As of this writing, Sean “Diddy” Combs is still serving out his four-year (50 month) sentence at FCI Fort Dix in New Jersey. That sentencing came down in late 2025 months after Combs was convicted on two counts of transportation to engage in prostitution. 56-year-old Diddy is set to be released from prison in June 2028 and, in the meantime, many are weighing in on what might lie ahead for him after his stint behind bars. Aubrey O’Day, who worked with Combs in the early aughts, is now sharing a concern she has about his eventual release.
In the 2000s, singer Aubrey O’Day appeared as a contestant on Diddy’s Making the Band 3, which ended with her being selected as a member of the girl group Danity Kane. O’Day was fired from the band by Combs in 2008 alongside bandmate D. Woods. As of late, O’Day has been reflecting on her interactions with Diddy amid his continued legal issues. The “Automatic” singer was recently sat down with Variety and was asked about what lies ahead for her ex-mentor after prison, and she opined that he would remain unchanged:
I am unsure that the amount of time that he’s going to be in prison is enough to fully, solely do the type of work that you would need to become a better person and to — how do I say this? To heal into the type of person that could be effective and good going back into life, and I’m mostly worried that a lot of money and a great spin team could create the idea that he has once again recreated a new version of himself. And that worries me, because there are people that will always be around to be able to potentially be pulled into that.
Sean Combs’ flood of legal issues began in earnest in late 2023 when his former girlfriend, Cassie Ventura, filed suit against him for alleged violence, sex-trafficking and more. That suit was settled by Combs’ legal team in less than 24 hours but, in the months that followed, others would sue Combs on the grounds of similar claims. The “Victory” rapper was arrested in 2024 and went on trial between May and July 2025. As part of the case, Ventura and more testified against him.
Aubrey O’Day was not called to take the stand and eventually stated that she was glad she didn’t have to appear in court. However, O’Day did open up during Sean Combs: The Reckoning, a four-part docuseries that’s streamable with a Netflix subscription. During the third episode, O’Day accused Combs of sending her sexually explicit emails in 2008 and said she was fired from Danity Kane due to not giving into his advances. In the doc, O’Day also read an affidavit, which detailed a man’s account of allegedly seeing her get sexually assaulted by Diddy and another male.
Before Diddy’s sentencing hearing last fall, O’Day shared additional comments. O’Day opined that during the hearing, the Sean John mogul’s legal team would attempt to rehabilitate his image and stress that he’d “repent” from his ways. Ultimately, during the session, Diddy apologized to those he’d wronged. Before the sentence came down, Cassie also expressed concern over her former partner receiving a light sentence, as she believed he’d seek “retribution” towards her and others.
As Cassie, Aubrey O’Day and others express concern about Sean Combs’ post-prison life, he and his legal team are currently seeking to get him released earlier. Combs’ legal team is working to appeal his sentencing, and the process seems to be moving forward. Shortly after his prison transfer in November, Combs landed a legal win when a judge ruled that the appeal process could be expedited. In the event that the necessary paperwork is filed and the process goes accordingly, the lawyers could present oral arguments in April.
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