June 2, 2025
Monday 6/2 Day 21. Secrets, NDAs, and the Price of Silence — Diddy’s World on Trial
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
Join the Celebrity Trials community on social media! We're building a passionate group of true crime enthusiasts who love diving deep into the most shocking cases in America.
Follow us on Facebook and Instagram by searching "Celebrity Trials Podcast" on either platform. You'll get exclusive behind-the-scenes content, breaking news updates on cases we're covering, and early alerts when new episodes drop. Our social media is where Reid Carter's hottest takes live, including reactions that don't make it into the show.
But more importantly, it's where YOU come in. Share your theories, debate the verdicts, and connect with fellow listeners who are just as obsessed with justice as you are. Did the jury get it right? What questions do you still have? Your comments and insights often shape future episodes.
We cover the trials that matter, but our community makes the conversation unforgettable. Come for Reid's signature cynical commentary, stay for the incredible discussions with thousands of true crime fans who get it.
WEBVTT
1
00:00:00.120 --> 00:00:04.280
Warning. This episode contains references to sexual situations that may
2
00:00:04.320 --> 00:00:07.519
be disturbing to some listeners. Please proceed with caution.
3
00:00:10.960 --> 00:00:19.480
Callaroga Shark Media. Welcome back to Did He Do It?
4
00:00:20.199 --> 00:00:23.839
The Daily podcast bringing you every raw, unfiltered detail from
5
00:00:24.280 --> 00:00:31.000
the Sean Dittycomb's sex trafficking and racketeering trial. I'm Nate
6
00:00:31.039 --> 00:00:34.479
Oliver outside the Manhattan Federal Courthouse on Monday, June second.
7
00:00:34.920 --> 00:00:36.920
As we kick off another pivotal week in a case
8
00:00:36.920 --> 00:00:40.679
that's already up ended the music world. With the courtroom
9
00:00:40.719 --> 00:00:44.359
set to resume, let's go beyond the headlines and revisit
10
00:00:44.439 --> 00:00:47.640
some of last week's most revealing moments, focusing on the
11
00:00:47.679 --> 00:00:52.359
details and perspectives we haven't yet explored. Last week's testimony
12
00:00:52.399 --> 00:00:55.479
brought us deep into the inner workings of Diddy's bad
13
00:00:55.520 --> 00:01:01.280
boy empire. Former assistants, insiders, and friends described a world
14
00:01:01.320 --> 00:01:06.439
where fear, loyalty, and violence were tightly intertwined. Capricorn Clark,
15
00:01:06.439 --> 00:01:08.920
who started as Ditty's personal assistant in two thousand and
16
00:01:09.000 --> 00:01:12.159
four and rose to global brand director, told jurors that
17
00:01:12.200 --> 00:01:14.200
her very first day on the job came with a
18
00:01:14.239 --> 00:01:18.040
threat if her past work for rival rappers ever interfered
19
00:01:18.079 --> 00:01:22.120
with her loyalty, Ditty said he would kill her. Clark
20
00:01:22.200 --> 00:01:24.959
described being present for some of the most violent moments
21
00:01:25.000 --> 00:01:29.400
in Ditty's relationship with Cassie Ventura, including a twenty eleven
22
00:01:29.439 --> 00:01:32.719
incident where she watched in shock as Ditty assaulted Cassie
23
00:01:32.760 --> 00:01:36.000
after learning she was dating Kid Cuddy. Clark's heart was
24
00:01:36.040 --> 00:01:38.079
breaking from seeing her get hit like that, she told
25
00:01:38.120 --> 00:01:43.000
a jury, and neither she nor Ditty's bodyguard intervened. Instead,
26
00:01:43.159 --> 00:01:46.920
Clark called Cassie's mother, pleading please help her. I can't
27
00:01:46.959 --> 00:01:50.680
call the police, but you can. Weeks later, Clark reported
28
00:01:50.680 --> 00:01:53.400
the abuse to the president of Bad Boy Records, but
29
00:01:53.480 --> 00:01:58.560
nothing changed. Clark also described being kidnapped at gunpoint by
30
00:01:58.560 --> 00:02:01.519
Ditty and forced to ride with him as he raged
31
00:02:01.560 --> 00:02:04.640
about wanting to kill kid Cuddy. She said she stayed
32
00:02:04.680 --> 00:02:07.599
in Ditty's SUV while he broke into Cutty's home and
33
00:02:07.719 --> 00:02:10.000
was fired weeks later for what she contends was a
34
00:02:10.000 --> 00:02:13.960
trumped up reason. We also heard from Mia, the second
35
00:02:14.000 --> 00:02:18.199
of three women expected to testify that Ditty sexually assaulted them.
36
00:02:18.800 --> 00:02:22.680
MIA's testimony revealed a world of psychological and physical torment.
