June 8, 2025

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

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.






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 --> 00:00:12.199
be disturbing to some listeners. Please proceed with caution. Callaroga

3
00:00:12.279 --> 00:00:20.920
Shark Media. Welcome back to Did He Do It? The

4
00:00:20.960 --> 00:00:24.839
podcast bringing you every raw, unfiltered detail from the Sean

5
00:00:24.960 --> 00:00:32.000
Diddycomb's sex trafficking and racketeering trial. I'm Nate Oliver, and

6
00:00:32.039 --> 00:00:35.039
with the courtroom doors closed for the weekend, we're using

7
00:00:35.079 --> 00:00:38.399
this break to take you deeper than ever before into

8
00:00:38.439 --> 00:00:41.200
the heart of one of the most disturbing and pivotal

9
00:00:41.240 --> 00:00:45.719
aspects of the entire case, the so called freak Off parties.

10
00:00:46.560 --> 00:00:50.799
For weeks, the phrase freak off has echoed through the courtroom,

11
00:00:50.880 --> 00:00:53.600
growing from a salacious rumor into a chilling symbol of

12
00:00:53.640 --> 00:00:58.679
the prosecution's case. Prosecutors alleged these weren't just wild nights.

13
00:00:59.479 --> 00:01:02.719
They were the engine of Ditty's power control, and they

14
00:01:02.840 --> 00:01:07.560
argue his criminal enterprise. Today, we're piecing together how these

15
00:01:07.599 --> 00:01:11.200
parties worked, who was involved, and why they're at the

16
00:01:11.359 --> 00:01:15.040
very center of the government's argument. Let's start with the planning.

17
00:01:15.560 --> 00:01:20.280
According to testimony from Cassie Ventura, former assistants like George

18
00:01:20.319 --> 00:01:25.519
Caplan and even mail escorts, freak offs were never spontaneous.

19
00:01:26.280 --> 00:01:29.959
They were meticulously orchestrated, with a level of detail that

20
00:01:30.079 --> 00:01:36.319
rivals any Hollywood production. Assistants would receive explicit instructions book

21
00:01:36.319 --> 00:01:40.120
a suite, usually at a luxury hotel, under an alias

22
00:01:40.239 --> 00:01:44.200
like Frank Black or Jackie Starr. The room had to

23
00:01:44.239 --> 00:01:47.920
be stripped of identifying details, with connecting suites reserved for

24
00:01:48.040 --> 00:01:53.079
privacy and security. Sometimes entire floors were blocked off and

25
00:01:53.159 --> 00:01:56.159
staff were instructed to avoid the area or if necessary,

26
00:01:56.400 --> 00:02:00.719
to look the other way. George Kaplan, Ditty's former assistant,

27
00:02:01.200 --> 00:02:04.280
described how he'd arrive hours before Ditty and his guests,

28
00:02:04.480 --> 00:02:09.800
setting the stage. Candles were lit and strategically placed. Bottles

29
00:02:09.840 --> 00:02:13.400
of high end alcohol, gatorade, and water were arranged on

30
00:02:13.520 --> 00:02:17.360
every surface. The mini bar was stocked, and party favors

31
00:02:17.800 --> 00:02:21.759
a euphemism for drugs were laid out, sometimes in ornate

32
00:02:21.840 --> 00:02:25.800
bowls or gold plated boxes. Caplan said he'd also lay

33
00:02:25.800 --> 00:02:30.439
out baby oil, sexual lubricant, lingerie, and on occasion, costumes

34
00:02:30.439 --> 00:02:34.520
are props. It was like prepping a movie set, Caplin

35
00:02:34.560 --> 00:02:37.680
told the jury. Everything had to be just right, or

36
00:02:37.680 --> 00:02:41.599
you'd hear about it. Afterward. Caplan would return to clean up.

37
00:02:42.199 --> 00:02:46.719
He described finding broken glass, empty pill bottles, used condoms,

38
00:02:47.240 --> 00:02:51.840
and brown crystallized powder he didn't recognize. Housekeeping Logs from

39
00:02:51.919 --> 00:02:56.000
hotels like Lrmitage, Beverly Hills and the Inner Continental in

40
00:02:56.039 --> 00:03:01.439
Los Angeles documented repeated complaints about candlewax, oil stains, and

41
00:03:01.599 --> 00:03:05.599
rooms left in disarray. One hotel manager testified that Ditty's

42
00:03:05.639 --> 00:03:08.439
rooms were often put out of order for deep cleaning,

43
00:03:08.840 --> 00:03:13.439
with charges for oil damage and biohazard remediation, sometimes running

44
00:03:13.479 --> 00:03:17.479
into the thousands. But the logistics were just the surface.

