The Evolution of Sean 'Diddy' Combs: Name Changes, Legal Battles, Personal Turmoil, and Triumphs

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Sean ‘Diddy’ Combs. Gregg DeGuire/Getty Images for The Recording Academy

Sean “Diddy” Combs has experienced many challenges and successes in both his professional and personal life.

Diddy started his career in the 1990s as an intern at Uptown Records, leaving Howard University to pursue his passion. He climbed the ranks to become a talent director at the record label, where he played a key role in the development of artists like Jodeci and Mary J. Blige.

After being fired from the label in 1993, he took a bold step to start his own label, Bad Boy Records. He not only boosted his own music career but also helped launch the careers of other top artists like Faith Evans, Machine Gun Kelly, Notorious B.I.G., and more.

Despite his success in business, Diddy also encountered numerous scandals during his time in the spotlight. These controversies ranged from legal issues and assault charges to facing multiple allegations of sexual misconduct.

Keep scrolling to see Diddy’s ups and downs over the years:

1991

In 1993, during his time at Uptown Records, Diddy participated in a charity concert at the City College of New York City alongside Heavy D. Unfortunately, the event was oversold, resulting in a stampede that tragically led to the loss of nine lives. Despite the devastating outcome, no criminal charges were filed in relation to the incident.

After leaving Uptown, Diddy teamed up with Arista Records to establish Bad Boy Records. His initial big artist was Notorious B.I.G., who he moved over from Uptown.

During the same time he started his label, Diddy also became a father for the first time to his son Justin, with his ex Misa Hylton.

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Kim Porter, Sean ‘Diddy’ Combs. Evan Agostini/Getty Images

1994

Diddy began dating Kim Porter and adopted her son Quincy from a previous relationship.

1997

In 1997, Diddy, also known as Puff Daddy, released his first single "Can't Nobody Hold Me Down," which quickly climbed to the number one spot on the Billboard Hot 100 chart. This success led to the release of his debut album, No Way Out. The album featured hit songs like "It's All About the Benjamins," "Been Around the World," "Victory," and the emotional tribute "I'll Be Missing You" dedicated to the late Notorious B.I.G. who tragically passed away earlier that year.

1998

Diddy got his first Grammy win when he took home trophies for Best Rap Album and Best Rap Performance by a Duo or Group for “I’ll Be Missing You.”

The same year he also started his Sean Jean clothing line and welcomed son Christian, who goes by the stage name King Combs, with Porter.

1999

The producer was charged with assaulting Interscope Records executive Steve Stoute, who managed Nas. The pair had a disagreement over Nas’ music video for his song “Hate Me Now,” where Diddy was featured, and Diddy ended up injuring Stoute. Stoute sued Diddy and received a $500,000 out-of-court settlement. Diddy also pleaded guilty to harassment and was sentenced to attend one day of anger management class.

That same year, Diddy also had a brief romance with Jennifer Lopez. While the couple was at a club in New York City, gunfire erupted after Diddy got into an argument with another person at the venue. Diddy was charged with four weapons-related offenses and with bribing his driver, Wardel Fenderson, to take ownership of his gun. The case went to trial and Diddy was acquitted of all charges.

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Dia Dipasupil/Getty Images

2001

In 2001, Diddy made the decision to switch his stage name from Puff Daddy to P. Diddy. Additionally, he terminated Bad Boy's distribution agreement with Arista Records. During this time, Diddy also faced legal trouble when he was arrested for driving with a suspended license in Florida. Fortunately, he was released shortly after on the condition that he would return for a court appearance, as reported by the Associated Press.

2002

In 2002, Sting took legal action against Diddy for using a sample of the Police's song "Every Breath You Take" without permission in the hit track "I'll Be Missing You." Sting emerged victorious in the lawsuit and was awarded 100% of the royalties from the song, with payments expected to continue until 2053.

In 2004, Diddy took charge of the MTV version of Making the Band. This show was originally overseen by Lou Pearlman during its first season on ABC. Diddy played a key role in putting together groups like Da Band, Danity Kane, Day 26, and Donnie Klang.

