Sean ‘Diddy’ Combs’ lawyer broke down in tears as she tried to laud his menswear award as a reason he should receive a light sentence. 

The disgraced rap mogul’s attorney Nicole Westmoreland grew emotional as she pleaded with a judge to hand down a lenient sentence on Friday. 

In referencing Mr. Combs winning the Menswear Designer of the Year, it was emphasized that the achievement extended beyond just receiving an award. It marked a groundbreaking moment, as Mr. Combs became the first Black male to secure the accolade in its 23-year history.

Westmoreland was referring to the 2004 Council of Fashion Designers of America prize won by Diddy for his popular Sean Jean clothing line. 

Observers in the courtroom noticed that Westmoreland seemed to become emotional as she spoke, highlighting Combs’ contributions, including the creation of one of the earliest Black-owned music record labels.

‘It wasn’t just about an award, it was about breaking barriers,’ she said. 

‘Mr. Combs is simply a man with imperfections, much like everyone else. He has made mistakes, but how many of us can say we’ve positively impacted numerous lives? He has been incarcerated and is regretful. I communicate with him daily.’

Her remarks followed a stern critique from prosecutors who accused Combs of having excessive pride for scheduling a speaking engagement in Miami.

Combs, now 55, could face a sentence of up to 20 years for prostitution-related charges. However, on Friday, prosecutor Mary Slavik suggested he seemed overly confident.

‘(Diddy) booked speaking arrangements in Miami for next week,’ Slavik told the hushed Manhattan Federal Courthouse.

‘This is the peak of arrogance,’ she noted, arguing that it suggested he anticipated the court would overlook the law, allowing him to be in Miami as planned.

‘That’s the opposite of demonstrating respect for the law… his respect for the law is just lip service.’

Sean ‘ Diddy ‘ Combs’ lawyer broke down in tears as she tried to laud his menswear award as a reason he should receive a light sentence

Diddy’s attorney cited his 2004 award for menswear designer of the year from the Council of Fashion Designers of America (pictured) as a reason he should be freed

Diddy, seen in a court sketch, sat by on Friday morning as his lawyer broke down in tears while she tried to laud his menswear award as a reason he should receive a light sentence

Slavik did not give details of the speaking engagement, but it has since emerged that Diddy booked himself a teaching position in Miami next week to give guidance to prisoners about entrepreneurship.

Court documents seen by the Daily Mail show the mogul is scheduled to deliver his first class to 75 to 100 incarcerated people to teach business, life skills and mentorship, and would follow the same program that he had been giving while behind bars.

Although Diddy would have wanted to frame the engagement as a way to give back, prosecutors took a dim view of the move and said it was an arrogant presumption that he would be free. 

The arguments marked a bad start to the sentencing hearing for the star, with Judge Arun Subramanian also saying he’ll still consider evidence from the crimes Diddy was cleared off when deciding how long to imprison him for. 

Diddy’s trial captured national attention earlier this year as the jury heard weeks of gut-wrenching testimony from his ex-girlfriend Cassie Ventura (seen together), where she alleged that she was coerced into marathon ‘freak off’ sexual performances during their relationship

That declaration saw the anxious-looking rapper bow his head, with one of Diddy’s lawyers also visibly perturbed by the news.

Prosecutors have recommended Diddy spend 11 years behind bars.

His defense says 14 months is sufficient. Diddy has been held in custody in Brooklyn’s Metropolitan Detention Center since September 2024, with a 14 month sentence meaning he’d be a free man by 2026.

Judge Subramanian can use his discretion to decide how long Diddy should be sentenced for and can go longer or shorter than what has been recommended.

Diddy was convicted of two federal prostitution offenses but cleared of far more serious racketeering charges.

That means any unexpected additions to his final sentence could be lengthy ones.

Hours before the sentencing, Diddy’s attorneys released a bizarre promo video presenting himself as a saintly do-gooder on the morning of his sentencing.

The disgraced rap mogul shared a clip through his attorneys on Friday morning, showing the 55-year-old with his children during their childhoods and portraying him as a loving father

The clip appears to have been released in hopes of softening Diddy’s image ahead of his sentencing on Friday morning

The 11-minute clip showed the 55-year-old with his children during their childhoods and portraying him as a loving father, seen playing with his young daughters in archival footage interspersed with Diddy meeting fans and recording music.

The clip appears to have been released in hopes of softening Diddy’s image ahead of his sentencing on Friday morning, showing him growing up from the streets of New York to celebrating lifetime achievement awards and living a life of luxury.

Much of the promotional documentary also focuses on Diddy’s charter school in Harlem, where he is seen speaking with young students alongside montages of them dancing and learning in class.

Diddy faces a maximum of 20 years behind bars for transportation to engage in prostitution of his ex-girlfriend Cassie Ventura and another unnamed woman.

Judge Subramanian previously denied a request from Diddy’s attorneys to release him on a $1 million bond after he was convicted in July.

On the eve of his sentencing on Friday, Combs was hit with fresh sexual assault allegations from two additional alleged victims – a man and a woman – in civil suits. 

Long lines seen gathering at court in New York on Friday ahead of Diddy’s sentencing

Diddy has languished in the Metropolitan Detention Center in Brooklyn ever since he was arrested in September 2024, where he has been locked up with accused CEO shooter Luigi Mangione and convicted crypto fraudster Sam Bankman-Fried.

The disgraced rap mogul’s trial captured national attention earlier this year as the jury heard weeks of gut-wrenching testimony from Ventura, where she alleged that she was coerced into marathon ‘freak off’ sexual performances during their relationship.

In her testimony, Ventura – who was heavily pregnant as she took the stand – claimed that Combs often beat and abused her during their 11-year relationship.

During cross-examination Diddy’s defense attorneys argued that the sessions were not evidence of sex trafficking and were consensual, and brought up text messages from their relationship where Ventura wrote that she ‘loved’ the freak offs.