37
00:02:23.639 --> 00:02:26.800
She described being forced to work days without sleep, being
38
00:02:26.840 --> 00:02:29.319
doused with ice, thrown into a pool, and having a
39
00:02:29.319 --> 00:02:31.520
bowl of spaghetti flung at her in front of others.
40
00:02:32.639 --> 00:02:35.400
Mia said Diddy raped her during her tenure as his assistant,
41
00:02:35.960 --> 00:02:39.280
and that she frequently witnessed him physically assaulting Cassie at
42
00:02:39.319 --> 00:02:43.680
his homes, hotels, and even at events. Mia explained that
43
00:02:43.719 --> 00:02:47.599
the fear of retaliation kept her and others silent for years.
44
00:02:48.240 --> 00:02:51.960
She described how Ditty's company controlled every aspect of Cassie's life,
45
00:02:52.439 --> 00:02:55.599
from her credit cards to her vehicles and residences, and
46
00:02:55.680 --> 00:02:58.800
how he would confiscate Cassie's belongings whenever he was upset
47
00:02:58.960 --> 00:03:02.680
or couldn't reach her. One of the week's most emotional
48
00:03:02.719 --> 00:03:06.439
revelations came from MIA's recounting of her own severance from
49
00:03:06.479 --> 00:03:10.400
Ditty's world. She testified that after hiring an employment lawyer,
50
00:03:10.879 --> 00:03:14.039
she received a four hundred thousand dollars settlement from Ditty
51
00:03:14.080 --> 00:03:17.080
for wrongful termination, but that she did not mention the
52
00:03:17.080 --> 00:03:20.520
alleged sexual assaults at the time. The defense tried to
53
00:03:20.599 --> 00:03:23.960
use this to suggest her claims were financially motivated, but
54
00:03:24.039 --> 00:03:26.719
Mia insisted the payment was about losing her job, not
55
00:03:26.840 --> 00:03:30.599
hush money. She also described how, years after she stopped
56
00:03:30.639 --> 00:03:34.360
working for Ditty, his bodyguard and Ditty himself reached out
57
00:03:34.400 --> 00:03:38.280
to her after Cassie's civil lawsuit. These were attempts she
58
00:03:38.439 --> 00:03:43.479
interpreted as efforts to influence her testimony. Deonta Nash, Cassie's
59
00:03:43.479 --> 00:03:47.400
longtime stylist and friend, gave further insight into the day
60
00:03:47.439 --> 00:03:51.719
to day reality of Cassie's life under Ditty's control. Nash
61
00:03:51.759 --> 00:03:56.680
described how Ditty dictated Cassie's wardrobe, hair, and even threatened
62
00:03:56.680 --> 00:04:00.479
to have her parents fired if she didn't comply. Nash
63
00:04:00.520 --> 00:04:03.479
recounted a night when Ditty beat Cassie so badly that
64
00:04:03.560 --> 00:04:07.039
she needed stitches, and Nash and another aid tried to
65
00:04:07.080 --> 00:04:10.879
intervene but were thrown off. The violence only stopped when
66
00:04:10.879 --> 00:04:14.280
Ditty saw Cassie's blood, at which point he panicked and
67
00:04:14.400 --> 00:04:16.519
arranged for her to be taken to a plastic surgeon.
68
00:04:17.560 --> 00:04:20.759
Nash described how Cassie would use makeup to cover her injuries,
69
00:04:21.160 --> 00:04:24.000
and how Didty threatened to release explicit videos if she
70
00:04:24.079 --> 00:04:27.000
ever tried to leave or speak out. One detail that
71
00:04:27.040 --> 00:04:29.600
hasn't been widely discussed is how many of Ditty's former
72
00:04:29.639 --> 00:04:34.000
employees and insiders described feeling trapped by strict non disclosure
73
00:04:34.000 --> 00:04:37.199
agreements and the constant threat of financial ruin if they
74
00:04:37.199 --> 00:04:41.199
ever spoke out. Several witnesses testified that they didn't report
75
00:04:41.240 --> 00:04:43.959
the abuse to police because they feared Ditty would harm
76
00:04:44.000 --> 00:04:47.759
them or destroy their careers. The prosecution has argued that
77
00:04:47.800 --> 00:04:50.040
this culture of fear and silence was a key part
78
00:04:50.040 --> 00:04:53.279
of how Didty maintained control over his alleged criminal enterprise.
79
00:04:54.279 --> 00:04:57.040
The week also saw a dramatic moment outside the courtroom.
