The Untold Truth Of Diddy
Trigger warning: The following article contains mentions of violence and sexual assault.
Sean "Diddy" Combs' rap empire grew famous in the late 1990s with the rise of music legends like the Notorious B.I.G. and Mary J. Blige. Artists under his representation shot to fame, earning Diddy the reputation of a force to be reckoned with in the industry. While his Bad Boy Entertainment company became one of the most successful record companies in the rap game, he had a lot more to manage outside of the studio. Sean Combs had a rap sheet of his own — and not the lyrical kind. While he racked up millions of dollars in profits producing his hit tracks and those of other artists, he dodged scandal after violent scandal on the streets.
Diddy shot to fame during a period where shootouts were how rival rap stars handled beef. The "Last Night" artist has a history of being entangled in violent crimes, one that managed to fly beneath the radar due to his immense success and profit-churning empire. The Harlem native is a hustler by nature, raised by a single mother who supported his ambitions to make it big. While Diddy climbed the ladder to become one of the richest music moguls in the industry, there's a lot that the public may not know about the rapper. He's an entrepreneur with several businesses outside of the music industry, but he could lose everything if found guilty of a sex trafficking probe that saw federal agents raiding his house in March 2024. We're breaking down the untold truth of Diddy.
Diddy's father was killed when he was just a child
Sean Combs' childhood was marked by tragedy. The Sean John founder was raised by his mother Janice in the New York City neighborhood of Harlem after his father was fatally shot when Diddy was just 3 years old. Combs' father Melvin was a drug dealer at the time, a path Diddy said his father was driven to due to a lack of opportunities. "During his time, that was the way out of Harlem—either that or playing basketball," he told O, The Oprah Magazine (via CheatSheet) in 2006.
A derailed transaction led to Melvin's death in 1972 when he was shot in his vehicle after being incorrectly identified as an informant. Janice attempted to shield her son from the circumstances surrounding his father's untimely death, but the rapper ended up piecing the puzzle together on his own. "My mother always told me that he died in a car accident," he said in a 2014 commencement speech at Howard University (via XXL). "But something about that it just didn't feel right." Diddy later discovered the truth after learning of his dad's past from fellow Harlemites and researching old newspapers to learn how he really died.
Diddy's first job was a paper route
Long before Diddy became a household name, he was working as a paper boy in Virginia. After spending much of his childhood in Harlem, he and his mother moved to Mount Vernon, where he attended a prestigious Catholic school and found a way to make money of his own at just 12 years old. "My mother had five jobs. I'm from the roots of hustle," he told the Mirror, adding, "I was a paperboy, the first entrepreneurial thing I did." A young Diddy hustled enough to earn $1000 a week on his routes by offering to take his colleague's routes for half the money in addition to his own route.
Sean Combs may hold a nearly billion-dollar fortune today, but, like many other celebrities, held a job while still in high school. The entrepreneur's day-to-day looked a lot different as a teenager. "I was a busboy in a restaurant, I pumped gas at a gas station, I also had to keep the bathrooms clean," he revealed. "They are the worst but I was proud to make them clean and see people's faces when they came out."
While going from cleaning toilets to managing a nearly billion-dollar empire is quite the come-up, Diddy's maternal influences taught him at a young age the value of hard work and success. "My mother played the role of a father, and my grandmother played the role of my mother," he told Oprah Winfrey (via CheatSheet).
He's a college drop out
Diddy knows a thing or two about business — something he studied for a short time when he attended Howard University. The music mogul majored in business studies at the college for two years before dropping out to pursue a music career in 1990.
Despite not receiving his diploma, the rapper admits he looks back on his time at the school with fond memories. He returned to his old stomping grounds in 2014 to receive his honorary doctorate in humanities from the university, as well as to deliver that year's commencement address. "Howard University didn't just change my life – it entered my soul, my heart, my being and my spirit," he shared with the crowd (per Billboard). "Nobody is going to invite you to the front of the line, you got to push your way to the front of the line."
The "I'll Be Missing You" artist has since given back by donating millions of dollars over the years to Howard University. Not only has he supported their business school, but the producer has also offered internships to Howard alumni at Combs Global.
He started his career in music as an intern
Sean Combs knows a thing or two about hustling to make his dreams a reality. The Bad Boy Entertainment executive got his start in the music industry at an early age, interning at Uptown Records while he was still at college after rapper Heavy D arranged for him to meet label executive Andre Harrell.
