Maybe he should have listened to his fated protege Biggie Smalls - Mo Money, Mo Problems.
Heralded for decades as rap royalty, Sean Diddy Combs now sits alone in an isolation cell in a notorious New York City jail - deemed too much of a threat to the community by authorities to be let out even after offering a $50 million bond.
Its a stunning fall for the Its All About the Benjamins rapper, who was once hip-hops wealthiest and most influential mogul.
But if the feds allegations are true it may be just be all the unlimited cash, unchecked power and the Hollywood privilege that goes along with it that landed Diddy where he now sits: facing a slew of racketeering conspiracy and sex trafficking charges that accuse him of presiding over a sordid empire of sexual crimes and physical abuse.
If convicted the 54-year-old could spend the rest of his life behind bars.
So how did we get here? Here is a look at the key events that have unfolded since prosecutors announced he was being investigated late last year.
November 16, 2023
Cassie says in a lawsuit that Combs subjected her to years of abuse, including beatings and rape.
Cassie, whose legal name is Cassandra Ventura, signed to Combs label in 2005, and the two were on-again-off-again romantic partners for more than a decade starting in 2007.
The lawsuit filed in federal court says Combs was prone to uncontrollable rage and subjected her to savage beatings.
It says he plied her with drugs, forced her to have sex with other men, and raped her in her home as she was trying to end the relationship in 2018.
Combs, through his attorney, vehemently denies the accusations.
November 17, 2023
With staggering speed, Venturas lawsuit is settled the day after it is filed.
The terms of the agreement are kept confidential.
We have decided to resolve this matter amicably, Combs says in a statement. I wish Cassie and her family all the best. Love.
Cassie Ventura (L) and Sean Combs attend the China: Through The Looking Glass Costume Institute Benefit Gala at the Metropolitan Museum of Art on May 4, 2015 in New York City
Cassie, whose legal name is Cassandra Ventura, signed to Combs label in 2005, and the two were on-again-off-again romantic partners for more than a decade starting in 2007
November 23, 2023
Two more women accuse Combs of sexual abuse in lawsuits filed on the eve of the expiration of the Adult Survivors Act, a New York law permitting victims of sexual abuse a one-year window to file civil action regardless of the statute of limitations.
The lawsuits, filed by Joi Dickerson and another woman who was not named, allege acts of sexual assault, beatings and forced drugging in the early 1990s by Combs, then a talent director, party promoter and rising figure in New York Citys hip-hop community.
Combs attorneys call the allegations false.
November 28, 2023
Combs temporarily steps down as chairman of his cable television network, Revolt, because of the wave of sexual abuse allegations.
It would be one of several business setbacks for Combs brought on by the lawsuits.
December 6, 2023
A woman alleges in another lawsuit that in 2003 when she was 17, Combs and two other men raped her.
The lawsuit filed in federal court in Manhattan says she was living in a Detroit suburb and was flown to a New York studio, where she was given drugs and alcohol that made her incapable of consenting to sex, and the men took turns raping her.
The same day, Combs posts a statement on Instagram broadly denying all the allegations in the mounting series of lawsuits.
I did not do any of the awful things being alleged, the post says.
I will fight for my name, my family and for the truth.
Sean P Diddy Combs, Justin Bieber and Sean Kingston perform at the Help for Haiti benefit concert and telethon at AmericanAirlines Arena on February 5, 2010 in Miami, Florida
Sean Diddy Combs is one of Americas most famous rappers, record producer and record executives
February 26, 2024
A music producer files a lawsuit alleging Combs sexually assaulted him and forced him to have sex with prostitutes.
The lawsuit gives a long list of potentially illegal activities dealing with drugs and sex that the producer says he witnessed.
A lawyer for Combs calls the allegations pure fiction.
March 25, 2024
Homeland Security Investigations serves search warrants in early morning raids on Combs homes in Los Angeles and Miami in what officials declare is a sex-trafficking investigation.
Combs was at one of his homes in Miami at the time. His two sons, at his home in Los Angeles, were handcuffed during the search, Combs attorneys said.
Officials did not say whether the raids were prompted by the civil lawsuits, but Combs attorneys said they believed they were.
