Byron Lamont McDade, who is serving 27 years on drug charges, in the family visiting room at the federal corrections facility in Loretto, Penn. (Michel du Cille/The Washington Post)

The judge regretted it from the beginning. The 27-year prison sentence he gave Byron Lamont McDade was too long, he said, for a low-level player in an expansive cocaine enterprise. Years later, the punishment still nagged at him.

In two decades on the federal bench in the District, Paul L. Friedman has passed judgment on hundreds of people who committed crimes: murder, kidnapping, fraud.

The 324-month term — mandated by federal sentencing guidelines — was the longest the judge had imposed for a drug offense. More time than he gave a gang leader in a murder case. Three times as much as he gave any of McDade’s more culpable comrades in the drug conspiracy.

Twelve years later, Friedman might finally be in a position to do something about McDade’s sentence.

“The court has not lost hope, and presumably Mr. McDade has not either,” Friedman wrote in an opinion this spring. The judge used his ruling on a procedural issue in the case to identify McDade as a “prime candidate for executive clemency.”

Paul L. Friedman, U.S. district judge for the District of Columbia, poses for a portrait in his courtroom on July 28 in Washington. Friedman presided over McDade's trial on drug offenses. (Michel du Cille/The Washington Post)

McDade, who grew up two blocks from the Frederick Douglass Home in Southeast Washington, is one of tens of thousands of federal inmates who may benefit from a sweeping bipartisan movement away from historically harsh drug penalties in the U.S. criminal justice system.

This year, the Obama administration announced that it would seek early release for thousands of nonviolent drug offenders who already have served years in prison. Since then, nearly 4,000 inmates have submitted applications to the Department of Justice seeking reduced sentences, and more than 20,000 have returned initial surveys seeking free legal representation to determine if they are potential candidates.

The Justice Department will recommend eligible inmates for clemency, and President Obama will make the final decision. So far, no inmates’ sentences have been reduced.

The effort is one of the signature initiatives of Attorney General Eric H. Holder Jr., who announced last week that he is stepping down. It is also among a series of steps taken in recent years to address inequities in drug-related sentences, including retroactively reducing punishments, in some cases.

Many judges have long agonized over their limited discretion in sentencing, but only a small group has tried to do something about it.

The clemency initiative is open to candidates who meet six criteria:
1. inmates who are currently serving a federal sentence in prison and likely would have received a substantially lower sentence if convicted of the same offense today;
2. are non-violent, low-level offenders without significant ties to large-scale criminal organizations, gangs, or cartels;
3. have served at least 10 years of their sentence;
4. do not have a significant criminal history;
5. have demonstrated good conduct in prison; and
6. have no history of violence prior to or during their current term of imprisonment.

“Every one of us has had cases where you absolutely had no choice but to sentence someone to a term that you experienced as unjust,” said Nancy Gertner, a former federal judge in Massachusetts who now teaches at Harvard Law School.

But even with a federal judge in your corner, she said, there are no guarantees for inmates like McDade.

Friedman and others, she said, are “reduced to begging these other authorities to do the right thing.”

No serious criminal record

McDade has his own regrets. He knows he should not have run when federal agents came looking for him in March 2000.

At the time of his arrest, McDade was a 32-year-old married father of four with two jobs and no serious criminal record. He had a misdemeanor gun conviction, for which he had been ordered to pay a $10 fine.

He was accused of taking part in what was then one of the largest drug conspiracies in the Washington area — involving more than 750 kilograms of cocaine from a Florida-based supplier.

One of the ringleaders of the drug operation was a social friend of McDade’s from weekend bowling matches and trips to the carwash on Martin Luther King Jr. Avenue SE. Phyllis Webster drove a red BMW, shot pool for money and wore her bangs swooped across one eye. She also owned the Midtown Cafe, a restaurant and club on Georgia Avenue in Northwest.

McDade, whom friends call “Barry,” and his wife vacationed in South Beach with Webster one weekend.

McDade knew that Webster had money, and there was talk of her trouble with cocaine in the 1980s. What he did not know was that Webster’s phone calls were being monitored by the FBI.

