The identity of the individual referred to in waves of dramatic legal filings as Victim-1 — the woman at the very center of the racketeering conspiracy and sex-trafficking case against the music mogul Sean Combs — was never much in question.
But when she takes the witness stand at a Manhattan courthouse under her own name this week, there will be little doubt that there would not have been a criminal indictment against Mr. Combs without the testimony of Casandra Ventura.
A singer and model known mononymously as Cassie, she was Mr. Combs’s on-and-off girlfriend — and employee — almost from the time they met in 2005 (when she was 19, he 37), until she finally severed ties from his storied record label, Bad Boy, in 2019.
After months of preparation and anticipation, Ms. Ventura, now 38, is expected to recount for the jury how Mr. Combs instituted a system of abuse and control over her life and career for more than a decade. Prosecutors say the executive dangled ever-disappearing music opportunities; beat her when she stepped out of line; and plied her with drugs, forcing Ms. Ventura to have marathon sex sessions with male prostitutes while he taped the encounters.
Lawyers for Mr. Combs have portrayed the relationship as loving but deeply toxic and complex, prone to infidelity and mutual abuse, while maintaining that any sexual arrangements were completely consensual. They depict Ms. Ventura as a bitter ex and extortionist who sought only a payday, not justice.
What both sides cannot disagree about is that it was Ms. Ventura’s decision in late 2023, following extensive therapy, to pour her allegations into a federal lawsuit — and Mr. Combs’s choice not to settle the dispute before it became public — that led to this moment, in which Mr. Combs, 55, has fallen from a beloved billionaire celebrity to an inmate facing a potential life sentence.
Though Ms. Ventura’s lawsuit ended with an eight-figure settlement just a day after it became international news, her supernova of a complaint kicked off a cascade of civil lawsuits against Mr. Combs now numbering in the dozens. It also triggered a criminal inquiry that led to an indictment nearly a year later and presented him as the kingpin of a criminal enterprise that sex trafficked women, including Ms. Ventura, torched the car of a romantic rival, and kidnapped or bribed people in a pattern of related crimes dating back to 2004.
The version of events laid out by the government so far in its opening statement on Monday closely mirrored the details and language of Ms. Ventura’s original suit. In it, she sought to implicate a team of subordinates who helped Mr. Combs assert and maintain his dominance over her, including via threats and retribution — for instance, suppressing her music for disobedience — and by helping to conceal his behavior.
When she takes the stand on Tuesday, prosecutors will hope to portray Ms. Ventura as an imperfect but brave truth-teller on a healing journey, hearkening back to the strong women behind the #MeToo-era convictions of Harvey Weinstein, R. Kelly and Bill Cosby. She will be tasked with explaining the context surrounding some of the most explosive pieces of potential evidence — including her would-be memoir and graphic videos of sexual activity and abuse that prosecutors will argue are linked by the web of Mr. Combs’s power and dominance.
The defense will aim to frame Ms. Ventura as a willing and even enthusiastic participant in a troubled, nontraditional romantic arrangement.
“The evidence is going to show you a toxic, dysfunctional relationship between two adults,” a lawyer for Mr. Combs, Teny Geragos, said in her opening argument. “You may think, wow, that is a really bad boyfriend. But the evidence will show you a capable, strong woman, willingly engaged in their relationship.”
Such a central role in the case has pushed Ms. Ventura into a glaring spotlight that had eluded her for most of the last two decades, as she slipped from a blossoming R&B talent to a professional girlfriend and then, a footnote and cautionary tale in the music business.
But instead of leaning into the renewed attention over the last 18 months, she has only receded further, friends and past associates say, refusing all interviews and burrowing deeper into family as she steels herself for what could be a grueling few days on the stand, recalling the darkest chapters of an otherwise charmed life.
And as if the subjects at hand were not knotty enough, there will be an added layer of intrigue in court: When Ms. Ventura re-emerges for a mass audience as the prosecution’s star witness, she will do so well into the third trimester of pregnancy with her third child.
One purpose of Ms. Ventura’s testimony will be to trace how years of alleged subjugation at the hands of Mr. Combs led to her own descent from a once-promising model with top-tier representation, and a burgeoning pop star with a Top 5 hit, to a drug-dependent, struggling artist.
