With his custom-tailored silk clothes, multi-carat diamond jewelry and, according to law enforcement officials, as much as $2 million a week from sales of cocaine and crack cocaine coming in, Rayful Edmond III was the biggest drug dealer in the nation’s capital during the late 1980s.

After he was sent to prison for life, he remained, among some, a legend. In movies, TV and rap lyrics, Edmond was often glorified as a calculating, business-savvy gangster. Even multiplatinum-selling rapper Jay-Z once rhymed on “Can I Live”: “No more Big Willie, my game has grown. Prefer you call me William. Illin for the revenues, Rayful Edmond-like. Channel 7 news, round seven jewels, head dead on the mic.”

But it was largely unknown that Edmond was doing something frowned upon by those in the streets: cooperating with federal prosecutors in the hope that he might someday walk free, also known as snitching in Edmond’s world.

On Wednesday, Edmond will return for the first time in 17 years to his hometown, where authorities say his army of dealers sold $20 crack rocks, contributing to addiction and rising crime that devastated the city.

During at least two days of hearings in federal court in the District, Edmond and his attorney plan to lay out why they believe Edmond’s 20 years of cooperating should result in his life-without-parole sentence being quashed. Edmond, now 54, is expected to take the witness stand to describe how he has spent much of his time behind bars in fear for his life because he has been threatened for helping authorities.

Edmond was sentenced to life without parole in 1990 after being convicted of federal drug distribution in a reign that lasted from 1985 until his arrest in spring 1989. Then this February, federal prosecutors made a startling move, asking a federal judge to reduce Edmond’s punishment in exchange for his help on homicide cases and hundreds of drug cases. They later called for Edmond’s life sentence to be reduced to 40 years.

Edmond’s attorney, Jason Downs, a former D.C. public defender, argues Edmond deserves — and that prosecutors led him to believe the government would seek — a sentence of time served.

No matter what happens to his sentence in the District, Edmond still has to serve a separate 30-year sentence for drug dealing in a Pennsylvania prison. The U.S. attorney in Pennsylvania said no decision had been made on whether prosecutors there would seek a reduction.

U.S. District Judge Emmet G. Sullivan, a District native himself, will make the final decision about Edmond’s D.C. case. Sullivan will consider the years and type of cooperation Edmond provided to prosecutors and the impact of the massive drug ring he ran throughout the city.

Downs declined to comment publicly about his client’s case. But in recent court filings, Downs offered new details about the depth of Edmond’s cooperation. He said Edmond provided information that helped prosecutors obtain wiretap affidavits leading to the convictions of more than 100 people in drug cases.

Edmond testified in two trials and also provided information to D.C. detectives investigating 20 cold-case homicides, Downs wrote. Court papers say Edmond spoke monthly to a prosecutor who was his key contact. Although prosecutors said that information did not result in arrests, they said it allowed detectives to determine which suspects may have had motives and to eliminate other suspects. That cooperation continued through 2014.

Edmond, who was convicted of drug dealing in a Pennsylvania prison after he was sentenced for his crimes in the District, also worked with the Office of the Inspector General to help the Bureau of Prisons overhaul its inmate telephone system and visitation policies to prevent others from selling drugs in prison, Downs said. Edmond’s 30-year sentence in Pennsylvania begins after his D.C. prison term ends.

After Edmond’s first meeting with prosecutors, Downs wrote, “government officials recognized that his cooperation would constitute the intelligence coup of the decade — perhaps of the century.”

But in a filing, Assistant U.S. Attorney John Crabb Jr. wrote that while Edmond’s information was helpful, it was not as vital as Edmond or his attorney argues.

“While the defendant’s cooperation was successful and he is deserving of a sentencing reduction, he engages in hyperbole when he characterizes his cooperation as ‘unprecedented’, ‘unparalleled’ and ‘the intelligence coup of the decade — perhaps of the century,’ ” Crabb wrote.

To aid him in making his decision, Sullivan in May asked the District’s attorney general, Karl A. Racine, to survey residents about Edmond’s proposed early release. About 500 people responded. Half thought Edmond had spent enough time in prison for nonviolent offenses. The other half, some citing the devastating impact of cocaine on the city, said he should serve out his life term.

Edmond was linked to as many as 30 slayings during that period of record-high homicides but was never convicted of any murders.

With Edmond set to testify, security in Sullivan’s courtroom Wednesday is expected to be heightened.

The last time Edmond was in the District was in 2002. At that time, he was a key witness in the trial of his protege Rodney Moore, who was charged with ordering or carrying out 12 killings as part of his own drug operation. Edmond testified behind bulletproof glass. A jury later found Moore and co-defendant Kevin Gray guilty of murder charges. Both were sentenced to multiple life prison sentences.

In May, Edmond appeared in court for a hearing in his resentencing via closed-circuit TV. Wearing a prison jumpsuit and with a receding hairline, Edmond was slightly heavier compared to his lean, basketball-player build before his arrest. His mother, siblings and other family members sat in the courtroom, blowing kisses as Edmond flashed his large smile and blew kisses back.

Edmond is now in a federal witness protection program in an undisclosed facility. If he is released, he would remain in witness protection, Downs has said.

One key witness for Downs could be Assistant U.S. Attorney John P. Dominguez, the prosecutor who Downs says told Edmond — in writing — that he would seek a sentence of time served. Downs contends the U.S. attorney’s office, which has removed Dominguez from Edmond’s case, is reneging on that promise.

Prosecutors deny that Dominguez ever promised that Edmond would be resentenced to time served. In a filing last week, Crabb wrote that during his conversations with Edmond, Dominguez “made it clear that he was expressing his personal views and that he was not empowered to make the ultimate sentencing recommendation.” Crabb went on to add, “Accordingly, contrary to the defendant’s claim, the government’s position regarding sentencing in this matter has never changed.”

Edmond and Dominguez, Downs wrote, started working together on cases in 1994. It was then that Edmond got his first deal from prosecutors. In exchange for his cooperation on other drug cases, Edmond’s mother, Constance “Bootsie” Perry, now 78, who worked in her son’s drug empire, was released nine years into her 14-year prison sentence.

In a three-page memo attached to Crabb’s filing, Dominguez confirmed that Edmond’s cooperation was used to help obtain wiretaps that resulted in 12 federal indictments in drug dealings involving more than 100 defendants.

In his filing, Downs said two witnesses are expected to tell the judge how Edmond, while incarcerated, brokered a truce between two rival gangs in the Simple City neighborhood of Southeast Washington.

Two other people, who Downs said are Edmond’s childhood friends, are expected to testify about how they are prepared to help Edmond transition back to society if he is released.