The Evolution of Diddy

Updated 3/26/2024 at 11:00 a.m. ET

The way Sean “Diddy” Combs was continuing his climb up the music legend ladder, several of his properties were raided by the Department of Homeland Security. Why? Suspicions point to the bombshell sexual assault and sex trafficking lawsuits filed against him over the past few months - one from his own ex-girlfriend and music protégé, Cassandra “Cassie” Ventura.

Unfortunately her lawsuit along with many others put the rap mogul through the fire right as he was promoting the release of his new album, The Love Album: Off The Grid. However, despite the album’s nomination, the Recording Academy was forced to reconsider his invitation to the Grammys.

Don’t get it twisted. Diddy’s rise to fame was warranted given the talent he produced and business endeavors he embarked on. However, one can’t help but wonder what he did behind closed doors to achieve and maintain his billionaire status.

Here’s our evolution of Diddy before all hell broke loose.

Sean John Combs was born in Harlem, New York, on November 4, 1969. His mother Janice worked as a teacher; his father Melvin served in the U.S. Air Force. Combs’ father died when he was 3, leading Janice to relocate her family to Mount Vernon in upstate New York. He attended Howard University, where Combs would become known for his legendary parties. He dropped out of college his sophomore year to become an intern at Uptown Records in 1990.

Founded in 1986 by the late Andre Harrell, Uptown Records became the premiere label for hip hop and R&B artists. Based in New York City, Combs worked at Uptown as an A&R executive. It housed talent such as Heavy D, Mary J. Blige, Jodeci, Guy, Lost Boyz and Al B. Sure. Harrell infamously fired Combs in 1993, which led him to start his own label known as Bad Boy Records. “I fired Puff only to make him rich,” Harrell had previously stated.

Bad Boy Records was started in 1993 by Combs. The label’s roster boasted immense talent and included The Notorious B.I.G. (born Christopher Wallace), Faith Evans, 112, Ma$e, The Lox, Total and Carl Thomas. Lil’ Kim was under the mentorship of Wallace and was the only woman in his rap entourage Junior M.A.F.I.A., though she was never technically signed to Bad Boy. Craig Mack’s “Flava in Ya Ear,” released in 1994, was the label’s first hit. However, it was Wallace who would be the epicenter of this era with his debut album Ready to Die eventually being certified 6x platinum.

The most infamous feud in hip hop was between the prominent rap labels of the 90s. Death Row records, founded in 1991 by Dr. Dre, Suge Knight and The D.O.C., housed artists like Tupac Shakur, Snoop Dogg, Nate Dogg and Kurupt. Though Shakur and The Notorious B.I.G. (Christopher Wallace) were once friends, he believed that Wallace was involved the 1994 shooting of Shakur. From there, the two rappers traded jabs on wax; Wallace’s “Who Shot Ya?” was followed with Shakur’s “Hit ‘Em Up.” Shakur was killed in 1996 and Wallace was murdered a year later. Those deaths rattled the hip hop world and inspired Combs to change the direction of his debut album in 1997.

In 1997, Combs released his debut album No Way Out under the moniker Puff Daddy and the Family. It debuted at number one on the Billboard 200 chart. It spurred singles like “It’s All About the Benjamins” featuring The Lox, Lil’ Kim and the late Wallace. “I’ll Be Missing You,” which had cameos by Faith Evans and 112, paid homage to Wallace and became one of the best selling singles of all time. At the 40th Grammy Awards, it was nominated for five awards and won Best Rap album. It is Combs’ most successful record to date.

Launched in 1998 by Combs, Sean John was a clothing line that focused on sportswear for men. Famous musicians, like Pharrell Williams, Nelly, Nas and Usher were featured in ad campaigns for the brand. It garnered Combs the Men’s Designer of the Year award in 2004 by the Council of Fashion Designers of America. Combs sold his majority stake in the brand in 2016 following bankruptcy. However, he bought back Sean John for $7.6 million last year. In a statement to Forbes, he said: “I’m ready to reclaim ownership of the brand, build a team of visionary designers and global partners to write the next chapter of Sean John’s legacy.”

Combs is a proud papa of 6 children. His first biological child, Justin, was born to Combs and designer Misa Hylton-Brim in 1993. With Kimberly Porter (who passed away in 2018) he had adoptive son Quincy (born in 1991), son Christian (born in 1998) and twin daughters D’Lila Star and Jessie James (born in 2006). In 2007, he had daughter Chance with Sarah Chapman. Justin and Quincy famously appeared in an episode of MTV’S My Super Sweet 16, where Combs gifted them cars.

In 1999, Combs and then girlfriend Jennifer Lopez attended Club New York. Later, a shooting took place at the venue and left 3 people wounded. Combs, Bad Boy Records artist Jamal “Shyne” Barrow and Combs’ bodyguard Anthony “Wolf” Jones would be charged in the incident. Combs faced gun possession and bribery charges; he would be acquitted on all counts. Jones was acquitted as well, but Barrow was not so lucky. He was convicted of five charges stemming from the shooting and sentenced to 10 years in prison.

When Making the Band left ABC for MTV, Diddy was at the helm for the newly launched Making the Band 2. It jumpstarted the careers of musical groups like Da Band, Danity Kane and Day 26. Some of the series’ most notable moments include that infamous cheesecake walk to Brooklyn, R&B sing-offs and the legend known as Dylan. Combs would go on to make the VH1 series I Want To Work For Diddy. He also made guest appearances on CSI: Miami.

