June 18, 2025
Wednesday 6/18 Day 33. “Not Isolated Incidents” — The Prosecution’s Final Bombshells and a Trial on Edge
As the prosecution nears its dramatic close, jurors witness the most explicit “freak-off” videos yet—footage that matches weeks of harrowing testimony from Jane, Cassie Ventura, and others. With digital trails, encrypted messages, and financial records tying Diddy and his staff to a web of abuse, the courtroom is gripped by tension and emotional testimony. Outside, the media circus and dueling crowds underscore the trial’s cultural weight. Nate Oliver unpacks every revelation, every strategy, and every moment that could decide Diddy’s fate as the defense prepares to take the stage in America’s most-watched trial.
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WEBVTT
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Warning. This episode contains references to sexual situations that may
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be disturbing to some listeners. Please proceed with caution.
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Callarogas Shark Media. Welcome back to Did He Do It?
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The Daily podcast bringing you every raw, unfiltered detail from
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the Sean Ditty Comb's sex trafficking and racketeering trial. I'm
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Nate Oliver outside the Manhattan Federal Courthouse on Wednesday morning,
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June eighteenth, after a Tuesday in court that delivered some
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of the most explicit, revealing, and consequential testimony yet. Tuesday's
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session saw the prosecution continue its high stakes strategy, presenting
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more graphic freak off videos seized from Ditty's own devices.
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Jurors watched scenes that directly matched the harrowing accounts given
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by Jane Cassie Ventur and other accusers, lavish hotel suites,
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cash handoffs, and Ditty orchestrating marathon drug fueled sex parties
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with multiple women and male escorts. The videos were so
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explicit that the public and media were barred from the courtroom,
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leaving only the jury, judge, attorneys, and Ditty to witness
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the footage. As each clip played, prosecutors paused to highlight
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details corroborated by earlier testimony, the presence of drugs, the
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use of aliases for hotel bookings, and the visible participation
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of Ditty's staff in setting up and managing the encounters.
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Jurors took notes, some shifting uncomfortably, as the prosecution argued
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these were not isolated incidents, but the core of a
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criminal enterprise. Special agent DELIASA. Penland returned to the stand,
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guiding the jury through a digital and financial trail that
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mapped out years of alleged abuse and control. The jury
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reviewed text messages and emails between Ditty, Cassie, and chief
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of staff Christina Korum, arranging travel, hotel rooms, and payments
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for mail escorts and guests, often using coded language and aliases.
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Credit card and bank statements showed bad Boy Entertainment footing
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the bill for flights, luxury hotels, and cash withdrawals that
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lined up with the dates of freak off parties. Travel
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invoices and internal emails matched the testimony of witnesses. Cassie
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booked as Janet Clark and mail escorts like the Punisher
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and Jewels, arriving at the Trump International Hotel at three
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thirty am for pre arranged encounters. Penland emphasized how the
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digital paper trail lined up with the stories told by Jane,
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Cassie and others, reinforcing the prosecution's argument that Ditty's operation
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was deliberate, organized and secretive. Former assistant Jonathan Perez's testimony
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added new layers of detail. Perez described being responsible for
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procuring drugs xanax, cocaine, and molly from contacts known as
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Guido and n Baby Girl, with payments coming from Ditty's
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security team or a signature Gucci pouch that was always
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filled with narcotics and cash. Perez testified that he would
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sometimes deliver thousands in cash to Jane or other guests
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at Ditty's request, and that he was compelled to testify
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under immunity after invoking the Fifth Amendment. The jury saw
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photos of the pouch, and Perez recounted texts where he
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was told to never let the cocaine leave the pouch,
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underscoring the level of control and routine in Ditty's world.
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He also described being instructed to return anything found outside
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the pouch, and that the pouch was a staple during
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every King Knight or freak off. Jurors heard more from
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Cassie Ventura's texts and emails, which prosecutors say document years
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of abuse and threats. In one message, Cassie described being
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dragged by her hair and thrown out of her own
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house by Ditty. Other texts showed her and Ditty coordinating
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freak offs, but prosecutors argued these were the result of
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manipulation and threats, not real consent. Cassie's messages also included
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desperate pleas for help and documentation of Ditty's escalating violence,
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matching her earlier testimony about the psychological and physical toll
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of their relationship, Prosecutors introduced new evidence of alleged witness tampering.