Those who knew her as an ambitious adolescent full of talent and possibility will be following along with interest, eager to answer their own nagging questions about what went wrong.
“She was always going to amount to amazing things in this world,” said Kate Fioravanti, the former arts director at a Connecticut charter school where Ms. Ventura attended middle school.
Born Casandra Elizabeth Ventura in New London, Conn., Cassie was one of 45 children enrolled at the local Interdistrict School for the Arts and Communication, or ISAAC, in its 1997 inaugural class, following six years of Catholic school.
There, she was beloved, Ms. Fioravanti recalled, becoming the school’s first student body president and even composing an original opera, “The Two Faces of Friendship,” at age 12, as part of a program with the Metropolitan Opera to make the form more accessible. (Set in a middle school, the local paper called the show “nearly as compelling as ‘Aida.’”)
A piano player, dancer and top student, Ms. Ventura “was influential, but never demonstrative,” Ms. Fioravanti said. “When she spoke, people listened.” The educator added, “She was universally respected by every single teacher, every single student,” and many expected she would go on to get her doctorate.
Instead, with the support of her parents, Ms. Ventura pursued dance and modeling, signing with the agency Wilhelmina and walking the runway at New York Fashion Week by 16.
“They like the uncertainty of her background,” her mother, Regina, then an administrative assistant at Pfizer, said at the time. “She’s diversity.” (Ms. Ventura’s mother is Black and her father, Rodrick, is Filipino.) She appeared in catalogs for Abercrombie & Fitch, J.C. Penney and Delia’s, stealing naps during commutes, working on homework in between shoots and using the money from her modeling to buy her family a boxer puppy.
“Anyone who thinks it’s glamorous should be here at 3 a.m. Thursday and watch while we get into our cold car and drive to catch the Metro North in New Haven, so we can ride commuter rail to the city,” her mother told a local paper.
After graduating from the Williams School, a Connecticut prep academy where she had scored a dance scholarship, in 2004, Ms. Ventura dreamed of majoring in criminal justice and even joining the C.I.A. But she opted to defer college at Pace University and instead move to New York to continue following her show business dreams.
As a teenager in the city, Ms. Ventura met Ryan Leslie, an up-and-coming singer, producer and songwriter who would kick-start her recording career. After Mr. Leslie introduced her to the music mogul Tommy Mottola, who signed her to his management company, she soon found a new champion in Mr. Combs. He inked her to a 10-album deal with Bad Boy, releasing her debut single, “Me & U,” in 2006.
“We were going to dinner at Cipriani’s to talk about me signing with Bad Boy, and I remember thinking, ‘How am I gonna loosen up?’ I was so nervous. I knew he was going to want me to sing,” Ms. Ventura recalled to The New York Times in 2007. After she sang at the dinner table, “He immediately said: ‘Let’s do this. We have to do this.’”
Soon, Cassie was back at ISAAC as its most famous alum, with a lauded self-titled debut album and a hit that had reached No. 3 on the Billboard singles chart. At the school that molded her, she told students that she was working on a second album, and maybe even a duet with Rihanna, then a fellow rising pop singer.
Neither ever came to fruition.
First a mentor, then a boyfriend
Within a year of signing to Bad Boy, according to Ms. Ventura’s 2023 lawsuit, Mr. Combs, better known as Puff Daddy or Diddy, “became deeply entrenched in Ms. Ventura’s life, almost immediately asserting possession and control over her, and inserting himself into all aspects of her career and her personal life.”
She was framed in the press as the label’s “latest princess,” and as fans speculated about a potential romance between Cassie and the boss nearly two decades her senior, he at first worked as her chief cheerleader and defender. Hyping her up as the next Britney Spears or Janet Jackson, Mr. Combs pushed back in the press after a string of sloppy early performances.
“I’m with her through her development,” he told MTV. “It just made me appreciate that she got nervous, and it was kind of cute to me, to be honest.” Mr. Combs added, “I don’t care how many performances it is, I’m going to be with her until she gets it right.”
Behind the scenes, the lawsuit and federal prosecutors contend, things quickly turned darker as Mr. Combs dangled the possibility of career progression in exchange for Ms. Ventura’s participation in increasingly extreme sexual scenarios, which he called “freak-offs.” (Lawyers for Mr. Combs say that his penchant for “nonconforming sexual activity,” like voyeurism and partner-sharing, make him a “swinger,” not an abuser.)
