Diddy Trial: Chart Cataloguing 71 Potential Freak Offs Reveals Conflict at the Heart of the Case

A chart summarizing a bunch of data, argued over and gone through in line-by-line detail, may not sound very exciting. But such a chart was at the center of Sean "Diddy" Combs' federal sex trafficking and racketeering trial for a day and a half this week, and how it was used by each side ended up revealing a great deal about how they see the case.

Government Exhibit 1402 contained no new information. Instead, it was a chart — a summary of details the government had culled about 71 potential meetings between 2009 and 2017. Those possible meetings involved people — mostly Diddy, former girlfriend and alleged victim Cassie Ventura, and a number of escorts — in hotels or private residences in a number of cities including New York, Los Angeles, and Miami.

The charts pointed to underlying evidence like texts, flight records, and credit card bills to show when these meetings may have taken place, where, who was likely there, and if any of the participants had flown there on Combs' dime — as was the case in 20 out of the 71 possible meetings.

The implication, of course, is that all of these potential meetings (in only a few cases where there was video evidence could the meetings actually be confirmed) were freak offs, the sometimes days-long sessions in which women were allegedly directed by Combs to have sex with escorts while he watched.

Special Agent DeLeassa Penland of the Southern District of New York was brought to the witness stand by prosecutor Emily Johnson to talk the jury through exactly what the chart showed.

Penland began by describing the chart, which she said consists of "certain meetings that were attended by certain individuals at certain cities and certain locations," though she admitted that, absent the few instances with video evidence, she couldn't be certain the meetings actually occurred.

She then began breaking down one example of a possible meeting on the chart. The third example on the chronological list showed a potential meeting from December 11 to December 13, 2009 at New York City's London hotel with Diddy, Cassie, and the escort Jules Theodore.

To begin, Johnson showed a text exchange extracted from Diddy's phone between him and Jules on December 7, 2009 discussing details of Jules' travel to New York.

"I'm avail fri through Sunday. Whatever flights are fine," Jules texted to Diddy.

Two days later, Combs texted Jules an itinerary in the escort's name for a round-trip flight from L.A. to New York that left on December 11 (a Friday) and returned on December 13 (a Sunday). There was also a note that he would be transported straight from baggage claim at the airport to the London Hotel.

Johnson then showed an additional, identical copy of Jules' flight itinerary that the government got from Diddy's company Combs Global.

After that, Johnson showed an email written by Diddy on December 8, 2009 to Toni Bias (now Toni Fletcher), who was at the time the personal finance director at Bad Boy Entertainment.

The email read: "Hey, I need a FLT booked for Friday 4:00 p.m. or 3:00 p.m. from LA to NYC, reg room at London Hotel under Jules Theodore, ASAP. Let me know when it's done PLS."

Fletcher responded with a copy of Theodore's flight itinerary, and a confirmation of a reservation at the London Hotel from December 11 to December 14.

Johnson and Penland continued talking through a number of other entries on the list, which all contained a similar amount of detail and underlying evidence. Johnson showed the jury several 30-second excerpts of video of what seemed to be freak offs (people in the gallery and the overflow room could not view the videos), in order to prove that a few of the meetings happened and to demonstrate who was in attendance.

One of the notable details of Penland's testimony was a look at a number of Diddy's monthly American Express bills. When demonstrating the total cost of a particular possible meeting, which was usually thousands of dollars, Penland would show a pie chart demonstrating how big a slice the expense was of the mogul's monthly credit card bill.

The bills were always in the six figure range, anywhere from $218,353 to, in one 2012 example, $944,059. They were paid off every month, from a variety of Combs and Bad Boy-associated bank accounts.

The questioning from Johnson emphasized Combs' complicity in the possible (and sometimes confirmed) freak offs — that he was the one to pay for travel arrangements and lodging, and was the prime mover in making them happen.

The mogul's lawyer Teny Geragos, when cross-examining Penland, seemed to have a different interpretation — that Ventura, the woman in nearly all of the examples on the chart, was an enthusiastic participant in, and sometimes even an initiator of, the experiences.

The attorney primarily used her cross of Penland as a chance to show text exchanges between Diddy and Cassie in the times leading up to or immediately after many of the dates on the chart — messages in which Cassie appeared to express excitement and desire, and sometimes even offered to contact the escorts directly.

"I had fun with you Sunday/Monday," she wrote to Combs in the aftermath of one freak off. Right before another one, she texted Combs, "When do you want to freak off, LOL?" A week after a third freak off, she wrote, "Today I texted you that I wish we could have FO'd before you left."

Geragos also showed portions of what appeared to be freak off videos to the jury, but much longer excerpts than Johnson did. She played a nearly five-minute segment of one video, and a section of a different one that ran for three minutes and fifty seconds.

Johnson, on redirect, made clear that the 71 possible meetings on the chart are not all of the potential freak offs the government has evidence for, just the ones that met the high bar necessary for inclusion on the chart. She also provided a post-freak-off text from Ventura to Combs that painted a very different picture than the messages Geragos had shared just moments before.

"Nothing good comes out of fos anymore," Cassie wrote to Combs in early 2017. "You treat me like you're Ike Turner."