Ciroc, a French brand of vodka, was founded in 2003. However, it didn’t become popular until Combs was recruited to oversee the liquor’s lifestyle and branding marketing in 2007. “I’m not just a celebrity endorser, I’m a brand builder...I’m a luxury brand builder,” Combs told Billboard shortly after the partnership was announced. He bolstered sales from 50,000 to 2 million cases a year. In 2014, the mogul purchased 50 percent of DeLeon Tequila and launched Ciroc Vodka Spritz last month.

In 2008, Combs received a coveted star on the Hollywood Walk of Fame. He was celebrated as the CEO and founder of Bad Boy Records. Combs’ entrepreneurial endeavors include everything from artist management to music publishing to television and film production. His impact on the entertainment world is indelible as the man himself.

Although Combs would have mainstream success with his stint in reality television, he dabbled with acting in movies as well. He appeared in the 2001 films Monster’s Ball and Made, as well as the 2005 movie Carlito’s Way: Rise to Power. However, it was the film A Raisin in the Sun in which he would receive the most acclaim. It was nominated for an Emmy Award for Outstanding Made For Television Movie. In 2009, he won an NAACP Image Award for Outstanding Actor in a Television Movie.

In 2013, Combs launched cable television network Revolt. It focuses on hip hop culture and produces original content as well as covers breaking news, events and trends in the Black community. It is one of the few Black-owned cable networks and reaches over 55 million homes. Last year, Revolt TV launched its first digital streaming app. Some of its most popular programs include “Drink Champs” and “Revolt Black News.”

In 2014, Combs received an honorary degree in humanities from Howard University. During the ceremony, he received a standing ovation from the crowd as they loudly chanted “Diddy” as he graced the stage. “Howard University didn’t just change my life — it entered my soul, my heart, my being and my spirit,” said Combs said during his speech. “Nobody is going to invite you to the front of the line, you got to push your way to the front of the line.” He also pledged $1 million to his alma mater to establish the Sean Combs Scholarship Fund.

In 2016, Combs and company embarked on the 20-date Bad Boy Family Reunion Tour featuring the most famous talent on their roster: Ma$e, Lil’ Kim, Total, Faith Evans, Carl Thomas, The LOX and 112. The late Black Rob made an appearance as did French Montana, who signed with Bad Boy Entertainment that same year. The most surprising moment of the tour was Shyne’s virtual performance of “Bad Boyz” on a silver screen from Belize.

In 2020, the late Notorious B.I.G. was inducted in the Rock and Roll Hall of Fame. Combs honored him at the virtual ceremony, alongside his two children Tyanna and CJ Wallace. On the Hall of Fame’s website, it said that Wallace called Ready to Die and Life After Death “two of hip-hop’s most influential albums.” During his induction speech, Combs said: “[Wallace] wanted to have influence and impact people in a positive way, and that clearly has been done all over the world.”

Last year, Combs announced the launch R&B label Love Records in collaboration with Motown Records. It also marked his official return to music. In a statement about his latest venture, Combs remarked: “Motown is the perfect partner for my album and I’m excited to add to its legacy.”

In 2022, Combs turned head when he hosted the Billboard Music Awards. “I’m a frequency. I’m the vibe curator. Black Brother Thunder, Chocolate Boy Wonder,” Diddy said during his six-minute monologue. He also urged forgiveness be extended to country star Morgan Wallen for using the N-word and to Travis Scott for being at the epicenter of the Astroworld disaster. “It’s time to forgive. To have Morgan and Travis be able to come back and touch the stage again with the mindset of getting a second chance at life,” he stated.

In December, Diddy shocked the world when he announced on social media that he had welcomed a new child into the Combs family.“I’m so blessed to welcome my baby girl Love Sean Combs to the world,” he tweeted. Diddy was romantically linked to City Girls’ Yung Miami at the time of the announcement. Two weeks after the news, he posted a family photo including Love on Instagram.

In April, Diddy made a surprise appearance at Coachella during Metro Boomin’s headlining set. Alongside The Weeknd, he performed the song “Creepin,’” which samples the 2004 Mario Winans song “I Don’t Wanna Know.” Festival goers were excited by his presence and in awe of the impact he’s had on hip hop over the decades.

In August, during Jackson State University’s first football game of the season against South Carolina State, the Revolt founder presented a $1 million check to the HBCU in Jackson, Miss. In an interview, Diddy said, “If it wasn’t for HBCUs I wouldn’t be here, and really just supporting HBCUs is not just my honor, it’s my responsibility.” He will also continue to invest into the school over the next few years.

On Thursday (August 31), the mogul announced his Love Records debut The Love Album: Off the Grid. Its new single, “Another One of Me,” features The Weeknd and is rumored to be the Canadian singer’s final collaboration under his moniker. The album is scheduled to release on September 15.

In response to the rapid fire filing of sexual assault lawsuits, several businesses responded cutting ties with the music executive. Macy’s pulled his brand of Sean John clothing from all stores and departments. Tsuri, Nuudii System, Fulaba and House of Takura ended affiliations with his e-commerce business, Empower Global. Hulu cancelled plans for a reality show centered on his life. The Recording Academy announced plans to re-evaluate his invitation to the 2024 Grammys after his nomination for Best Progressive R&B album.

Finally, he stepped down as chairman of the music television network he founded, Revolt TV, per The Los Angeles Times.

On March 25, 2024, Combs’ properties in Los Angeles, New York and Miami were raided by the Department of Homeland Security stemming from a search warrant from the Southern District of New York, per ABC 7 News. The purpose investigation is unspecified but it is suspected the raid is connected to the sex trafficking allegations from the several sexual assault lawsuits filed against him. Both of Combs’ sons were detained as agents searched the property. The officers were seen coming out of the mansion with boxes. It’s unclear what was confiscated from the home.

Kalyn Womack Contributed to this article