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Call and text logs showed Ditty's bodyguard, Damian d rock Butler,
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repeatedly reaching out to Mia, a former assistant, after Cassie's
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lawsuit became public. Mia testified that these overtures, including offers
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of gifts and requests to meet, left her terrified and
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feeling pressure to stay silent. Prosecutors alleged this was part
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of a broader campaign to intimidate and bribe witnesses, reinforcing
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the racketeering charge. The defense continued to argue that Ditty's
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world was wild, but consensual, not criminal. They highlighted messages
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where Cassie and Ditty coordinated freak offs together, suggesting she
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was a willing participant. Defense attorney Tenny Garag pressed witnesses
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on whether Ditty's staff actually handled drugs or if these
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were private arrangements between adults, and argued that many payments
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could be interpreted as gifts, not trafficking. Judge Aarin Subermanian
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reaffirmed his decision to dismiss a juror who had provided
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inconsistent information about his residency, despite objections from the defense
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about jury diversity. The judge also repeated warnings to Ditty
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about courtroom conduct after prosecutors raised concerns about his reactions
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and attempts to engage the jury. As the afternoon war on,
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the prosecution continued to build its case with a series
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of smaller but significant revelations that seemed to ripple through
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the courtroom. One moment that stood out came when Special
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Agent Penland reviewed a set of encrypted messages between Ditty
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and his chief of staff, Christina Korum. In these exchanges,
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Didty used coded language to discuss entertainment logistics for upcoming
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trips to Miami in Las Vegas, phrases that, according to Penland,
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matched up with the dates and locations of several freak
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off parties described by Jane and Cassie. The jury listened
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closely as Penland explained how investigators used metadata and location
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data from phones and hotel Wi Fi logs to place Ditty,
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his staff, and the escorts at the same hotels on
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the same nights. The prosecution also introduced a series of
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wire transfer receipts and venmo transactions, many of which were
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split into smaller amounts and sent to aliases or shell accounts.
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These payments, Penland testified, were often made within hours of
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the parties and matched the amounts described in earlier testimony
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two five hundred dollars here, five thousand dollars there, sometimes
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marked only with emojis or vague references like for the fun.
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The prosecution argued that this pattern of payments, combined with
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the explicit videos and messages, left little doubt that these
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were not consensual liaisons, but carefully orchestrated acts of trafficking
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and control. The courtroom atmosphere was thick with tension as
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Perez was recalled for a brief but revealing follow up,
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he described how after particularly wild King Knights, he would
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be tasked with cleaning up the aftermath, disposing of used condoms,
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empty pill bottles, and sometimes broken glass or furniture. Perez
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recalled one occasion when he found Jane curled up in
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a guest bathroom, shivering and barely responsive after a marathon
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session that had started the previous evening. He said he
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offered her water and tried to help her to her feet,
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but she waved him away, whispering just let me be.
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Perez's voice broke slightly as he admitted he never reported
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what he saw, fearing for his job and his own
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safety more in a moment. Meanwhile, outside the courthouse, the
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spectacle continued to grow. By late after noon, the plaza
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was packed with a mix of supporters, protesters, and media crews.
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Some chanted for justice for survivors, holding up signs with
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Cassie's and Jane's names, while others waived banners declaring Ditty's
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innocence and warning against what they called a celebrity witch hunt.
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The media presence was overwhelming, with satellite trucks parked along
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the block and reporters broadcasting live updates for networks around
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the world. Vendors hawked t shirts and buttons, and a
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few opportunistic street performers drew crowds with Ditty inspired dance routines,
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adding an almost surreal layer to the day's gravity. Back inside,
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the defense team huddled frequently passing notes and whispering strategy.
