June 1, 2025

Sunday 6/1 Bonus: The Rise and Fall of Sean “Diddy” Combs. A biography.

Show Notes
Transcript

With the courtroom on pause, Nate Oliver takes you on a deep, documentary-style journey through the life of Sean “Diddy” Combs. From Harlem tragedy to hip-hop royalty, from Bad Boy’s chart-topping heyday to billion-dollar business moves, Diddy’s story is one of ambition, reinvention, and controversy. But behind the mogul’s empire, witness testimony now paints a chilling portrait of control, violence, and fear. As the trial’s bombshells threaten to rewrite Diddy’s legacy, this special episode traces every triumph, scandal, and turning point—right up to the moment the world waits for a verdict.

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Calarugashark Media. As we take a break in the courtroom

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drama this weekend, let's take a look at the life

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of Sean Diddy Combs, a story that stretches from the

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streets of Harlem, to the heights of global superstardom, and

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now to the center of one of the most sensational

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trials in music history. I'm Nate Oliver and today on

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Did He Do It? We're stepping away from the courthouse

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to bring you a deep dive biography of the man

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at the heart of it all. Shawn John Combs was

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born on November fourth, nineteen sixty nine, in Harlem, New

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York City. His early life was shaped by both promise

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and tragedy. His mother, Janis, was a teacher's assistant and

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part time model, while his father, Melvin, was a US

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Air Force veteran who became entangled in the Harlem drug trade.

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When Shawn was just three, his father was murdered in

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a drug related shooting, a loss that cast a long

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shadow over his chotherchildhood. For years, Janis shielded Sean from

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the truth, telling him his father died in a car accident.

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It wasn't until Seawan was a young man that he

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discovered the real story by searching old newspapers. After Melvin's death,

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Janis moved Shawn and his sister Keisha to Mount Vernon,

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just north of the Bronx. She worked multiple jobs to

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give her children a stable life, instilling in Shawn of

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fierce drive and a sense that nothing would be handed

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to him. At Mount Saint Michael Academy, an all boys

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Catholic school, Shawn earned the nickname Puff because of the

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way he puffed out his chest when he was angry

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or determined. Even as a teenager, he was hustling selling newspapers,

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running a paper route, and organizing neighborhood parties. In nineteen

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eighty seven, Shawn enrolled at Howard University in Washington, d c.

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Majoring in business, but the call of music was too strong.

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He threw legendary parties, made connections, and began to see

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the power of hip hop culture up close. After just

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two years, he dropped out and returned to New York,

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determined to break into the music industry. His first big

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break came as an unpaid intern at Uptown Records, a

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label that was helping to define the sound of R

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and B and hip hop. In the early nineteen nineties,

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Shawn's work ethic was legendary. He'd sleep in the office,

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fetch coffee, and do whatever it took to get noticed.

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He quickly rose to talent director, working with acts like

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Jodasee and Mary J. Blige. He had a knack for

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spotting talent and shaping artists' images, blending street wise authenticity

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with crossover appeal. But Shawn's ambition sometimes clashed with Uptown's

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founder Andre Harrell. In nineteen ninety three, after a series

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of creative disagreements, Shawn was fired. He was devastated, but

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also liberated. That same year, he launched bad Boy Entertainment,

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partnering with Clive Davis. His first signing would change hip

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hop forever. A Brooklyn rapper named Christopher wall Ellis, better

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known as the Notorious Big bad Boy, exploded onto the

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scene with Biggie's debut album, Ready to Die in nineteen

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ninety four. The album was a critical and commercial smash,

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and Shawn's production style, sampling soul classics, layering lush beats,

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and adding cinematic flare, became the new blueprint for hip hop.

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He built a stable of stars, Faith Evans, one twelve Mays,

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The Locks and more songs like Craig Mack's Flavor and

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ya Ear and Biggie's Juicy became anthems, and Shawn's reputation

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as a hit maker was sealed. But success came with turmoil.

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The East Coast West Coast rap feud, fueled by media

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hype and real life grudges, turned deadly after Tupac Shakur

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was murdered in nineteen ninety six, Biggie was killed in

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a drive by shooting just six months later. Shawn was shattered.

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He poured his grief into music, recording I'll Be Missing

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You with Faith Evans in one twelve, a tribute to

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Biggie that sampled Sting's Every Breath You takee. The song

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topped charts around the world and won a Grammy, cementing

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Sean's status as hip hop's most resilient kingmaker. As the

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nineties turned into the two thousands, Sean Combs, now calling

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himself Puff Daddy, then p Didty, and eventually Just Didty,

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expanded his empire far beyond music. In nineteen ninety eight,

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he launched Sean John, a luxury streetwear brand that brought

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hip hop style to the runways of Paris and Milan.

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The brand won the CFDA Menswear Designer of the Year

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Award in two thousand and four, making Sewan the first

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African American designer to receive the honor. Diddy's business acumen

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was legendary. He partnered with Diego in two thousand and

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seven to revive Sarrok Vodka, using his marketing genius to

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turn a struggling brand into a two billion dollar juggernaut.

