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By Joshua Rhett Miller
Senior Reporter
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Sean 'Diddy' Combs is set to learn his fate Friday – and should be prepared to spend several more years in prison, legal analysts told Newsweek ahead of the sentencing.
A jury convicted Combs, 55, of two counts of transportation to engage in prostitution in July following his eight-week trial in New York. But the hip-hop mogul was cleared of sex trafficking and racketeering conspiracy charges that included a potential life sentence.
Each prostitution-related count carries a maximum penalty of 10 years, and prosecutors are seeking a sentence of no less than 135 months — or 11 years and 3 months. Combs’ defense team insist 14 months is a more adequate punishment, which would translate to his near-immediate release from a federal detention center in Brooklyn for time served.
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Ronald Chapman II, a defense attorney who has closely followed Combs’ legal saga, believes Judge Arun Subramanian will “score this case much lower” than federal prosecutors.

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"Federal sentencing begins with an analysis of the sentencing guidelines conducted by the probation department," Chapman told Newsweek Thursday. "The defense and the government have very different views. The difference comes down to whether or not the conduct that Combs was acquitted of should be considered as part of the offense of conviction because it overlaps with the count of conviction."
Subramanian will likely rule the prosecution's request to be an "overreach," Chapman said.
"This is principally because the Supreme Court has recently been very skeptical of sentencing defendants based on acquitted conduct," Chapman said. "I believe the judge will claim to not use acquitted conduct, but still sentence Combs to some prison time."

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Subramanian has previously doled out sentences below probation department recommendations in other cases, “signaling a belief that the guidelines often score too high,” he said.
Chapman expects Subramanian to sentence Combs to up to 80 months in prison, or 6 years and 8 months. Conversely, the hip-hop mogul could receive as little as 70 months, he said.
“But this could swing drastically either way based on how the guidelines fight turns out during the sentencing hearing,” Chapman added.
Seth J. Zuckerman, a criminal defense attorney and former prosecutor in New York, said he expects Combs to receive roughly four to five years in prison, slightly less than the recommendation by federal probation officials of up to seven years and three months.

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Prosecutors on Tuesday submitted letters from key witnesses against Combs, including the singer Casandra Ventura Fine, his former girlfriend of roughly 11 years, to Subramanian ahead of Friday's sentencing.
“If there is one thing I have learned from this experience, it is that victims and survivors will never be safe,” Ventura Fine wrote. “Although I can hope for justice and accountability, I have come to not trust anything. I hope that your decision considers the truths at hand that the jury failed to see.”
Ventura Fine said she still has “nightmares and flashbacks” on a recurring basis following her tumultuous relationship with Combs. The 39-year-old singer previously told jurors she felt coerced to partake in drug-fueled sex sessions with Combs and escorts he hired, testimony that formed the basis of the government’s claim that the music mogul orchestrated a sprawling criminal enterprise to fulfill his sexual desires.
“For over a decade, Sean Combs made me feel powerless and unimportant, but my experience was real, horrific, and deserves to be considered,” Venture Fine’s letter continued. “While the jury did not seem to understand or believe that I engaged in freak offs because of the force and coercion the defendant used against me, I know that is the truth, and his sentence should reflect the reality of the evidence and my lived experience as a victim.”

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Subramanian rejected a request Tuesday by Combs’ attorneys for his conviction to be overturned entirely, dismissing claims that Combs had acted as an amateur pornographer who wasn’t engaging in prostitution and that the verdict violated his First Amendment rights.
“That argument fails for two reasons,” the judge wrote. “First, Combs’s conduct is not protected by the First Amendment … And the same goes for the desire to view a pornographic performance — at some point, illegal activity can’t be laundered into constitutionally protected activity just by the desire to watch it.”
Two former federal prosecutors, Mark Chutkow and Jen Beidel, said they expect Combs to be sentenced to four to seven years, aligning with the recommendation by federal probation officials.
Combs, who has been held without bail for nearly 13 months, is set to be sentenced at 10 a.m. Friday in federal court in Manhattan. Subramanian granted a request last week by defense attorney Teny Geragos to allow him to wear “non-prison clothing” during the proceeding. He’s also expected to address the judge prior to learning his fate.
At least four members of Combs’ defense team plan to partake in the hearing, which will also include a 15-minute video, court documents show.
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