a paper trail of hush money and cover-ups. With the judge warning Diddy for trying to sway the jury and the prosecution previewing more victims, Nate Oliver unpacks every explosive moment from a day that left the courtroom—and the country—shaken.

    Unlock an ad-free podcast experience with Caloroga Shark Media! Get all our shows on any player you love, hassle free! For Apple users, hit the banner on your Apple podcasts app. For Spotify or other players, visit caloroga.com/plus. No plug-ins needed!

    Subscribe now for exclusive shows like 'Palace Intrigue,' and get bonus content from Deep Crown (our exclusive Palace Insider!) Or get 'Daily Comedy News,' and '5 Good News Stories’ with no commercials! Plans start at $4.99 per month, or save 20% with a yearly plan at $49.99. Join today and help support the show!

    We now have Merch! FREE SHIPPING! Check out all the products like T-shirts, mugs, bags, jackets and more with logos and slogans from your favorite shows! Did we mention there’s free shipping? Get 10% off with code NewMerch10 Go to Caloroga.com

    Get more info from Caloroga Shark Media and if you have any comments, suggestions, or just want to get in touch our email is info@caloroga.com
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    9 mins
  • Thursday 6/5 Day 24. “I Thought I Was Going to Die” — Balcony Terror, Bribes, and the Walls Closing In

    Thursday 6/5 Day 24. “I Thought I Was Going to Die” — Balcony Terror, Bribes, and the Walls Closing In
    Jun 5 2025
    Day 24 is a gut punch as Cassie’s friend Bryana Bongolan tells the jury how Diddy dangled her over a 17-story balcony and hurled her onto a table in a fit of rage. Forensic experts replay the infamous hotel assault video, while Bad Boy’s ex-CFO exposes the cash, cover-ups, and hush money fueling Diddy’s empire. With security tight and emotions raw, the prosecution unveils a world of threats, NDAs, and payments to silence witnesses. As the defense scrambles and celebrity names swirl, Nate Oliver unpacks every chilling twist from the most harrowing day yet on Did He Do It?

    Unlock an ad-free podcast experience with Caloroga Shark Media! Get all our shows on any player you love, hassle free! For Apple users, hit the banner on your Apple podcasts app. For Spotify or other players, visit caloroga.com/plus. No plug-ins needed!

    Subscribe now for exclusive shows like 'Palace Intrigue,' and get bonus content from Deep Crown (our exclusive Palace Insider!) Or get 'Daily Comedy News,' and '5 Good News Stories’ with no commercials! Plans start at $4.99 per month, or save 20% with a yearly plan at $49.99. Join today and help support the show!

    We now have Merch! FREE SHIPPING! Check out all the products like T-shirts, mugs, bags, jackets and more with logos and slogans from your favorite shows! Did we mention there’s free shipping? Get 10% off with code NewMerch10 Go to Caloroga.com

    Get more info from Caloroga Shark Media and if you have any comments, suggestions, or just want to get in touch our email is info@caloroga.com
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    10 mins
  • Wednesday 6/4 Day 23. Cash, Cover-Ups, and Celebrity Fallout — Diddy’s Empire on the Brink

    Wednesday 6/4 Day 23. Cash, Cover-Ups, and Celebrity Fallout — Diddy’s Empire on the Brink
    Jun 4 2025
    Day 23 delivers explosive courtroom revelations as former hotel security supervisor Eddy Garcia exposes Diddy’s desperate attempts to erase damning surveillance footage. Financial insiders reveal the inner workings of Diddy’s empire, while the prosecution unveils payment records hinting at hush money. The trial’s cultural impact deepens with celebrity mentions and political attention, including President Trump’s comments and 50 Cent’s vow to oppose clemency. As the prosecution nears the end of its case, new witnesses and evidence promise even more drama. Nate Oliver breaks down every twist and turn in this pivotal episode of Did He Do It?







    Unlock an ad-free podcast experience with Caloroga Shark Media! Get all our shows on any player you love, hassle free! For Apple users, hit the banner on your Apple podcasts app. For Spotify or other players, visit caloroga.com/plus. No plug-ins needed!

    Subscribe now for exclusive shows like 'Palace Intrigue,' and get bonus content from Deep Crown (our exclusive Palace Insider!) Or get 'Daily Comedy News,' and '5 Good News Stories’ with no commercials! Plans start at $4.99 per month, or save 20% with a yearly plan at $49.99. Join today and help support the show!

    We now have Merch! FREE SHIPPING! Check out all the products like T-shirts, mugs, bags, jackets and more with logos and slogans from your favorite shows! Did we mention there’s free shipping? Get 10% off with code NewMerch10 Go to Caloroga.com

    Get more info from Caloroga Shark Media and if you have any comments, suggestions, or just want to get in touch our email is info@caloroga.com
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    10 mins
  • Tuesday 6/3 Day 22. “Brainwashed by Fear” — Mia’s Final Stand and Diddy’s Hotel Secrets

    Tuesday 6/3 Day 22. “Brainwashed by Fear” — Mia’s Final Stand and Diddy’s Hotel Secrets
    Jun 3 2025
    Day 22 delivers a courtroom marathon as Mia, Diddy’s ex-assistant, endures a brutal cross-examination and reveals the psychological warfare behind her years of silence. Hotel managers and forensic experts expose the aftermath of Diddy’s wildest nights—aliases, trashed suites, and surveillance footage of violence. With the prosecution hinting at new bombshell witnesses and the defense ready to strike back, Nate Oliver unpacks every emotional twist, celebrity ripple, and looming showdown as the Diddy trial barrels toward its most pivotal week yet on Did He Do It?