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He invested in Aqua Hydrate Water with Mark Wahlberg, launched

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the Revolt TV network to empower black creators, and continued

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to shape the sound of hip hop with new artists

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and collaborations. By the twenty tens, Shawn Combs was one

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of the wealthiest and most influential figures in music, A

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mogul with a net worth approaching a billion dollars. He

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was everywhere producing reality shows like Making the Band, starring

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in movies like Monster's Ball and Get Him to the Greek,

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and making headlines for his lavish parties, high profile romances,

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and relentless hustle. But behind the glitz and glamour, there

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were whispers of a darker side. Stories circulated about Ditty's temper,

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his controlling nature, and the intense loyalty he demanded from

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those around him. Some called him a genius, others called

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him a tyrant. He was known for rewarding those who

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delivered and cutting off those who crossed him. In two

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thousand and five, a nineteen year old singer named Cassie

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Ventura signed to Bad Boy Records. Cassie was beautiful, talented,

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and quickly became Ditty's muse and eventually his girlfriend. Their

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relationship was the subject of endlas speculation in the tabloids,

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but few knew what was really happening behind closed doors.

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Over the next decade, Cassie's career flourished and then stalled.

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She released hits like Me and You, modeled for major brands,

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and starred in movies, But, as she would later reveal,

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her relationship with Ditty was marked by control, volatility, and abuse.

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In a twenty twenty three lawsuit, Cassie alleged that Ditty

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beat her, forced her to participate in drug fueled freak

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offs with male escorts, and threatened to release explicit tapes

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if she ever tried to leave. The suit was settled

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for twenty million dollars, but it opened the floodgates for

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further investigation. Federal prosecutors began digging into Ditty's world. In

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September twenty twenty four, he was arrested on federal charges

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of racketeering, sex trafficking, and transportation for prostitution. The indictment

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alleged a pattern of coercion, intimidation, and violence stretching back decades.

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The trial that followed would bring together a cast of

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characters from every chapter of Ditty's career. Cassie took the

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stand as the prosecution's star witness, describing a relationship defined

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by violence, humiliation, and fear. She told the jury about

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being beaten, choked, and urinated on about being forced into

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freak offs with strangers, while Ditty watched and filmed about

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blackmail threats and a brutal twenty sixteen beating in a

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Los Angeles hotel hallway, an incident caught on security camera

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and later settled for ten million dollars with the hotel.

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Kid Cuddy, the Grammy winning rapper and actor, also testified.

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He described a brief romance with Cassie in twenty eleven

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that turned dangerous when Ditty found out. Cutty told the

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jury about Ditty breaking into his Hollywood Hills home, unwrapping

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his family's Christmas presence, and repositioning his security cameras. Weeks later,

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Cutty's Porsche was destroyed in a fire bombing. He told

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the court he believed Ditty was behind them arson, though

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Ditty denied it. When they confronted each other in a

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Los Angeles hotel years later, Ditty unexpectedly apologized. After the apology,

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I found peace with it, Cuddy said. Dawn Richard, a

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former member of Danity Kane, painted a picture of Ditty

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as both mentor and monster. She described witnessing Ditty beat

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Cassie with a skillet, drag her by her hair, and

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threaten her with violence. Capricorn Clark, Ditty's former executive assistant,

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told the jury about being kidnapped at gunpoint by Ditty,

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forced to act as a go between in a confrontation

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with kid Cuddy and watching in horror as Ditty kicked

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Cassie in a jealous rage more in a moment. The

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prosecution's case was bolstered by a parade of former employees,

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friends and insiders. Deontae Nash, Cassie's stylist, described Ditty's obsessive

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control over Cassie's life, dictating her clothing, hair, and even

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threatening to have her parents fired if she defied him.

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Nash recounted a night when Ditty beat Cassie so badly

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that she needed stitches above her eyebrow, and Nash and

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another aid tried to intervene, but were thrown off. Look

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what y'all made me do, Ditty allegedly said afterward. Mia,

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a former employee who testified under a pseudonym, described years

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of sexual assault, sleep deprivation, and psychological torment. She told

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the jury about being forced to work grueling hours without breaks,

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being pressured to use ketamine to stay awake, and being

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threatened with financial and reputational ruin if she ever spoke out.

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You don't just leave Puff, You're trapped, she said. The

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trial also revealed the extent of Ditty's paranoia and need

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for control. Homeland security raids on his homes uncovered AR

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fifteen's with defaced serial numbers, a loaded handgun, a trove

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of pills and powders, and sex paraphernalia, alongside baby oil,

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lingerie and platform heels. Agents found three cell phones hidden

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in a Balenciaga boot, and digital evidence showed a pattern

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of surveillance, blackmail, and intimidation. As the trial played out,

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the hip hop community watched in shock and disbelief. Some

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former collaborators, like Aubrey Odey and Deontae Nash, described a

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culture of fear at Bad Boy, where loyalty was enforced

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through NDAs and threats. Others defended Ditty, insisting his relationships

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were unconventional but consensual. Meanwhile, Ditty's business empire began to unravel.

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Revolt TV and Sea Rock Vodka distanced themselves from the scandal.

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Streaming platforms quietly removed his music. His once glittering reputation

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was in freefall, and his legacy as hip hop's first

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billionaire was overshadowed by allegations of predation and abuse. For decades,

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Sean Ditty Combs was the embodiment of the American dream,

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a kid from Harlem who hustled his way to the top,

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changed the sound of music and built an empire. He

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was a mogul, a mentor, a fashion icon, and a kingmaker.

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But as the courtroom drama continues the world is forced

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to reckon with a darker narrative, a man who, according

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to dozens of witnesses, traded humanity for power, and whose

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empire was built not just on talent and ambition, but

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on fear, secrecy, and control. As we await the next

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chapter in this extraordinary trial, the question remains will did

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he be remembered as a musical visionary or as the

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central figure in one of the most shocking scandals in

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entertainment history. Only time and the jury will tell. We'll

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be back outside the courthouse on Monday, ready to bring

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you every new revelation, every legal twist, and every rumor

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as the ditty trial continues. I'm Nate Oliver, and this

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is did he do it?