Diddy Desperately Confronts His Lawyer About 'Losing' In Never-Before-Seen Footage

Sean "Diddy" Combs was left anxious and scrambling for solutions in the moments leading up to his arrest in September 2024.

In a newly released video clip, the embattled rapper is seen angrily confronting his lawyer as he laments "losing" his case. Since then, he has undergone a two-month criminal trial after which he was found guilty of two counts of prostitution related offenses and sentenced to 50 months behind bars.

Sean "Diddy" Combs plans to appeal his sentencing but is reportedly still hoping for a presidential pardon in early 2026.

Diddy battled crippling anxiety as he faced pressure from all quarters in the moments leading up to his arrest in September 2024.

A chilling first look at the upcoming Netflix documentary, "Sean Combs: The Reckoning," offered never-before-seen clips where the Bad Boy Records founder is seen angrily confronting his lawyer, lamenting how they're "losing."

The brief trailer for the documentary was released on Monday, showing Diddy in a New York City hotel room 6 days before he was arrested by Homeland Security officials.

"We have to find somebody that'll work with us that has dealt in the dirtiest of dirty business," he said in what seemed to be a phone call with his lawyer.

He had on a black athleisure outfit in the footage and tried to calm his unsettled nerves by pacing and bouncing his knee up and down.

"We're losing!" he angrily added.

The documentary, produced by rapper Curtis "50 Cent" Jackson and directed by Alex Stapleton, is set to premiere on December 2, 2025, and promises to go deep into decades-long allegations of sexual misconduct, oppression, and abuse of power that have now plagued Diddy.

A short teaser dropped last month, promising "explosive, never-before-seen materials, including exclusive interviews with those formerly in Combs' orbit."

In the trailer released Monday, it was announced that jurors would be interviewed, as well as Aubrey O'Day, and Diddy's Bad Boy Entertainment co-founder Kirk Burrowes, to name a few.

A week after the scenes captured in the trailer, the "I'm Coming Home" rapper was arrested in Manhattan and was subsequently transferred to the notorious Metropolitan Detention Center in Brooklyn, where he stayed for a year.

Meanwhile, the documentary is already gaining global attention, mostly due to 50 Cent's involvement in the project.

The "Candy Shop" rapper mercilessly trolled Diddy on social media during his trial, due to what appears to be a falling out between the music moguls.

Back in 2006, 50 Cent released a diss track that features gunshot sounds and allegations about Diddy's knowledge of Christopher "The Notorious B.I.G." Wallace's killer. He has also claimed that he believes Diddy is linked to the murder of Tupac Shakur, per CNN.

However, Diddy has since denied the allegations, calling them "nonsense" in a 2016 interview on "The Breakfast Club."

Since the new teaser hit the internet, fans have been having a field day, with many talking about how 50 Cent has seemingly taken trolling to a whole new dimension with the Diddyy documentary.

"50 producing Diddy's documentary is the level of petty excellence I aspire to," a fan wrote on X.

Another said, "Diddy having nightmares every time he realises the world is about to see this, from the perspective of 50."

A third fan commented, "Bro, 50 Cent producing a Diddy doc feels like the ultimate flex crossover episode," while someone else added, "Only 50 Cent would beef so hard he turned it into a Netflix original."

"50 Cent's level of pettiness needs to be studied," another user said, adding a crying emoji.

Diddy has since faced trials on charges bordering on sex trafficking, racketeering, and transportation to engage in prostitution. However, he was acquitted on the first two serious crimes and found guilty on 2 counts of the last.

Judge Arun Subramanian then sentenced him to 50 months in jail and ordered him to pay a $500,000 fine.

He was initially staying at the MDC jail in Brooklyn even after his conviction, but later requested that he be moved to FCI Fort Dix in New Jersey to be able to attend its resident drug addiction program and receive visitation from loved ones.

He was expected to have concluded his sentencing by May 8, 2028, but his release date was extended to June 4, 2028. Although the reason why remains unknown, Diddy got into trouble when a prison official caught him drinking homemade alcohol and involved himself in a 3-way call from jail.

He's expected to appeal his sentencing amid talks of an unlikely pardon by President Donald Trump, who distanced himself from the rapper because of his bashful comments about him in the past.