Sean ‘Diddy’ Combs arranged to speak in Miami on Monday, presumably thinking he’d remain free, according to recent statements made during his sentencing hearing.

The 55-year-old rapper, facing a possible 20-year sentence for prostitution charges, appeared optimistic, said prosecutor Mary Slavik on Friday morning.

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

‘It’s incredibly presumptuous,’ she remarked, citing this action as evidence that Combs assumed the court would disregard legal consequences and allow him to attend the event in Miami.

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

It has since emerged that Diddy booked himself a teaching position in Miami next week to give guidance to prisoners about entrepreneurship. 

Court documents reviewed by the Daily Mail reveal Combs is set to address a group of 75 to 100 incarcerated individuals, offering lessons in business, life skills, and mentorship, continuing the work he began while incarcerated.

Although Combs likely intended to present this engagement as a charitable act, prosecutors criticized it, viewing it as a presumptive belief that he would avoid imprisonment.

Diddy’s sentencing hearing has gotten off to a bad start for the star. Judge Arun Subramanian has said he’ll still consider evidence from the crimes Diddy was cleared off when deciding how long to imprison him for.

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 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.

Prosecutors have asked the judge to sentence Diddy to just over 11 years, while his defense requested no more than 14 months with time served, meaning he would be freed by the end of the year.

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.

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.