Balancing his business studies and his extracurricular pursuits, Diddy would frequently skip classes (with the permission of his professors) for his internship. Eventually, he dropped out of Howard to focus on his music career full-time, and he was eventually promoted to vice president of talent and marketing divisions at the label.
Combs helped produce music for Father MC, Christopher Williams, and Mary K. Blige while at the label, but ultimately his entrepreneurial spirit caused strife within the company. At the time, Diddy was trying to get his own company, Bad Boy Entertainment, off the ground. He tried to get Uptown Records to distribute his new label, but he was ultimately fired. He was able to work a distribution deal with Arista Records, founding Bad Boy Entertainment in 1993 and even poaching some of Uptown Records' signees.
Diddy kickstarted Notorious B.I.G's career
One of the artists who left Uptown Records for Bad Boy Entertainment was Christopher Wallace, known by his artist name Notorious B.I.G. or Biggie Smalls. Sean Combs had originally signed Wallace to Uptown Records, but the rapper switched labels and kickstarted his career under Diddy's representation. The up-and-coming East Coast rapper, known for his incredible freestyling ability and unmatched flow, turned out to be a huge success for Combs and his label.
Biggie Smalls went on to earn Diddy a pretty penny in his rags-to-riches come-up. Originally from Brooklyn, the rapper reached astonishing heights in his short-lived career, with his first album, "Ready to Die," going quadruple platinum. His career was cut short after he was killed in an infamous drive-by shooting in 1997, and decades later, the murder remains unsolved.
Diddy posthumously released Biggie's double album "Life After Death." The album is considered one of the best rap albums of all time and reached Diamond status in just three years. The music mogul also released his own critically acclaimed track, "I'll Be Missing You," in honor of Wallace's death, which featured the rapper's widow Faith Evans. While Wallace's time as an artist ended too soon, his career marked one of Diddy's biggest success stories. Years later, Diddy is still committed to his legacy. "I think I'll always feel some sort of responsibility because I'm in this thing with him. He's my artist," Diddy said on "The Wendy Williams Show."
He was involved in a nightclub shootout with his ex-girlfriend Jennifer Lopez
Sean "Diddy" Combs and Jennifer Lopez were once at the scene of a nightclub shooting that ended with the former couple being charged with possession of a stolen gun. Combs and J.Lo were celebrating Combs' former Bad Boy signee Shyne's upcoming album at a Midtown nightclub at the time, and they were nearly outside the establishment before mayhem ensued. While filing out of the club, Combs accidentally bumped into a clubgoer, knocking his drink over.
The clubgoer was Matthew Allen, who went by his street name "Scar." While it's disputed whether Allen or Combs started throwing wads of cash around, money reportedly started raining down "like confetti," and insults were thrown between Allen and Combs which resulted in guns being drawn. Shots were fired, leaving three people injured, including one woman who was shot in the face and swears it was Diddy who fired the gun.
Lopez and Combs were arrested after the incident, but their charges were eventually dropped, despite witnesses attesting to seeing Comb pull the trigger. Ultimately Shyne was convicted of the shooting and sentenced to 10 years in prison. Natania Reuben has since come out as a victim of the shooting, and she settled a lawsuit against Diddy in 2011 over the ordeal. "I am the woman who he shot in the face in that Dec. 27, 1999, Club New York shooting. I have told everyone, ad nauseam, since then. I watched him fire the gun," she said in a TikTok video in 2024.
Diddy is a mama's boy
Diddy has a special place in his heart for his mother. The Bad Boy Entertainment founder's mother, Janice, took on a huge responsibility when her husband was tragically killed, leaving her as the sole provider for her 3-year-old child. Throughout Sean Combs' childhood, Janice worked multiple jobs in order to move them out of Harlem and to allow her son to chase his dreams. "She almost killed herself to make sure I went to private schools, to expose me to travel," Diddy told Oprah Winfrey in 2006 (via CheatSheet). "She made sure I never looked down on other people. She also ignited a fire in me."
Janice also supported Diddy in the midst of some of his most controversial moments, including the 1999 nightclub shooting in New York. "She wanted me to be bigger than my circumstances," he shared. "During the trial, she walked by me every step of the way." The entrepreneur recalls his mother teaching him some hard-knock lessons in life, including when someone stole his money. "She said, 'Go back out there and get that money — and if anyone ever puts their hands on you, make sure they never do it again,'" he explained. "She knew the reality — if people smell weakness, they take advantage of you."
