For over two decades, Sean “Diddy” Combs has been recognized as a versatile figure in hip-hop, successfully transforming his musical talents into an expansive business empire. This included launching a record label and a clothing brand, running a TV network, securing deals with liquor brands, and playing prominent roles in reality television. However, recent revelations have surfaced, portraying a darker side to Combs’ story.
U.S. prosecutors have accused Combs of preying on and abusing women behind closed doors, with allegations claiming a network of associates helped him in silencing victims through blackmail and violent means. Combs has entered a not guilty plea, firmly rejecting these accusations. His trial commenced with testimony beginning on Monday.
Here are some pivotal moments from Combs’ rise in the industry and the subsequent controversies that followed:
**1990 — 1999**
In 1990, Combs, a Howard University student, gained entry into the music industry through an internship at New York’s Uptown Records. By December 28, 1991, a tragic incident at a celebrity basketball game he promoted resulted in nine casualties. As thousands attempted to enter a gym at City College of New York, a report attributed some of the blame to Combs for inadequate event planning.
By 1993, after leaving Uptown Records, Combs founded his own label, Bad Boy, which later struck a profitable deal with Arista Records. In 1994, Bad Boy released Notorious B.I.G.’s “Ready to Die,” amid ongoing tensions in the music scene, including allegations related to the shooting of Tupac Shakur. Tragically, in 1997, Notorious B.I.G. was shot and killed. In his memory, Combs, going by Puff Daddy, released the tribute song “I’ll be Missing You.”
Throughout 1998, Combs’ career hit new heights as he garnered two Grammy awards. His entrepreneurial spirit also led to founding the Sean John fashion line. However, 1999 marked a tumultuous year for Combs, who faced legal challenges following a nightclub shooting and was later arrested on gun charges.
**2001 — 2008**
Combs was acquitted of charges related to the nightclub incident in March 2001, although his protégé, Jamal “Shyne” Barrows, was convicted and served time. Combs announced his stage name change to P. Diddy shortly after. His career then ventured into television, producing and starring in “Making the Band.” By February 2004, he performed live at the Super Bowl halftime, further stretching his influence in entertainment.
Combs also extended his talents to theater, concluding with a Broadway debut in “A Raisin in the Sun” in 2004. He altered his stage name again in 2005, dropping P to simply “Diddy.” His accolades included receiving a star on the Hollywood Walk of Fame in 2008, marking an illustrious period in his career.
**2015 — 2022**
In 2015, Combs faced charges linked to an altercation at UCLA, though the charges were later dismissed. He focused on education, launching a Harlem charter school in 2016 and contributing $1 million to Howard University. By 2017, Forbes named him the highest-earning celebrity at that time, bringing in $130 million within a year.
The following year, Kim Porter, a significant figure in Combs’ personal life, tragically passed away. Yet in 2022, he was celebrated with a lifetime achievement award at the BET Awards.
**2023 — 2025**
Combs returned to music in 2023 with “The Love Album — Off the Grid.” That November, he faced legal issues when R&B singer Cassie accused him of prolonged abuse, including rape. Although the lawsuit was quickly settled, a spate of additional allegations emerged from multiple women and men.
Disturbing developments continued into 2024 when federal agents searched Combs’ residences. By May, footage surfaced showing Combs assaulting Cassie, leading him to publicly apologize. In September, he was arrested in Manhattan following allegations of sex trafficking and racketeering, using his conglomerate as a coercive tool in various abuses.
The case entered its trial phase by May 2025, ushering in what promises to be a closely-watched and consequential moment in Combs’ life and career.