During a debriefing session with federal investigators, James Rosemond, the music manager-turned-cocaine kingpin, was reportedly questioned about the sexual preferences of entertainers, including whether Sean “Diddy” Combs was “having sexual relationships with under age boys,” according to a U.S. District Court filing.

In an affidavit included as part of a new trial motion filed last month, Rosemond recounted his involvement in a series of nine pre-trial “proffer” sessions in late-2011. The meetings were attended by Rosemond, his lawyers, federal prosecutors, and Drug Enforcement Administration and Internal Revenue Service agents.

The purpose of the meetings was to allow federal investigators to question Rosemond, 48, about his criminal activities and evaluate whether he should be offered a cooperation agreement in advance of his narcotics trafficking trial. Facing overwhelming evidence of his guilt, Rosemond’s best chance of avoiding life in prison was to strike a deal with Department of Justice lawyers.

However, investigators eventually declined to cut a deal with Rosemond, who was subsequently convicted at trial of running a drug ring that sold millions of dollars’s worth of cocaine. Rosemond, who is nicknamed “Jimmy Henchman,” faces a mandatory term of life in prison when sentenced October 25 in Brooklyn federal court.

In advance of Rosemond’s first proffer session, defense lawyers provided investigators with the names of eight of his cocaine suppliers, according to court filings. During the proffers that followed, Rosemond implicated himself in a pair of homicide plots, described his drug distribution network, and copped to other crimes.

Rosemond was also quizzed during an October 4 session about his contacts with several public figures, including Combs, Rev. Al Sharpton, and musician Wyclef Jean.

At Rosemond’s trial last year, IRS Agent Marc Van Driessche testified that, during the proffer session, investigators questioned the music industry figure about his business transactions with Sharpton and Jean, and asked whether either celebrity engaged in illegal activity. Rosemond denied any improprieties on the part of Sharpton or Jean.

Van Driessche recalled that Rosemond was also asked about Combs since, “We had information through other witnesses that the defendant may have made an admission to Sean Combs.” The nature of this purported admission was not the subject of further testimony. Van Driessche added that Rosemond described having business dealings years earlier with Combs, and that they had a “cordial relationship.”

In his September 6 affidavit, Rosemond (seen at left) contended that he reluctantly agreed to the proffer sessions arranged by Gerald Shargel, his former lawyer. Rosemond added that investigators sought to get him to confess to crimes for which he had no involvement. “When the defendant said he didn’t know about a certain event…they accused him of lying,” Rosemond claimed.

The confrontational sessions turned “awkward,” Rosemond stated, when an investigator showed him “naked pictures” of different women. The purpose of this purported investigative technique is not revealed in Rosemond’s affidavit.

A prosecutor, Rosemond continued, then “asked about entertainers sexual preferences, including, but not only, Sean Combs having sexual relationships with under age boys.” Again, Rosemond provided no context for these alleged queries.

During Rosemond’s trial, Shargel complained to Judge John Gleeson that federal prosecutors and agents were only seeking “trophies” when they questioned Rosemond about celebrities during the proffer sessions. And, when Rosemond provided nothing of substance on the high-profile figures, “disappointed” investigators rejected his client’s bid for a cooperation deal. Prosecutors countered Shargel’s claim, declaring that Rosemond was untrustworthy and lied during the debriefing sessions.

Some of Rosemond’s admissions during the proffer sessions were used against him during his criminal trial. In the new trial motion, Rosemond’s current attorney argues that Shargel provided “ineffective assistance of counsel” by improperly “opening the door” to the government’s use of the damaging proffer material.

Federal investigators are barred from discussing the details of confidential proffer sessions, the notes from which are not public. Shargel, Rosemond’s ex-attorney, declined an interview request about the debriefing sessions.