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As the prosecution's evidence piled up. Ditty himself sat mostly still,
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occasionally glancing at the jury or jotting down notes for
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his attorneys. At one point, he was seen shaking his
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head and mouthing words to his lead counsel, clearly frustrated
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by the relentless drumbeat of testimony and evidence. As the
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day he drew to a close, Judge Supermanian reminded the
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jury of their duty to weigh all evidence impartially and
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not to let the spectacle outside influence their deliberations. He
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also cautioned the public and media to respect the privacy
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of witnesses and jurors, warning that any attempts at intimidation
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or interference would be met with severe consequences. With the
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prosecution expected to rest as soon as today, the defense
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is bracing to take the spotlight Their strategy, sources say,
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will be to challenge the reliability of the videos and
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digital records, question the motives of key witnesses, and argue
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that the government is criminalizing consensual adult relationships. They are
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expected to call former bad Boy executives, security staff, and
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character witnesses who will testify about Ditty's generosity, the consensual
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nature of his relationships, and the pressures of fame. As
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the city buzzes with anticipation, the stakes for Ditty and
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for everyone whose lives have been touched by this case
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could not be higher. If convicted, did He faces the
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possibility of life in prison and the collapse of his empire.
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For the accusers, this trial is about more than justice.
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It's about reclaiming their stories and shining a light on
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the machinery of power, silence, and survival in the world
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of celebrity. That's where we stand after another day of
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bombshell videos, digital paper trails, and legal brinkmanship. I'll be
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back tomorrow with every new twist, every legal battle, and
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every rumor from inside and outside the courthouse. I'm Nate Oliver,
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and this is Did He Do It?
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This episode of Did He Did He Do It? Was
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produced by Mark Francis and John McDermott for Caalaroga Shark Media.
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Some AI production assistants may have been used
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00:07:28.720 --> 00:07:30.800
111
00:07:31.560 --> 00:07:34.720
112
00:07:36.240 --> 00:07:39.279
113
00:07:39.279 --> 00:07:41.680
114
00:07:41.759 --> 00:07:57.000
115
00:07:57.040 --> 00:08:00.759
116
00:08:00.839 --> 00:08:04.360
117
00:08:05.000 --> 00:08:08.279
118
00:08:08.399 --> 00:08:12.439
119
00:08:12.480 --> 00:08:16.079
120
00:08:17.000 --> 00:08:20.639
121
00:08:20.680 --> 00:08:23.839
122
00:08:23.879 --> 00:08:28.079
123
00:08:28.079 --> 00:08:32.240
124
00:08:32.720 --> 00:08:37.639
125
00:08:37.759 --> 00:08:41.440
126
00:08:41.480 --> 00:08:46.360
127
00:08:46.559 --> 00:08:49.320
128
00:08:49.360 --> 00:08:52.120
129
00:08:52.200 --> 00:08:55.720
130
00:08:55.759 --> 00:08:59.759
131
00:08:59.840 --> 00:09:02.879
132
00:09:02.919 --> 00:09:06.320
133
00:09:06.360 --> 00:09:10.960
134
00:09:11.000 --> 00:09:13.799
135
00:09:13.840 --> 00:09:17.440
136
00:09:17.759 --> 00:09:22.480
137
00:09:22.480 --> 00:09:25.720
138
00:09:25.799 --> 00:09:29.840
139
00:09:30.200 --> 00:09:32.720
140
00:09:32.759 --> 00:09:37.519
141
00:09:37.559 --> 00:09:41.679
142
00:09:41.720 --> 00:09:45.000
143
00:09:45.120 --> 00:09:49.399
144
00:09:49.480 --> 00:09:53.600
145
00:09:53.639 --> 00:09:57.279
146
00:09:57.360 --> 00:09:59.879
147
00:10:00.519 --> 00:10:04.480
148
00:10:04.519 --> 00:10:07.799
149
00:10:08.639 --> 00:10:11.720
150
00:10:12.200 --> 00:10:14.879
151
00:10:14.919 --> 00:10:18.480
152
00:10:18.519 --> 00:10:21.840
153
00:10:21.879 --> 00:10:26.480
154
00:10:26.559 --> 00:10:29.759
155
00:10:29.919 --> 00:10:34.360
156
00:10:34.600 --> 00:10:35.840
157
00:10:40.600 --> 00:10:42.639
158
00:10:42.639 --> 00:10:46.440
159
00:10:47.039 --> 00:10:49.320