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Drop Dead Serious With Ashleigh Banfield

Top 10 Moments That Could Lock Diddy Up for Life | United States vs. Sean Combs

Drop Dead Serious With Ashleigh Banfield

Drop Dead Serious With Ashleigh Banfield

True Crime

4.61.1K Ratings

🗓️ 27 May 2025

⏱️ 24 minutes

🧾️ Download transcript

Summary

The federal trial of Sean “Diddy” Combs is underway and prosecutors say it could put him behind bars for life. In this episode of Drop Dead Serious, Ashleigh Banfield counts down the 10 most damning, jaw-dropping moments from the courtroom so far. 

He was the king of Bad Boy Records: a billionaire mogul, a Grammy winner, and the face of luxury in hip-hop. Sean “Diddy” Combs is facing a slew of federal charges in New York, accused of running a criminal enterprise for over two decades. Combs has pleaded not guilty to all charges and maintains his innocence.

Transcript

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0:00.0

Hey everybody, I'm Ashley Banfield and this is Drop Dead Serious.

0:08.3

And if you've been watching the Diddy trial and wondering what on earth is this trial about?

0:13.7

Is it about racketeering or is it about abuse?

0:16.2

I've got a lot of answers for you.

0:18.5

But this particular episode, this one's different because today I'm actually

0:22.4

counting down the 10 most damning and incriminating jaw-dropping moments from the trial so far.

0:29.7

And they're incriminating because the feds are trying to prove racketeering. And they are actually

0:35.7

putting the chain together. So we're going to help you get through

0:38.1

that. And the 10 most damning aspects of this case for Diddy. Prosecution says if they're right,

0:44.6

if they can prove to a jury what they say Diddy is guilty of doing day after day for years,

0:51.8

Diddy could spend the rest of his life behind bars. But if he walks free, these are the

0:56.6

moments that will never, ever leave him. They will never let him enjoy a moment of real peace.

1:03.5

They will never allow him to return to the life that he once had. These are the moments that

1:09.0

will finish off a career that catapulted him to the top of the

1:13.0

A-list, to the top of one percenters, and to the top of ultra-stardom and ultra-wealth. These are the

1:21.7

moments that will torpedo that legacy forever, whether he is found guilty or whether he walks. So buckle up and let's get

1:30.0

right into it. Number 10, let's start with someone on the outside, a man named Israel Flores.

1:37.2

He is currently an officer with the LAPD, but back in 2016, he was a hotel security guard

1:43.9

at the Intercontinental in Los Angeles.

1:46.4

The same hotel where Diddy's longtime girlfriend, Cassie Ventura, was assaulted that year

1:52.5

on camera by Sean Combs. It's the video that is seared into our memories in this trial.

1:59.7

And way more importantly, it is seared into the memories in this trial. And way more importantly, it is seared into the

...

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