Diddy gave his mother the ultimate gift on her 80th birthday when he surprised her with a $1 million dollar check and the keys to a brand new Bentley. "That's my hero right there," he said in a video (via 9MagTV), "Ain't nobody like your momma."
He's a successful entrepreneur with multiple businesses
Diddy has launched several businesses and partnerships in his lengthy career, but many of them have dropped like flies in the wake of the damning accusations against him. One of Sean Combs' largest business ventures has been his Sean John clothing brand, which was launched in 1998. The fashion brand has suffered ups and downs throughout the years, with Diddy selling off most of his ownership in the company in 2016. He ultimately saved the company from bankruptcy in 2021, and now holds a majority stake in the company that brings in an annual revenue of nearly $9 million dollars.
The parent company of several of his brands is Combs Global. Other brands include his media company, Revolt, as well as his liquor company, Combs Spirits. Diddy also had a massive stake in the liquor business, partnering with Ciroc vodka to help promote the brand for over a decade and partnering with liquor giant Diageo to buy his DeLeon tequila brand in 2013. Diddy dissolved his relationship with both brands in 2024, however, citing a lack of investment by Diageo.
Several of Diddy's businesses jumped ship following several sexual abuse allegations lodged against him beginning in 2023. As of this writing, more than a dozen companies have severed their business relationships with the mogul's e-commerce site Empower Global, despite Diddy maintaining his innocence. "We believe in victims' rights, and support victims in speaking their truth, even against the most powerful of people," House of Takura founder Annette Njau told Rolling Stone.
Diddy has a reputation for mistreating his artists
Can anyone forget the time Diddy made his Danity Kane girl group walk from Manhattan to Brooklyn just to get him a slice of cheesecake? Many haven't — including many of his former artists who say the man had a reputation for managing them with an iron fist.
Diddy took over MTV's "Making the Band" in 2002, launching several platinum-selling artists like Da Band, Danity Kane, and Day 26. His grueling grooming techniques became a harsh reality for band members, with many of his training sessions ending in tears for several of his artists. Decades later, some of his former musicians are still holding a grudge — and have since spoken out against the music mogul, alleging they suffered mistreatment and poor management at the hands of Diddy. Da Band's Freddy P took to Instagram in 2022 to slam the music executive, claiming Diddy took away his desire to rap. "It's these n***** like Puffy, he my main motherf*****' reason why I really hate f*****' life, dog. People don't even understand," he wrote in a since-removed post (per Vibe).
Danity Kane's Aubrey O'Day and Dawn Richards have also called out the rapper, claiming he was prone to sexist behavior. O'Day, who was fired from the band and told by Diddy that she was overly "promiscuous" told Cosmopolitan, "Puff plays one of the dirtiest games there is around and that's what we were exposed to at 17 years old."
Diddy's ex-girlfriends have accused him of abusive behavior
Diddy's ex-girlfriends have some major beef with the Bad Boy Entertainment head. His ex-girlfriend, Gina Huynh, came out against him in an interview from 2019, saying their five-year relationship was filled with physical abuse. In the interview with Tasha K, the model says she began dating Diddy while he was on a break from his long-time girlfriend Cassie, but he was prone to violence and often compared her to the "Me & U" singer.
In one instance, Huynh recalled the rapper lashing out so hard she was pleading for it to stop. "He stomped on my stomach really hard — like, took the wind out of my breath," she claimed. "I couldn't breathe. He kept hitting me. I was pleading to him, "Can you just stop? I can't breathe." Huynh claimed that Diddy offered her $50,000 dollars to have an abortion, which she refused in order to prove that she truly loved him.
Diddy's ex-girlfriend, Cassie, made similar allegations when she sued her former partner in November 2023. The singer dated the entrepreneur on and off for 10 years, and she claimed she was raped, physically abused, and forced to engage in sex acts with other males in front of him — sometimes once a week. The lawsuit was settled just one day after Cassie filed, with Diddy denying the accusations against him. "We have decided to resolve this matter amicably," the music mogul said in a statement (via Vulture). "I wish Cassie and her family all the best. Love."
If you or anyone you know has been a victim of sexual assault, help is available. Visit the Rape, Abuse & Incest National Network website or contact RAINN's National Helpline at 1-800-656-HOPE (4673).