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September 30, 2025 19 mins

With Sean “Diddy” Combs’ sentencing hearing scheduled for this Friday, prosecutors have upped the time they believe Diddy should spend behind bars. They are now asking he serve 11 years for his 2 prostitution convictions. As a part of their request, they included several impassioned letters from his victims, including from star witness and ex girlfriend Cassie Ventura Fines and her parents. Amy and T.J. go over the prosecution’s filings as we all continue to wait for the judge’s ruling on whether to throw out Diddy’s convictions or give him a new trial.

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Speaker 1 (00:02):
Hey there, folks. It's Monday, September the thirtieth, and Sean
Diddy Combs has asked the judge to only sentence him
to fourteen months in prison, meaning he could be out soon.
The prosecutors want him in jail for much, much longer,
and his ex girlfriend Cassie is absolutely letting her voice

(00:25):
be heard saying she too wants him in prison for
a long time. Welcome to this episode of Amy and TJ. Rose.
We were been waiting on Friday, the sentencing hearing for Diddy,
been waiting on this thing. It's this Friday. He wants
fourteen months. Prosecutors, we thought we're asking for four five,
maybe up to six or seven. Eh.

Speaker 2 (00:46):
Yeah, they made they hinted after they had basically said yes,
four to six years, right around when his guilty verdicts
came down. But then we got word that they were
considering asking for longer, and we got the official word
that they want him behind bars for one hundred and
thirty five months, which amounts to eleven years and three months.

Speaker 1 (01:10):
Do that math now, I think Robes we knew there
was going to be a lot of eyes and intrigue
about what this judge is going to do on Friday.
But that is, dear lady, even if he splits the difference,
you talking about five six years in prison, which is
a much different scenario. Yes, the defensive asked for fourteen months.

(01:31):
Time serve is thirteen plus at this point, is it not. Yes, yes,
so it's over thirteen months. He's going home by Thanksgiving
if the judge goes along with that.

Speaker 2 (01:39):
Because credit for good behavior would be applied in by
all accounts, from what we've been able to ascertain, he
has a perfect conduct score so to speak. He's had
no issues that we've heard of, and certainly I believe
we would have heard if anything had gone down in
behind bars, and most certainly his lawyer said, you are
going to be a prisoner. You are going to be

(02:01):
on your best behavior. It's your best shot come sentencing.

Speaker 1 (02:04):
Is that an official thing? You just said that he
got good conduct.

Speaker 2 (02:08):
I just made that up. Yes, But the point basically like, yes,
what you get graded for could apply to how you
are as a prisoner. I would imagine some sort of
grading system, so to speak. But this has been all
on the heels of waiting for this judge to make
a ruling on the hearing we had last week where
he said very shortly he was going to decide whether

(02:31):
or not to throw out the charges against Diddy or
grant him a new trial. And it's so interesting, and
we don't know how this plays into all of this
sentencing when we don't even have the judge having made
a decision that he said he was going to make
quickly that he hasn't made yet.

Speaker 1 (02:50):
So as we speak here on Tuesday, we are waiting
for a judge to before we even get to sentencing,
he said he is going to rule on whether or
not he's going to throw out the convictions or give
him a new trial. So what we're talking we're standing
here robes and the reason this is now a little
more intriguing. All the legal experts afterwards say, yeah, this

(03:10):
isn't going to happen. Of course he's not going to
throw out you. But now it's taken so long that
people are taking little pauls and going way, is the
judge really considering giving Diddy a new trial? Is he
really considering throwing out the two convictions?

Speaker 2 (03:24):
It seems so Look, people are always trying to read
the tea leaves when it comes to juries or judges,
And it's always been a general rule of thought that
if a jury takes a long time to come up
with a verdict, it's mostly in the defendant's favor, because
if they wanted to convict, they would probably have done
that quickly. So a lot of folks thinking, well, the

(03:45):
judge is certainly taking a long time. What if he
is actually considering the defense's ask, Wow, that's.