45
00:03:18.560 --> 00:03:22.439
The real machinery of a freak off was psychological. Cassie

46
00:03:22.479 --> 00:03:26.560
Ventura's testimony was especially wrenching. She described being forced to

47
00:03:26.560 --> 00:03:29.960
participate in these parties, threatened with violence or blackmail if

48
00:03:29.960 --> 00:03:33.719
she refused. Cassie said Ditty would make her have sex

49
00:03:33.759 --> 00:03:37.919
with strangers or male escorts while he watched, filmed, or

50
00:03:37.960 --> 00:03:43.400
directed the action. Sometimes, she said she was given drugs MDMA,

51
00:03:43.800 --> 00:03:47.280
ketamine or cocaine, either handed to her directly or slipped

52
00:03:47.319 --> 00:03:50.400
into her drink. Eventually it became a job for me,

53
00:03:50.479 --> 00:03:53.639
Cassie told the jury, these events consumed my life and

54
00:03:53.719 --> 00:03:58.800
left me exhausted, dehydrated, and emotionally numb. She described how

55
00:03:58.879 --> 00:04:02.000
after a freak off off, she'd sometimes lock herself in

56
00:04:02.039 --> 00:04:04.479
the bathroom and cry or call her mother in the

57
00:04:04.560 --> 00:04:08.960
middle of the night, desperate for comfort. Other witnesses echoed

58
00:04:09.000 --> 00:04:14.000
Cassie's account. Mia, another former assistant, described being forced to

59
00:04:14.000 --> 00:04:17.319
work through the night, sometimes for days on end, making

60
00:04:17.360 --> 00:04:21.040
sure everything was perfect for Ditty's guests. She said she

61
00:04:21.160 --> 00:04:23.879
was pressured to take stimulants to stay awake, and was

62
00:04:23.959 --> 00:04:26.959
threatened with being fired or blacklisted if she ever spoke out.

63
00:04:28.319 --> 00:04:31.959
Mia recalled seeing Cassie hide from Ditty at parties, whispering

64
00:04:32.279 --> 00:04:34.680
He's going to kill me, and said that after some

65
00:04:34.839 --> 00:04:39.439
freak offs, Cassie would be left with visible injuries bruises, cuts,

66
00:04:39.560 --> 00:04:41.680
and once a black eye that had to be covered

67
00:04:41.720 --> 00:04:45.959
with makeup before a public appearance. Male escorts, including one

68
00:04:46.000 --> 00:04:49.399
who went by the nickname the Punisher, testified about being

69
00:04:49.439 --> 00:04:53.120
paid thousands of dollars to participate in these events. They

70
00:04:53.160 --> 00:04:57.240
described being given instructions by Ditty or his staff, sometimes

71
00:04:57.240 --> 00:05:01.600
being filmed, and always being told to keep One escort

72
00:05:01.639 --> 00:05:03.959
said he was paid in cash and signed a non

73
00:05:04.040 --> 00:05:08.120
disclosure agreement before ever setting foot in a hotel room.

74
00:05:08.319 --> 00:05:12.720
Another described Ditty as calm, almost clinical, directing the action

75
00:05:12.800 --> 00:05:16.120
from the sidelines and sometimes joining in. It was like

76
00:05:16.160 --> 00:05:19.480
a performance, but there was always this edge, like if

77
00:05:19.480 --> 00:05:23.319
you did something wrong, there'd be consequences. One escort testified

78
00:05:25.199 --> 00:05:28.920
the aftermath of a freak off was often as chaotic

79
00:05:29.000 --> 00:05:33.720
as the event itself. Hotel staff described rooms trashed with candlewax,

80
00:05:33.959 --> 00:05:39.160
broken furniture, and stains that required deep cleaning. Security supervisors

81
00:05:39.199 --> 00:05:42.279
like Eddie Garcia testified about being called to handle complaints

82
00:05:42.399 --> 00:05:46.199
or to erase evidence, sometimes being offered cash or gifts

83
00:05:46.199 --> 00:05:50.079
in exchange for their silence. In one instance, Garcia described

84
00:05:50.120 --> 00:05:52.399
being paid one hundred thousand dollars to hand over the

85
00:05:52.439 --> 00:05:55.639
only copy of a surveillance video showing Ditty assaulting Cassie.

86
00:05:56.040 --> 00:06:00.560
After a particularly violent freak off, garcias that he signed

87
00:06:00.560 --> 00:06:03.560
a non disclosure agreement with a million dollar penalty and

88
00:06:03.600 --> 00:06:07.800
was told by Ditty, don't make any big purchases. Prosecutors

89
00:06:07.800 --> 00:06:10.199
have argued that these parties were not just about sex,

90
00:06:10.560 --> 00:06:15.839
they were about power. By orchestrating freak offs, Didty allegedly

91
00:06:15.879 --> 00:06:19.600
maintained control over his partners and employees using the threat

92
00:06:19.639 --> 00:06:23.800
of exposure, violence, or financial ruin to keep everyone in line.