It was following one of these alleged freak-offs — which the government has described as choreographed, drug-fueled sex marathons that could last for days — that prosecutors say Ms. Ventura attempted to escape a hotel room, only to be brutally beaten and dragged by Mr. Combs in the hallway.
The government plans to present the 2016 incident, which was captured in surveillance footage and later aired by CNN, as key evidence. The defense says the dispute was not related to a freak-off but stemmed from a fight about infidelity by Mr. Combs.
Still, it would be more than two years before Ms. Ventura left Mr. Combs for good. She is expected to testify that, near the end of their relationship in 2018, Mr. Combs forced his way into her home and raped her, echoing her lawsuit.
Ms. Ventura’s career had already faltered. Despite intermittent songs with stars like Lil Wayne and Akon, plus a 2013 mixtape released online, she never put out a proper second album, leaving fans and industry experts alike wondering why.
“In retrospect, it doesn’t seem like she was ever, ever intended to be a big moneymaker for the label,” said Touré, a veteran music journalist who has blogged about the case. Mr. Combs, Touré added, “wasn’t intending to really have her be a serious, real artist. He was stringing her along.”
In late 2018, when Kim Porter, another ex-girlfriend of Mr. Combs’s and the mother of three of his children, died suddenly, Ms. Ventura used the tragedy as a distraction to escape for good. By early 2019, tabloids and gossip blogs were reporting that she was dating Alex Fine, who had previously worked as a personal trainer for her and Mr. Combs.
Lawyers for Mr. Combs have framed that relationship as a betrayal by Ms. Ventura, and will hope to portray the infidelity in the relationship, like the domestic violence, as mutual in their cross-examination of her. Ms. Ventura and Mr. Fine, an actor, model and former pro bull rider, announced they were expecting their first child that June — earning an Instagram congratulations from Mr. Combs — and were married by the director Peter Berg that September. The couple now has two daughters.
In the years since, Ms. Ventura required “intensive therapy and other medical care” to recover from her relationship with Mr. Combs, according to her lawsuit.
As part of that process, she began drafting a memoir about her life and healing, which the defense has subpoenaed as possible evidence and may seek to paint as a tactic to manipulate Mr. Combs into paying her settlement.
Lawyers for Mr. Combs have argued in court papers that the writings “memorialize a version of events that is markedly different from what she has told the government and will testify to at trial,” and have referred to a recorded eight-minute conversation where a former lawyer for Ms. Ventura offers a representative for Mr. Combs the exclusive rights to the book for $30 million.
(While Ms. Ventura’s eventual settlement with Mr. Combs may have included a nondisclosure agreement barring disparagement of one another, private contracts cannot prevent someone from testifying truthfully in criminal proceedings.)
Mr. Combs’s legal team has also indicated it will question Ms. Ventura about explicit videos of sexual encounters in which the defense contends in court papers “she is evidently happy, dominant and completely in control.” (The recordings, taken from Ms. Ventura’s electronic devices that were turned over to law enforcement, could be seen at least in part by the jury.)
“This sex trafficking is a 10-year relationship,” Marc Agnifilo, a lawyer for Mr. Combs, said earlier this year. “These two people were in love. That will be made abundantly clear by the way they speak to each other, by the way other witnesses described their time together, and by the circumstances of how they broke up.”
In the months leading up to her testimony, Ms. Ventura has prepped extensively for what is likely to be an emotionally taxing and combative stretch on the witness stand.
For a time, Ms. Ventura considered using her recently raised profile to begin a comeback as a singer or model. Instead, she opted to ignore the attention swirling and tighten her inner circle, worrying about the case’s effect on her family.
In some of her few public appearances, she has appeared silent and resolute, supporting Mr. Fine at Paris Fashion Week and the London premiere of the television show “MobLand,” in which he appears as an actor.
Anything she has been waiting to say, for years or even decades, will come out first on the witness stand.
“She is capable of so many things, and people have focused on that she’s beautiful and she’s talented,” said Ms. Fioravanti, her former teacher. “But I suspect she is going to impress a lot of people with her incredible intelligence.
“She’s not an activist,” Ms. Fioravanti added, “but she is absolutely someone who will stand up and say, this is what we should be doing, and this is how it should go.”
Kitty Bennett contributed research
