Sean “Diddy” Combs had been planning ahead for his time out of jail before being sentenced to prison.

Despite facing a conviction on two counts of transportation to engage in prostitution, Combs had reportedly scheduled seven speaking engagements for as soon as next week.

The prosecution called this move the “height of hubris,” according to the New York Times.

These speaking engagements, which were set to focus on entrepreneurship, mentorship, life skills, and personal development, were scheduled to take place primarily in the Miami area, where Combs lived before his arrest.

However, his lawyer later clarified that Combs would fill his time with teaching engagements, not speaking engagements, if released.

Combs, 55, was sentenced to 50 months (four years and two months) in prison for his conviction. He had faced a maximum possible sentence of 20 years behind bars.

The prosecution had sought an 11-year prison sentence, citing Combs’ “decades of abuse” and “unchecked violence.” In contrast, Combs’ defense team had recommended a 14-month sentence, considering his time already served since September 2024.

In a surprising move, Combs’ defense team had also contacted the Trump administration earlier this year after President Trump reportedly considered pardoning him. However, this effort ultimately did not come to fruition.

During the sentencing hearing, Combs tearfully apologised to his former girlfriends, friends, and family, calling his behaviour “disgusting, shameful, and sick.”

He expressed remorse for his actions and acknowledged the harm caused to those around him.