80
00:04:57.600 --> 00:05:00.839
Cassie Ventura, now thirty eight, delivered her third child less
81
00:05:00.879 --> 00:05:03.680
than two weeks after testifying for four days as the
82
00:05:03.680 --> 00:05:07.240
prosecution star witness. Her absence was felt in the courtroom,
83
00:05:07.319 --> 00:05:10.639
but her testimony continued to reverberate through the accounts of
84
00:05:10.639 --> 00:05:24.519
others more in a moment. Another subplot that's come to
85
00:05:24.560 --> 00:05:28.000
the for is the defense's strategy. Ditty's lawyers have argued
86
00:05:28.040 --> 00:05:33.439
that his relationships, while unconventional and sometimes violent, were consensual,
87
00:05:33.480 --> 00:05:36.199
and that the government is criminalizing his lifestyle and using
88
00:05:36.240 --> 00:05:40.680
the Reicho Statute in an unprecedented way. The defense has
89
00:05:40.720 --> 00:05:43.920
also pointed to MIA's social media posts in which she
90
00:05:44.000 --> 00:05:47.600
called Ditty the good kind of crazy as evidence that
91
00:05:47.680 --> 00:05:51.120
she was not truly afraid of him. Mia countered by
92
00:05:51.120 --> 00:05:54.319
explaining that such posts were a form of psychological survival,
93
00:05:54.839 --> 00:05:59.279
public displays of loyalty to avoid further abuse. The defense
94
00:05:59.279 --> 00:06:03.279
has also seen on procedural issues, including a dramatic motion
95
00:06:03.360 --> 00:06:07.480
for a mistrial after testimony about destroyed fingerprint evidence in
96
00:06:07.519 --> 00:06:11.759
the Kid Cutty Arson case. Judge A run Supermanian denied
97
00:06:11.800 --> 00:06:14.439
the mistrial, but the episode underscored how high the stakes
98
00:06:14.480 --> 00:06:19.560
are for both sides. Looking ahead, the prosecution is expected
99
00:06:19.560 --> 00:06:22.160
to call at least one more alleged victim and more
100
00:06:22.199 --> 00:06:26.120
former employees, while the defense prepares to challenge every detail,
101
00:06:26.279 --> 00:06:30.759
arguing that Ditty's world was wild but not criminal. Prosecutors
102
00:06:30.759 --> 00:06:33.920
have signaled they may finish their case earlier than expected,
103
00:06:34.480 --> 00:06:36.959
but the defense could extend the trial into July as
104
00:06:37.000 --> 00:06:40.600
they present their side, and in a sign of just
105
00:06:40.680 --> 00:06:44.199
how much national attention this case is getting, President Donald
106
00:06:44.199 --> 00:06:46.639
Trump was even asked whether he'd consider a pardon for
107
00:06:46.680 --> 00:06:50.079
Ditty if he's convicted. Trump said he'd certainly look at
108
00:06:50.120 --> 00:06:52.920
the facts, but it was too early to say. This
109
00:06:53.079 --> 00:06:57.959
underscores the trial's cultural and political resonance. This week promises
110
00:06:58.000 --> 00:07:02.560
more twists, more testimony, and more revelations from inside Diddy's world.
111
00:07:03.439 --> 00:07:06.920
I'll be back tomorrow with every new detail, every legal twist,
112
00:07:07.160 --> 00:07:10.800
and every rumor from inside and outside the courthouse. I'm
113
00:07:10.879 --> 00:07:12.639
Nate Oliver, and this is Did He Do It?
114
00:07:19.079 --> 00:07:21.480
This episode of Diddy Did He Do It? Was produced
115
00:07:21.480 --> 00:07:24.879
by Mark Francis and John McDermott for Calaroga Shark Media.
116
00:07:25.519 --> 00:07:27.800
Some AI production assistants may have been used.
