Cassie, singer and ex-girlfriend, at center of testimony

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Casandra “Cassie” Ventura Fine is starting another chapter of her life.

“I am better today, but I will always be recovering from my past,” she wrote in a lengthy letter to fans last year.

The Instagram note was posted days after security footage surfaced, showing her then-boyfriend Sean “Diddy” Combs kicking, hitting and beating her at a now-shuttered Los Angeles luxury hotel in 2016. Combs, the music producer-turned-Hollywood power player, was later charged with sex crimes after his September arrest in Manhattan. 

Now, with Combs’ federal trial underway, Cassie is central to prosecutors’ case against the Billboard chart-topper turned disgraced former billionaire.

Their entangled legal saga first began in November 2023 when Ventura filed a bombshell civil lawsuit against her A-list ex-boyfriend, claiming rape and years of physical abuse. The two settled the suit one day later. 

Known for the hit track “Me & U,” the lead single off her self-titled (and only) studio album, the singer is set to testify in court as one of Combs’ alleged victims, accusing Combs of coercing her into sex and physically beating her.

In court May 12, Assistant U.S. Attorney Emily Johnson described one instance in 2009 where Combs allegedly threw Cassie on the floor of an SUV and “stomped repeatedly on her face.” Cassie will testify about another instance when she said Combs forced an escort to urinate in her mouth, Johnson said.

Combs’ defense, however, argued that Cassie became jealous when she realized she would never be the music mogul’s wife. “Regret does not mean coerced,” said Combs’ lawyer Teny Geragos, attempting to poke holes in one of the prosecution’s arguments.

How long was Cassie with Diddy? They met when she was 19 – and he was 37

At 19, Cassie met a then-37-year-old Combs in 2005 and signed to his music label Bad Boy Records the following February.

In her 2023 suit, Cassie’s legal team claims that “within two years of meeting Mr. Combs, Ms. Ventura found herself lured into the immediate circle of her boss, the owner of her record label, and one of the most powerful men in the entertainment industry.”

From there, a decadelong relationship formed by unwanted force and control allegedly began.

Though Cassie’s parents were “skeptical of (his) displays of wealth,” Combs began renting apartments for the early career entertainer around 2008 or 2009 in Manhattan near his own New York City residence, the suit claimed. Around 2010, Combs began paying for an apartment in Los Angeles near his own home in the sprawling California city.

Then, to maintain control and order over her life, he allegedly plied the music up-and-comer with prescription drugs. He also “violently beat” her, according to Cassie’s lawsuit, forcing her to stay in hotel rooms while bruises on her body healed.

According to her suit, Combs also forced her to participate in “freak offs,” drug-fueled parties with male sex workers conducted without Cassie’s consent.

What allegedly happened between Cassie Ventura, Diddy

In 2015, Combs’ alleged behavior intensified. During a surprise birthday dinner for Cassie’s 29th birthday, Combs forced her to participate in a “freak off,” Cassie claimed.

Combs allegedly went back to a hotel room where Cassie’s friends were and dangled fashion designer Bryana “Bana” Bongolan over the 17th floor balcony of the hotel suite. Cassie’s friend Tiffany Red posted a carousel of selfies on Instagram in November, recalling the date of the alleged 2015 assault. Red captioned the post, “seventeen stories up high on 9/7/15 with the homies.”

And in 2016, an event central to the case against Combs took place.

A surveillance video reportedly from the since-closed InterContinental Hotel in Los Angeles on March 5, 2016, surfaced last year in reports from CNN. Diddy, clad in a bath towel, runs down a hotel hallway toward Ventura. In the footage, he strikes her, throws her to the ground and kicks her twice. Then, he grabs her and drags her down the hallway. The video also shows Diddy throwing what appears to be a vase.

The video appears to corroborate what’s alleged in Cassie’s suit. Diddy apologized in an Instagram video prior to his arrest, saying he was “disgusted” with his actions, though his legal team pushed back against the video’s inclusion during the trial. (In a pre-trial hearing April 25, lawyers for Combs entered a motion to exclude a 2016 surveillance video obtained by CNN from evidence used in the trial. But Judge Arun Subramanian denied their request, saying the video was a “fair and accurate” depiction, and that there are two witnesses who authenticated the tape.)

By September 2018, at a dinner at an Italian restaurant in Malibu, California, Cassie claimed she hoped to end their relationship. After dinner, Combs allegedly forced his way into her apartment and raped her. The next year, in 2019, she entered contracts to end her business relationship with Combs and married trainer Alex Fine.

On May 12, Fine was spotted at the courthouse as opening arguments got underway in Combs’ trial.

Cassie Ventura kids: Singer is pregnant with her third child

Almost two years after Cassie’s bombshell lawsuit, Combs is now standing trial on federal sex-crimes charges.

In the half-decade since walking away from Combs, Cassie “struggled with the physical and mental manifestations of her trauma,” according to her lawsuit. “The birth of her two children, however, allowed her a new lease on life and gave her purpose.”

Cassie and Fine welcomed two daughters: Frankie, 6, born in December 2019, and 4-year-old Sunny in March 2021.

“She credits her children with saving her from the trauma that had consumed over a decade of her life,” the suit from 2023 reads.

Then, on Feb. 19, Cassie announced on Instagram that she was pregnant again with her third child.

After “Me & U” and Cassie and Diddy, there’s now the future: testifying on the witness stand and awaiting a verdict.

Contributing: Edward Segarra, Anna Kaufman, Anika Reed

If you are a victim of domestic violence, The National Domestic Violence Hotline (thehotline.orgallows you to speak confidentially with trained advocates online or by the phone, which they recommend for those who think their online activity is being monitored by their abuser (800-799-7233). They can help survivors develop a plan to achieve safety for themselves and their children.

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