March 26, 2024
Combs lawyer calls the raids a gross use of military-level force and says Combs is innocent and will continue to fight to clear his name.
The attorney, Aaron Dyer, says there is no excuse for the excessive show of force and hostility exhibited by authorities or the way his children and employees were treated.
Properties connected to rapper Sean Diddy Combs were raided in March by federal agents
A picture from inside Diddys Miami home shows how law enforcement agents conducted thorough searches
These aerial images taken in October 19, 2023, show the sprawling waterfront properties owned by the embattled rap mogul, real name Sean Combs, that were raided by federal agents
Homeland Security Investigations serves search warrants in early morning raids on Combs homes in Los Angeles and Miami
April 4, 2024
A lawsuit that names Combs as a co-defendant alleges that his son Christian King Combs sexually assaulted a woman working on a yacht chartered by his father.
The lawsuit filed in Los Angeles Superior Court says Sean Combs created the circumstances that led to the assault and paid to cover it up afterward.
An attorney for the two men calls the allegations outrageous.
April 26, 2024
In the first major piece of legal pushback from Combs and his team, they file a motion to dismiss several elements of Dickersons lawsuit because they were not illegal in 1991 when the alleged incidents occurred.
While the legal objections are procedural, the filing also slams the numerous false, offensive, and salacious accusations in the lawsuit.
May 10, 2024
Combs asks a federal judge to dismiss the Dec. 6 lawsuit that alleged he and two co-defendants raped a 17-year-old girl from Michigan in a New York recording studio.
Again, the objections are procedural - alleging the lawsuit was filed too late under the law - but the court document calls its claims false and hideous.
May 17, 2024
CNN airs video that shows Combs attacking Ventura in a hotel hallway in 2016.
The video closely mirrors an assault described in her lawsuit, which said Combs had already punched her that night, and she was trying to leave the InterContinental Hotel in Los Angeles when he woke and came after her.
In the footage, a man who appears to be Diddy, wearing only a towel, punches Ventura, kicks her, and throws her on to the floor.
The lawsuit alleges Combs paid $50,000 to take away the video at the time. Combs representatives had no immediate comment.
The Los Angeles District Attorneys Office says it cannot prosecute Combs for the attack shown in the video due to statute of limitation, noting that no case had been presented to prosecutors.
CNN in May aired a leaked video that shows Combs attacking Ventura in a hotel hallway in 2016
This frame grab taken from hotel security camera video and aired by CNN shows Sean Diddy Combs attacking singer Cassie in a Los Angeles hotel hallway in March 2016
Diddy, wearing only a towel, punches Ventura, kicks her, and throws her on to the floor
May 19, 2024
Combs posts a video on Instagram and Facebook apologizing for the assault on Ventura.
Its his first real acknowledgement of wrongdoing since the recent stream of allegations began.
My behavior on that video is inexcusable, Combs says, adding that he had hit rock bottom.
I take full responsibility for my actions in that video. I was disgusted then when I did it. Im disgusted now.
I went and I sought out professional help. I got into going to therapy, going to rehab. I had to ask God for his mercy and grace. Im so sorry.
June 10, 2024
At the request of New York Mayor Eric Adams, Combs returns a key to the city.
Adams sent letters to Combs rescinding the honor as part of the fallout of the leak of the video of Combs beating Cassie.
Adams says he was deeply disturbed by the video. Adams awarded Combs with the key at a ceremony in 2023.
A day earlier, Howard University announced it had rescinded an honorary degree given to Combs and disbanded a scholarship program in his name.
On May 19, Combs posted a video on Instagram and Facebook apologizing for the assault on Ventura. That was his first real acknowledgement of wrongdoing since the recent stream of allegations began
At the request of New York Mayor Eric Adams, Combs in June returned a key to the city
August 26, 2024
As part of a multi-faceted pushback against the lawsuits filed against him, Combs asks a federal judge to throw out the February lawsuit from the music producer.
His lawyers say the suit was overrun with tall tales, lurid theatrics, legally meaningless allegations and blatant falsehoods whose intent is only to generate media hype and exploit it to extract a settlement.
September 11, 2024
Diddy is sued by singer Dawn Richard in a case describing years of psychological and physical abuse, including groping, that she says she suffered as he helped launch her career.