    Unlock an ad-free podcast experience with Caloroga Shark Media! Get all our shows on any player you love, hassle free! For Apple users, hit the banner on your Apple podcasts app. For Spotify or other players, visit caloroga.com/plus. No plug-ins needed!

    Subscribe now for exclusive shows like 'Palace Intrigue,' and get bonus content from Deep Crown (our exclusive Palace Insider!) Or get 'Daily Comedy News,' and '5 Good News Stories’ with no commercials! Plans start at $4.99 per month, or save 20% with a yearly plan at $49.99. Join today and help support the show!

    We now have Merch! FREE SHIPPING! Check out all the products like T-shirts, mugs, bags, jackets and more with logos and slogans from your favorite shows! Did we mention there’s free shipping? Get 10% off with code NewMerch10 Go to Caloroga.com

    Get more info from Caloroga Shark Media and if you have any comments, suggestions, or just want to get in touch our email is info@caloroga.com
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    9 mins
  • Monday 6/2 Day 21. Secrets, NDAs, and the Price of Silence — Diddy’s World on Trial

    Monday 6/2 Day 21. Secrets, NDAs, and the Price of Silence — Diddy’s World on Trial
    Jun 2 2025
    As the Diddy trial resumes, Nate Oliver digs into the untold details from last week’s testimony. Hear how former insiders described a world ruled by fear, ironclad NDAs, and threats of financial ruin for anyone who spoke out. From Capricorn Clark’s harrowing stories of violence and intimidation to Mia’s revelations about hush money, psychological survival, and Diddy’s grip on Cassie’s life, this episode unpacks the hidden machinery of control at Bad Boy. With new witnesses and twists expected this week, Did He Do It? brings you the secrets and stakes behind the headlines.

    Unlock an ad-free podcast experience with Caloroga Shark Media! Get all our shows on any player you love, hassle free! For Apple users, hit the banner on your Apple podcasts app. For Spotify or other players, visit caloroga.com/plus. No plug-ins needed!

    Subscribe now for exclusive shows like 'Palace Intrigue,' and get bonus content from Deep Crown (our exclusive Palace Insider!) Or get 'Daily Comedy News,' and '5 Good News Stories’ with no commercials! Plans start at $4.99 per month, or save 20% with a yearly plan at $49.99. Join today and help support the show!

    We now have Merch! FREE SHIPPING! Check out all the products like T-shirts, mugs, bags, jackets and more with logos and slogans from your favorite shows! Did we mention there’s free shipping? Get 10% off with code NewMerch10 Go to Caloroga.com

    Get more info from Caloroga Shark Media and if you have any comments, suggestions, or just want to get in touch our email is info@caloroga.com
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    7 mins
  • Sunday 6/1 Bonus: The Rise and Fall of Sean “Diddy” Combs. A biography.

    Sunday 6/1 Bonus: The Rise and Fall of Sean “Diddy” Combs. A biography.
    Jun 1 2025
    With the courtroom on pause, Nate Oliver takes you on a deep, documentary-style journey through the life of Sean “Diddy” Combs. From Harlem tragedy to hip-hop royalty, from Bad Boy’s chart-topping heyday to billion-dollar business moves, Diddy’s story is one of ambition, reinvention, and controversy. But behind the mogul’s empire, witness testimony now paints a chilling portrait of control, violence, and fear. As the trial’s bombshells threaten to rewrite Diddy’s legacy, this special episode traces every triumph, scandal, and turning point—right up to the moment the world waits for a verdict.


    Unlock an ad-free podcast experience with Caloroga Shark Media! Get all our shows on any player you love, hassle free! For Apple users, hit the banner on your Apple podcasts app. For Spotify or other players, visit caloroga.com/plus. No plug-ins needed!

    Subscribe now for exclusive shows like 'Palace Intrigue,' and get bonus content from Deep Crown (our exclusive Palace Insider!) Or get 'Daily Comedy News,' and '5 Good News Stories’ with no commercials! Plans start at $4.99 per month, or save 20% with a yearly plan at $49.99. Join today and help support the show!

    We now have Merch! FREE SHIPPING! Check out all the products like T-shirts, mugs, bags, jackets and more with logos and slogans from your favorite shows! Did we mention there’s free shipping? Get 10% off with code NewMerch10 Go to Caloroga.com

    Get more info from Caloroga Shark Media and if you have any comments, suggestions, or just want to get in touch our email is info@caloroga.com
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    12 mins
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