Speaker 1 (03:53):
Okay now, So we're standing by for that. And as
we stand by for this again, Robes, we listen to
you every day, say listen followed every day of this trial,
and it was a shocker after shocker after shocker. Every
time you think you have been shocked enough, they come
up with something else you didn't think. And this is
another twist. I think this is another twist. Ropes. I
didn't necessarily consider co being the one of the judge

(04:14):
considering throwing out the convictions. The other part I didn't consider, Robes,
is this eleven years and the prosecution essentially give a
sentencing memo to the judge, and some of their language
in there are trying to I mean, they are doubling
down and just reiterating some of the same points they
made about him during trial. This is a bad dude,
that's right.

Speaker 2 (04:34):
They said that he has been unre unrepentant. I can't
say that which factors in or they wanted to be
factored in by the judge in terms of sentencing, and
they said this. The defendant will not be punished for
any crimes of which he was acquitted, of course, but
here's the butt. Punishment for his crimes of conviction must

(04:54):
take into account the manner in which he committed them,
meaning there was f physical threats and physical violence.

Speaker 1 (05:02):
I think that isn't that? The key to how much
time he spends in prison is where the judge comes
down on that question. If he only sentences him for
what the charges are and the conviction transportation to engage
in prostitution, the defense argues he didn't profit from it
and he didn't have sex with anybody as far as

(05:23):
the payment. So you're really going to send him to
prison for what is essentially being a john and he
didn't even have sex. They are making an argument about that.
The prosecution isn't this, can he consider aggravating factors?

Speaker 2 (05:38):
The judge, well, he has when it has come down
to his bill.

Speaker 1 (05:42):
Okay, then if that being the case. I don't know
if the legal standard changes, but the argument is, yes,
it was these two counts, but look at the manner
in which he executed them.

Speaker 2 (05:53):
And to point out, each one of those convictions carries
a sentence up to ten years each, so he could
be technically sentenced to twenty years if the judge wanted
to do so.

Speaker 1 (06:05):
Yeah, I don't know where. I mean, obviously we don't
know where the judge is going to come down on this.
Reading tea leaves and reading what this judge has done,
he has not at all been on the side of
the defense when it comes to getting Diddy out of
prison or shortening any times at all. I mean, he
could have let him out while sentencing was being determined.
He didn't even let him out for a couple of.

Speaker 2 (06:24):
Months, that's right. And the prosecutors went on to say
this in their request for those eleven years and three months.
They said the sentence imposed on the defendant should reflect
the substantial psychological, emotional, and physical damage he has inflicted.

Speaker 1 (06:41):
It's not just the crime, they are saying, it's not
just the things he's been convicted of. Based on what
the judge has done previously. I would say he's not
going to buy that. However, I'm not a lawyer, and
I don't know if there is a different standard now
that he has been.

Speaker 2 (06:57):
Convicted, and in terms of that substantial psychological, emotional and
physical damage that the prosecutors are referencing. Cassie, his ex
girlfriend and certainly the star witness of the trial, actually
took time and wrote an impassioned letter to the judge
to the court to try and convince the judge to

(07:20):
keep Ditty behind bars for as long as possible.

Speaker 1 (07:25):
I mean, you know, she had to sit in that
courtroom eight and a half months pregnant, was she not?

Speaker 2 (07:30):
Yes, she says she was nine months pregnant.

Speaker 1 (07:34):
Sitting in front of that guy at nine months pregnant
that you say terrorized you to this point. Hell, we
saw the terror on video. We saw a part of it.
And I don't know what was going through his head
at the mind at the time. But they're reading this
letter now. It's one thing to come and testify and
be compelled to testify. She didn't have to write this letter.

(07:56):
This is a more personal This the thing that this
would piss him all more than maybe anything she said
in court, just telling of story in core is one thing.
Now she is actively arguing keep him in prison for
as long as possible.

Speaker 2 (08:11):
And so we do have parts of the letter we're
going to read to you because they are compelling. Cassie
wrote this to the court for four days in May,
while nine months pregnant with my son. I testified in
front of a packed courtroom about the most traumatic and
horrifying chapter in my life. I testified that from age nineteen,
Sean Combs used violence, threats, substances, and control over my

(08:34):
career to trap me in over a decade of abuse.
He groomed me into performing repeated sex acts with hired
male sex workers during multi day freak offs, which occurred
nearly weekly. While defense attorneys at trial suggested that my
time with Combs was akin to a great modern love story,
nothing could be further from the truth. Nothing about this

(08:55):
story is great, modern, or loving. This was a horrific
death of my life, stained by abuse, violence, forced sex,
and degradation.