93
00:06:23.839 --> 00:06:28.680
Witnesses described a culture of silence enforced by non disclosure agreements,

94
00:06:28.959 --> 00:06:32.600
cash payments, and the ever present fear that crossing Ditty

95
00:06:32.639 --> 00:06:37.079
would mean losing everything. Cassie's mother testified about wiring twenty

96
00:06:37.160 --> 00:06:40.800
thousand dollars to Ditty after he threatened to release explicit

97
00:06:40.920 --> 00:06:44.319
videos of her daughter, calling it the price of keeping

98
00:06:44.399 --> 00:06:48.959
Cassie safe. Former staff described being required to sign NDA's

99
00:06:49.199 --> 00:06:52.319
so strict that even mentioning Ditty's name in public could

100
00:06:52.360 --> 00:07:06.720
trigger a lawsuit more in a moment, the psychological toll

101
00:07:06.839 --> 00:07:10.560
was immense. Mia described how after years of working for Ditty,

102
00:07:10.800 --> 00:07:15.600
she developed PTSD, panic attacks and insomnia. She said she

103
00:07:15.639 --> 00:07:18.439
still jumps when she hears certain songs or smells baby oil.

104
00:07:19.240 --> 00:07:22.600
Cassie testified that she lost her sense of self, describing

105
00:07:22.600 --> 00:07:25.680
how she became a shell of the person she once was.

106
00:07:26.959 --> 00:07:29.319
You start to believe you deserve it, She told the

107
00:07:29.399 --> 00:07:34.199
jury that you're not worth saving. The defense, for its part,

108
00:07:34.319 --> 00:07:38.439
insists that the freak offs were consensual, that everyone involved

109
00:07:38.480 --> 00:07:41.319
was an adult, and that Ditty's world was wild but

110
00:07:41.399 --> 00:07:45.600
not criminal. They've pointed to social media posts and interviews

111
00:07:45.639 --> 00:07:48.839
in which some witnesses described Ditty as generous or the

112
00:07:48.879 --> 00:07:52.399
life of the party, But as more testimony piles up,

113
00:07:52.879 --> 00:07:56.279
the prosecution's portrait of the freakof machine has become harder

114
00:07:56.279 --> 00:08:00.079
to ignore. A world where pleasure, pain, and power were

115
00:08:00.120 --> 00:08:05.199
inextricably linked, and where the price of admission was often secrecy, silence,

116
00:08:05.480 --> 00:08:10.759
and survival. Legal experts say the freak Off parties are

117
00:08:10.800 --> 00:08:15.800
central to the prosecution's racketeering case. They're not just salacious details,

118
00:08:15.839 --> 00:08:19.480
their evidence of a pattern, a system, and prosecutors argue

119
00:08:19.480 --> 00:08:22.920
a criminal enterprise built on fear and control. The government

120
00:08:22.959 --> 00:08:28.279
has introduced hotel bills, wire transfers, and digital evidence text messages, emails,

121
00:08:28.319 --> 00:08:33.720
and even encrypted chats showing how assistance coordinated logistics, paid escorts,

122
00:08:33.759 --> 00:08:37.679
and managed the aftermath. One Homeland security agent testified that

123
00:08:37.720 --> 00:08:41.039
the proximity of weapons, drugs, and sex supplies in Ditty's

124
00:08:41.039 --> 00:08:45.240
Miami mansion was consistent with a high level operation, not

125
00:08:45.360 --> 00:08:49.759
just a celebrity's eccentric lifestyle. As the trial moves forward,

126
00:08:49.840 --> 00:08:52.360
the freak Off parties remain at the center of the

127
00:08:52.360 --> 00:08:56.799
government's case. They're not just about what happened behind closed doors.

128
00:08:57.480 --> 00:09:00.720
They're about how power is wielded, how PSI is bought,

129
00:09:00.720 --> 00:09:04.559
and how sometimes the truth finally comes to light. That's

130
00:09:04.600 --> 00:09:06.960
our deep dive for today. When court resumes, will be

131
00:09:07.039 --> 00:09:10.279
right back with every new revelation, every legal twist, and

132
00:09:10.399 --> 00:09:14.360
every rumor from inside and outside the courthouse. I'm Nate Oliver,

133
00:09:14.519 --> 00:09:19.720
and this is did He Do It? This episode of

134
00:09:19.720 --> 00:09:21.799
Did He Did He Do It? Was produced by Mark

135
00:09:21.840 --> 00:09:25.960
Francis and John McDermott for Calaroga Shark Media. Some AI

136
00:09:26.039 --> 00:09:27.720
production assistants may have been used.