Richard, a member of the girl group Danity Kane and is well-known for appearing on the MTV reality show Making the Band, alleges in the suit that she witnessed Combs abuse Cassie and was afraid of the mogul.
Diddys representatives accuse Richard of making an attempt to rewrite history by manufacturing a series of false claims all in the hopes of trying to get a pay day - conveniently timed to coincide with her album release and press tour.
Combs poses for a selfie between a pair of fans ahead of his arrest on September 16
Authorities had planned on arresting Combs on Tuesday, but something happened that caused federal officials to take him into custody earlier than planned, an official told the outlet
September 16, 2024
Combs is arrested on a Monday night in New York after a grand jury indictment. No details on the charges were made public, but federal officials say they will ask a judge to unseal the indictment a day later.
Combs attorney calls it an unjust prosecution of an imperfect person who is not a criminal.
The rapper, clad in a long black coat over a black t-shirt with gray sweatpants and grey sneakers, was seen hours earlier flashing smiles and posing for selfies with several adoring fans as he wandered the streets of midtown Manhattan.
Christian, Combs 26-year-old son who performs under the moniker King Combs, was also seen walking with his father before his arrest.
Earlier in the day, a video shared on social media showed Diddy flicking through his phone and enjoying the sunshine as he sat in Central Park, wearing a baggy black vest.
September 17, 2024
Combs was denied bail as he appeared in a Manhattan federal courtroom on shocking sex trafficking and racketeering charges that revealed a debauched lifestyle and serious allegations of sexual and physical abuse.
U.S. Attorney Damian Williams, in revealing what federal agents found during the March raid of Diddys Miami residence, displayed graphics that showed off confiscated unmarked AR-15s, ammunition, as well as 1,000 bottles of baby oil and other lubricant.
The indictment alleges that between at least 2008 and the present, Combs abused, threatened and coerced victims to fulfill his sexual desires, protect his reputation, and conceal his conduct, Williams said.
The indictment alleges that Combs used and exploited women and other people for years, and in a variety of ways. As alleged, Combs used force, threats of force, and coercion to cause victims to engage in extended sexual performances with male commercial sex workers, some of whom transported, or caused to be transported, over state lines.
They also revealed evidence had been gathered of Combs’ long-rumored sex parties — which he referred to as freak offs — during their raids on his Los Angeles and Miami homes, finding, electronic devices that contain images and videos of the freak offs, with multiple victims.
Diddy liked to plan and control the sex performances, the feds alleged, that sometimes lasted days at a time, and involved sex workers and a variety of narcotics such as ketamine, ecstasy, and GHB, which Combs distributed to the victims to keep them obedient and compliant.”
Diddys legal team offered a $50 million package to secure his release from jail, including the rap moguls Miami mansion, worth $48 million, as collateral.
It also includes the home of Diddys mother, valued at $2 million.
September 24, 2024
Combs is sued by a woman who claims the rapper raped her and recorded the assault.
The alleged victim, Thalia Graves, says the music mogul, 54, and his head of security Joseph Sherman raped her the Bad Boy Records studios in New York back in 2001.
The alleged victim, Thalia Graves, says the music mogul, 54, and his head of security Joseph Sherman raped her the Bad Boy Records studios in New York back in 2001
Graves claims she was 25 and dating one of the rappers employees when she was lured into a meeting by Diddy, who said he wanted to discuss her boyfriend’s supposed performance issues.
According to her lawsuit, Diddy and Sherman sequestered her and gave her a drink that was likely laced with a drug that eventually caused her briefly to lose consciousness.
In the lawsuit, obtained by DailyMail.com, Richard claims that she was manipulated by Combs on promises that he would help her music career.
She also alleged that during the audition process for Making The Band, Sean had called female contestants various names, such as fat, ugly, b****es and also h***.
In response, Erica Wolff, an attorney for Sean Diddy Combs, told DailyMail.com: Mr. Combs is shocked and disappointed by this lawsuit. In an attempt to rewrite history, Dawn Richard has now manufactured a series of false claims all in the hopes of trying to get a pay day — conveniently timed to coincide with her album release and press tour.