On Oct. 8, Combs's lawyers asked an appellate judge to approve the "Last Night" rapper's pretrial release "on appropriate bail conditions." That includes a $50 million bail agreement that prohibits him from witness tampering, the prospect of which was part of the reason why he was denied bail twice by two different judges. Combs's attorneys call the district court's ruling "purely speculative" and argue that the "sensationalism surrounding his arrest has distorted the bail analysis."

In a separate legal filing obtained by Yahoo Entertainment on Wednesday, Combs's attorneys say their client wishes "to assert his right to a speedy trial" as they seek a spring start date. Here's the latest in the case as legal experts break down what his third appeal request means.

Trial date requested

The defense and prosecution wrote a joint letter to Judge Arun Subramanian, who is expected to preside over Combs's criminal trial, outlining issues they intend to address at an Oct. 10 hearing. This is different from the bail appeal filed on Tuesday, which will be heard by a separate court.

Combs's attorneys requested an April or May 2025 trial date. The government simply wrote that it "will be available for trial on a date set by the court, although it remains within the court's discretion to set a trial date at the outset of the case or at a later time."

Whether Combs will be behind bars or under house arrest in his Miami mansion awaiting trial remains to be seen.

Why the appellate court is different — and why it could matter

Criminal defense lawyer Mark Reichel tells Yahoo Entertainment "there are two issues at play that are different" in terms of Combs's bail appeal.

"First, the appellate judges have far fewer cases and will have much more time to study and consider the issues. It is a much more sterile environment for an analysis of the law and the facts," he explains. The Sacramento, Calif.-based attorney says appellate courts lack "the drama and passion of the trial court" as there are no witnesses in the courtroom and "the defendant is usually not there."

However, Reichel says there is one notable "downside," which is the "standard of review."

"The appellate courts are not there to simply rehear every argument from the lower court. They are only there where you can show there was a substantial error. They allow the lower courts wide discretion in the rulings," he says.

Combs's motion 'makes a compelling point'

Reichel thinks it's "a close call" as to whether Combs should be released, highlighting the defense's "compelling" bail proposal.

The $50 million bond is secured by Combs's home in Miami Beach. He agreed to home detention with GPS monitoring. Private security officers would monitor the Bad Boy Records founder at all times and limit visitors to an approved list, including no female visitors other than family members or mothers of his kids. His passport would be surrendered, and he's trying to sell his private plane. Combs's attorneys repeatedly pointed out that he had the means and opportunity to flee after Homeland Security raided his homes but didn't.

"[Combs] has done everything he can do to mitigate any potential tampering with witnesses and possible flight. He has made it impossible for the prosecutors to argue that he could flee. His offer makes that a physical impossibility," Reichel says.

Celebrity lawyer Chris Melcher is surprised Combs was not granted bail with the above conditions.

"Despite the seriousness of the charges, it is surprising that Diddy is being held in custody because he has no criminal record, he voluntarily went to New York to surrender himself, he offered a $50 million bond, and was willing to subject himself to electronic monitoring," Melcher, who is based in the L.A. area, tells Yahoo.

"In his appeal, Diddy argues that there's no credible evidence that he attempted to influence a witness. The prosecutor will need to present solid evidence of witness tampering or take the risk that he could be released," Melcher adds.

Is the 3rd time the charm for Combs?

Experts agree it seems unlikely Combs will be freed after two judges already denied his request.

"It is not common for defense lawyers to file multiple bail motions trying to get their client out. The courts demand there be a change of circumstances in order to bring another bail motion meaning — a change that was not apparent or known when the original bail motion was denied," L.A. criminal defense lawyer Silva Megerditchian tells Yahoo, adding that she believes it was a misstep for Combs's defense team to call out "media sensationalism."

"It is noteworthy that the lawyers seem to mock the lower judge, stating that sensationalism and the media frenzy essentially distorted the bail argument and ruling," she continues. "I do not believe this will be a successful argument to any higher judge reviewing the motion."

Reichel says that despite Combs's compelling bail package, he thinks the appellate court "will simply affirm" prior rulings.

Looking ahead

It appears that "voluminous" discoveries will be addressed at Thursday's hearing given the defense and prosecution's joint letter.

The government has already turned over search warrants in the case, iCloud reports for two of Combs's accounts and his phone that was seized in the March raids, "which defense counsel specifically requested be produced in the first production."