Speaker 1 (09:05):
Do you remember that part of the Do you remember that?
I think it was Agnaphillo that was making an argument
in court about this being some type of a love
story that was complicated. That's different, that's not traditional, and
that given some of the stuff we heard and her
being in the middle of it, that had to feel awful.

Speaker 2 (09:25):
That felt icky to me listening to him say that,
because he didn't just slightly amend what she was saying.
He took it in a completely opposite direction in how
he categorized it, and it for me felt icky. That's
just the best word I can think of.

Speaker 1 (09:42):
But all the stories we heard, baby Oi freak off,
a mess in a hotel room, all this.

Speaker 2 (09:47):
Thing, the video we saw, that's not a great modern
love story.

Speaker 1 (09:50):
That's abuse.

Speaker 2 (09:52):
That's physical abuse.

Speaker 1 (09:53):
She addressed that specifically. I bet that was important for
her to get that point in there.

Speaker 2 (09:57):
She went on to say, as private and quiet, oh
she's says she is. She's trying to be as proh.
She tries to keep as private and quiet as I
possibly can, because I am so scared that if he
walks free, his first actions will be swift retribution towards
me and others who spoke up about his abuse at trial.

Speaker 1 (10:19):
I mean it, Look, I don't know the man, and
I'm sure she and a lot of people we've talked
to still fear him who are in his circle. But
how much of an idiot would you have to be
if you get a second chance in life to go
back that route? Now a lot of people say, yeah,
he's crazy. He absolutely would seek revenge, But how could

(10:40):
he not be laying as low as possible if he
was blessed to get a second chance.

Speaker 2 (10:44):
But didn't the judge point out at trial that even
when he knew that he was being investigated, he's still
physically abused his then girlfriend and forced her to do
things she didn't want to do with thee of violence,
even while he knew he was being investigated. Yep. So

(11:05):
that flies in the face of that, and that certainly
is something the judge is not going to forget because
he's the one who pointed it out at trial. Cassie
goes on to say, this disgusts me. He is not
being truthful, the idea that he could reform, that he
could change. I know that who he was to me,
the manipulator, the aggressor, the abuser, the trafficker, is who

(11:26):
he is as a human. He has no interest in
changing or becoming better. He will always be the same cruel,
power hungry, manipulative man that he is.

Speaker 1 (11:38):
That's strong she is of somebody who knows him and
knows him really really well says it is impossible for
him to change. That was a strong words. Is it
a judge, you're going to take that into account. I mean,
he reads all these statements, I presume, But I mean
she is saying he's incapable, disgusted at the idea of
anybody talking about him being a different man, a different person.

(12:01):
That's an indictment on him as a breathing human being
walking planet Earth that is different.

Speaker 2 (12:08):
With him for ten years. I think it's also interesting,
you know a lot of this. The defense argued that
it was drug fueled, that he was under the influence,
that he was out of his mind while in prison. Obviously,
he has had to be clean and sober or at
least you know, I know that there are constant there's
constant talk about drugs being in prison. But let's presume

(12:31):
or assume he has been sober the entire time while
behind bars. So could we have a different Sean Diddy
Coombs because he's sober and because he's not in these
drug fueled states of aggression or anger or violence. Who knows,
but I thought this ls. So this was a three
page letter that Cassie wrote to the judge. But I

(12:52):
thought this next paragraph was really compelling and really powerful.
She writes. While the jury did not seem to understand
or believe that I engaged in freak offs because of
the force and coercion defendant used against me, I know
that is the truth, and his sentence should reflect the
reality of the evidence and my lived experience as a victim.

Speaker 1 (13:17):
Legally, I don't know if the judge can take in
to account something a statement that emotional and for an
experience that personal to her. I don't know if he can.
It's hard to understand how you could ignore that if
you're legally allowed to take it into account. But stay

(13:37):
with us, because folks, I read the entire letter. We
read all three pages of what she had to say,
and it was painful. It was heart wrenching. But we're
going to read for you when we come back. Something
her parents said that maybe hit harder than anything else.