Diddy performed at the Super Bowl XXXVIII half-time show.

2005

Four years after his first name change, Diddy announced he was no longer going by P. Diddy and would be known as Diddy from then on.

2006

Porter and Diddy welcomed twins D’Lila and Jessie into their family. Just five months before Porter gave birth, Diddy also became a father to daughter Chance with his ex, Sarah Chapman. He made sure to take legal responsibility for his daughter the next year. Unfortunately, Porter and Diddy ended their relationship shortly after that.

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Cassie and Sean ‘Diddy’ Combs. Kevin Mazur/Getty Images for Roc Nation

2007

Following his breakup from Porter, Diddy began dating Cassie (real name Casandra Ventura), who was signed to his record label.

2015

Diddy was arrested for aggravated assault after an altercation with his son’s football coach at UCLA. The charges were later dropped due to lack of evidence.

2017

Diddy announced that he would now be going by the name Love. Five years later, Diddy clarified that he would still use the stage name Diddy but his legal name was now Sean Love Combs.

2018

Porter passed away from pneumonia when she was 47 years old. Even though they had broken up, Diddy and Porter remained close. Diddy gave a heartfelt speech at her funeral, expressing his deep emotions.

During the eulogy, Diddy shared, "She was more than just my partner. She was my closest companion and my source of guidance. Her love was overwhelming for me. It was a lot to process and accept, but I am grateful for the time we shared."

That same year, Diddy and Cassie called it quits after 11 years of dating.

2022

Diddy welcomed daughter, Love, with Dana Tran, making him a father of seven.

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John Lamparski/WireImage

2023

In November 2023, Cassie took legal action against Diddy, accusing him of rape, sex trafficking, and physical abuse. Diddy has denied these accusations.

Diddy's lawyer, Ben Brafman, stated to the New York Times, "Mr. Combs strongly denies these offensive claims. Over the last six months, Ms. Ventura has been pressuring Mr. Combs for $30 million, threatening to write a damaging book about their relationship if he did not comply. This demand was clearly seen as a form of blackmail." Despite retracting her initial threat, Cassie has now chosen to file a lawsuit filled with unfounded and extreme falsehoods in an attempt to damage Mr. Combs's reputation and secure a financial gain.

Shortly after the lawsuit was filed, a settlement was reached. Following Cassie's legal action, additional individuals came forward with similar claims. Joi Dickerson-Neal and music producer Rodney “Lil Rod” Jones both accused Diddy of sexual assault. Diddy has strongly denied these allegations.

The rapper expressed his frustration in December 2023, stating, "Enough is enough." He mentioned that he had been silently observing people trying to tarnish his character and legacy with false allegations in recent weeks, made by individuals seeking financial gain.

Due to the allegations, Diddy made the decision to step down as the chairman of his music television network Revolt.

2024

Diddy’s homes in Los Angeles and Miami were raided by the Department of Homeland Security in connection with a federal sex trafficking investigation.

Homeland Security Investigations (HSI) New York carried out law enforcement operations today as part of an ongoing investigation, with support from HSI Los Angeles, HSI Miami, and local law enforcement partners. "We will share more details as they come to light," Homeland Security stated in a message to Us in March 2024.

During the operation in Los Angeles, TMZ reported that his sons, Justin and King, were detained at the location.

Shortly after the raid, the man accused of being a drug mule for Diddy was arrested for possessing cocaine and marijuana, according to arrest records obtained by Rolling Stone.

In May 2024, CNN revealed security footage from 2016 showing Diddy physically assaulting Cassie. Following the widespread attention the clip garnered, Diddy issued an apology on social media.

"It's important to confront the difficult moments in life, even the darkest ones," Diddy shared in a video on Instagram. "I was struggling. I hit rock bottom, but I'm not making excuses. My behavior in that video was unacceptable. I take full responsibility for my actions and I am truly disgusted."

Just a week later, Diddy faced allegations of sexual assault from model Crystal McKinney in a new lawsuit. According to documents from TMZ, the model claimed that after meeting in 2003, Diddy drugged her and forced her to engage in sexual acts against her will.

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