1
00:00:00.120 --> 00:00:04.280
2
00:00:04.320 --> 00:00:07.519
3
00:00:10.960 --> 00:00:19.480
4
00:00:20.199 --> 00:00:23.839
5
00:00:24.280 --> 00:00:31.000
6
00:00:31.039 --> 00:00:34.479
7
00:00:34.920 --> 00:00:36.920
8
00:00:36.920 --> 00:00:40.679
9
00:00:40.719 --> 00:00:44.359
10
00:00:44.439 --> 00:00:47.640
11
00:00:47.679 --> 00:00:52.359
12
00:00:52.399 --> 00:00:55.479
13
00:00:55.520 --> 00:01:01.280
14
00:01:01.320 --> 00:01:06.439
15
00:01:06.439 --> 00:01:08.920
16
00:01:09.000 --> 00:01:12.159
17
00:01:12.200 --> 00:01:14.200
18
00:01:14.239 --> 00:01:18.040
19
00:01:18.079 --> 00:01:22.120
20
00:01:22.200 --> 00:01:24.959
21
00:01:25.000 --> 00:01:29.400
22
00:01:29.439 --> 00:01:32.719
23
00:01:32.760 --> 00:01:36.000
24
00:01:36.040 --> 00:01:38.079
25
00:01:38.120 --> 00:01:43.000
26
00:01:43.159 --> 00:01:46.920
27
00:01:46.959 --> 00:01:50.680
28
00:01:50.680 --> 00:01:53.400
29
00:01:53.480 --> 00:01:58.560
30
00:01:58.560 --> 00:02:01.519
31
00:02:01.560 --> 00:02:04.640
32
00:02:04.680 --> 00:02:07.599
33
00:02:07.719 --> 00:02:10.000
34
00:02:10.000 --> 00:02:13.960
35
00:02:14.000 --> 00:02:18.199
36
00:02:18.800 --> 00:02:22.680
37
00:02:23.639 --> 00:02:26.800
38
00:02:26.840 --> 00:02:29.319
39
00:02:29.319 --> 00:02:31.520
40
00:02:32.639 --> 00:02:35.400
41
00:02:35.960 --> 00:02:39.280
42
00:02:39.319 --> 00:02:43.680
43
00:02:43.719 --> 00:02:47.599
44
00:02:48.240 --> 00:02:51.960
45
00:02:52.439 --> 00:02:55.599
46
00:02:55.680 --> 00:02:58.800
47
00:02:58.960 --> 00:03:02.680
48
00:03:02.719 --> 00:03:06.439
49
00:03:06.479 --> 00:03:10.400
50
00:03:10.879 --> 00:03:14.039
51
00:03:14.080 --> 00:03:17.080
52
00:03:17.080 --> 00:03:20.520
53
00:03:20.599 --> 00:03:23.960
54
00:03:24.039 --> 00:03:26.719
55
00:03:26.840 --> 00:03:30.599
56
00:03:30.639 --> 00:03:34.360
57
00:03:34.400 --> 00:03:38.280
58
00:03:38.439 --> 00:03:43.479
59
00:03:43.479 --> 00:03:47.400
60
00:03:47.439 --> 00:03:51.719
61
00:03:51.759 --> 00:03:56.680
62
00:03:56.680 --> 00:04:00.479
63
00:04:00.520 --> 00:04:03.479
64
00:04:03.560 --> 00:04:07.039
65
00:04:07.080 --> 00:04:10.879
66
00:04:10.879 --> 00:04:14.280
67
00:04:14.400 --> 00:04:16.519
68
00:04:17.560 --> 00:04:20.759
69
00:04:21.160 --> 00:04:24.000
70
00:04:24.079 --> 00:04:27.000
71
00:04:27.040 --> 00:04:29.600
72
00:04:29.639 --> 00:04:34.000
73
00:04:34.000 --> 00:04:37.199
74
00:04:37.199 --> 00:04:41.199
75
00:04:41.240 --> 00:04:43.959
76
00:04:44.000 --> 00:04:47.759
77
00:04:47.800 --> 00:04:50.040
78
00:04:50.040 --> 00:04:53.279
79
00:04:54.279 --> 00:04:57.040
80
00:04:57.600 --> 00:05:00.839
81
00:05:00.879 --> 00:05:03.680
82
00:05:03.680 --> 00:05:07.240
83
00:05:07.319 --> 00:05:10.639
84
00:05:10.639 --> 00:05:24.519
85
00:05:24.560 --> 00:05:28.000
86
00:05:28.040 --> 00:05:33.439
87
00:05:33.480 --> 00:05:36.199
88
00:05:36.240 --> 00:05:40.680
89
00:05:40.720 --> 00:05:43.920
90
00:05:44.000 --> 00:05:47.600
91
00:05:47.680 --> 00:05:51.120
92
00:05:51.120 --> 00:05:54.319
93
00:05:54.839 --> 00:05:59.279
94
00:05:59.279 --> 00:06:03.279
95
00:06:03.360 --> 00:06:07.480
96
00:06:07.519 --> 00:06:11.759
97
00:06:11.800 --> 00:06:14.439
98
00:06:14.480 --> 00:06:19.560
99
00:06:19.560 --> 00:06:22.160
100
00:06:22.199 --> 00:06:26.120
101
00:06:26.279 --> 00:06:30.759
102
00:06:30.759 --> 00:06:33.920
103
00:06:34.480 --> 00:06:36.959
104
00:06:37.000 --> 00:06:40.600
105
00:06:40.680 --> 00:06:44.199
106
00:06:44.199 --> 00:06:46.639
107
00:06:46.680 --> 00:06:50.079
108
00:06:50.120 --> 00:06:52.920
109
00:06:53.079 --> 00:06:57.959
110
00:06:58.000 --> 00:07:02.560
111
00:07:03.439 --> 00:07:06.920
112
00:07:07.160 --> 00:07:10.800
113
00:07:10.879 --> 00:07:12.639
114
00:07:19.079 --> 00:07:21.480
115
00:07:21.480 --> 00:07:24.879
116
00:07:25.519 --> 00:07:27.800