Speaker 2 (14:06):
Welcome back to this edition of Amy and TJ. We
are talking about the prosecution in the Ditty case asking
for a much larger sentence than they had initially suggested
they were going to ask for. They have asked the
judge to sentence Sean Dittycomb's to eleven years and three
months behind bars. That's a far cry from the fourteen

(14:26):
months that the defense is asking for. And among the
files that they presented to the judge, or what they
submitted to the judge, was this three page letter by
Cassie Ventura Fines, of course the star witness during the trial,
but also there were several other testimonials from other victims,
but notably a letter from Cassie's own parents.

Speaker 1 (14:49):
Look, this is I think her mom was the one
during the trial, right, she testified. I think she was
only up there for a fifteen minutes half hour at most,
but they only had a couple of questions for her,
and she gave some really difficult testimony. Bro it was
the twenty thousand don't have them ount right?

Speaker 2 (15:03):
I believe it was twenty thousand dollars.

Speaker 1 (15:05):
When Diddy, essentially the story goes, told her, yeah, you
can have your daughter back for twenty thousand, which is
what Sean Combs was arguing. He had invested in her
as an artist. Family sent the money, mortgaged their home
to essentially buy their daughter's freedom from this guy. He

(15:28):
sent the money right back. They ended up getting the
money back and the deal was off when she told
that story of how we were willing to do that
to get our kid back. And that's what I thought
about the mom and thinking about her parents and that
story they told. But they added this line. They had
an entire letter, but they said it this way. This
letter from Cassie's parents to the judge.

Speaker 2 (15:48):
To sentence lightly in this case that involves such vicious
abuses of our daughter's body, safety, and dignity is to
dismiss her very existence. To sentence lightly would also send
a dangerous message. A sentence that is handed down in
months instead of years sends a message that such repulsive

(16:10):
behavior can happen without meaningful consequence.

Speaker 1 (16:13):
The repulsive behavior. Is he being sentenced for repulsive behavior
or for two counts of being a john who didn't
even have sex with the prostitute that he hired.

Speaker 2 (16:25):
I think the prosecution wants both of those things considered.

Speaker 1 (16:28):
Yeah, and that is going to be the key. But
to hear them say it that way, to see that
we had a victim that was on every single television screen.
We're seeing her being beaten. We heard all these details
about violence and disease, and forced sex and fight. We've
heard all this, and you're telling me at the end

(16:50):
of that you're going to give him fourteen months. From
just a public standpoint, that does a lot of damage
for moving forward and how we deal with treat respect,
listen to trust, believe survivors.

Speaker 2 (17:05):
Yes, and a lot of victims' advocates and victims themselves
of any kind of domestic or sexual abuse have spoken
up and said this is going to prevent more people
who are suffering from coming forward because they will feel
unsupported and not believed and probably think to themselves it's
not worth it. And so this might silence people who

(17:27):
should speak up, who need to speak up, because they
won't feel supported, they won't feel like they have a
path forward legally because they just aren't believed.

Speaker 1 (17:37):
Could be a message to the government as well in prosecutions.
A lot of arguments not just from didyside, over prosecution
going after him as a mob boss when this is
a guy who was into some terrible stuff, maybe behind
the scenes in his personal life, and yes, some criminal
activity that didn't rise to that level. That could send
a message to prosecutors on the road about how to

(18:01):
handle these cases. But this has turned out it's just
Tuesday robes, and this has turned out to be a
little more fascinating of a week in this case than
we thought it. Thought it was gonna be cut and dry.
Get to Friday and we'll see what happens. But now
eleven years versus fourteen months, Cassie speaking out in letters
and still waiting on a decision about if the judge

(18:23):
is going to throw out the conviction. So we're going
to stay on top of all that. As always, we
need to give a reminder on your Apple podcast app
top right corner, click follow, where you see our show
page you can get all our updates coming to you.
And their robes have been so many more than we
expected on this story this week.

Speaker 2 (18:40):
I suppose certainly so. And yes, we are still waiting
to hear from the judge on whether or not he
will toss the convictions, give Ditty a new trial, or
just say let's move on to sentencing, which of course
is Friday. So we will keep our ear to the
ground and let you know anything we hear in the meantime, though,
thank you for listening. I'm Amy Robach alongside TJ. Holmes.

(19:00):
We'll talk to you soon.
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