Webster and three others were arrested, and they quickly cut plea deals with prosecutors.

McDade still says that he wasn’t involved in drug dealing, that he never saw any cocaine. But when the FBI initially tried to arrest him, he fled, leaving the trash truck he was driving behind a motel on Route 7 in Tysons Corner. McDade was on the run for seven months before he turned himself in.

At trial, Webster testified against McDade, fingering him as her lieutenant who kept the bookkeeping records on the back of lottery tickets.

“I trusted Barry,” she testified during McDade’s four-week trial in February 2002.

In one recorded conversation described for the jury, Webster called McDade and said she needed information from his “lucky Lotto numbers sheet.”

Later that day, Webster told McDade on the phone, “You are the center of the puzzle.” The jury believed her.

McDade knows now that running made him look guilty, and he accepts the jury’s verdict.

“It was the dumbest thing I ever did. I didn’t know how to deal with the situation,” McDade said during an interview in the visiting room at a federal prison in Western Pennsylvania about 40 miles from Johnstown. “That’s probably what hurt me the most.”

Byron Lamont McDade is serving 27 years on drug charges at a federal corrections facility in western Pennsylvania. (Michel du Cille/The Washington Post)

Webster and McDade’s other co-defendants were out of prison in less than eight years. He has stayed inside while the world, and his family, has changed.

When McDade’s mother, Jeannette, died of lung cancer in January, he watched a recording of her funeral from the prison chapel. McDade had too many years left on his sentence, he said, to submit a viable application for a supervised trip to the service at Glenarden Baptist Church.

He has never met the five nieces and nephews born during his absence. He has never watched his youngest child, who is headed to college to play football, on the field.

“My life revolved around them,” he said of his children. “But I’ve been gone 14 years. I really don’t know who they are anymore.” The youngest, who was 3 when McDade went to prison, “doesn’t really know who I am.”

As a child, McDade and three siblings slept together on the pullout couch, living “like sardines” in a two-bedroom apartment, one of his attorneys said. Despite his family’s limited means, McDade had a promising start.

He liked working with his hands. After graduating from Anacostia High School in 1986, he held a series of jobs as a plumbing apprentice, a UPS loader and a car detailer. He started a company to take elderly and disabled people to medical appointments and picked up a second job driving a trash truck in Northern Virginia.

Now 46 and scheduled to be released in 2024, McDade’s dark hair is turning gray. He has a thin mustache, black-rimmed glasses and a simple gold wedding band. Before he was transferred to a lower-security facility this fall, McDade walked four miles a day on the rural prison grounds that were once a Catholic seminary. He was learning Spanish from the Latino inmates he worked with in the prison’s digital cable factory.

In late April, McDade was sitting in the chow hall when a friend from the cellblock told him about the judge’s opinion naming him as a good candidate for early release. McDade was elated.

“This might be my year,” he said in a phone call to his wife and in e-mails to friends.

“There are a lot of other guys like me. They are sitting around praying and hoping that they get released,” McDade said. “We’ll wait and see what happens.”

New early release rules

From his sixth-floor court chambers with a view of the U.S. Capitol, Friedman is waiting, too.

At McDade’s sentencing hearing in May 2002, Friedman said he deserved significant jail time for participating in the far-reaching cocaine operation but that the mandatory guidelines’ sentence was too long. At 324 months, the judge put McDade at the lowest possible end of the guideline range, a calculation that factored in the amount of drugs involved and McDade’s role as a manager.

“I wish I could do more, Mr. McDade,” Friedman said at the time.

Years later, in 2009, when the judge considered an unrelated legal filing from McDade, he was reminded of the far shorter sentences he had given McDade’s co-defendants.

By then, the Supreme Court had ruled in U.S. v. Booker that judges were no longer required to stick to sentencing guidelines, which Friedman said in a recent interview had become like “straitjackets.”

Paul L. Friedman, U.S. district judge for the District of Columbia, poses for a portrait in his courtroom. (Michel du Cille/The Washington Post)

Byron Lamont McDade poses for a portrait in the visiting room in the corrections facility in Loretto, Penn. (Michel du Cille/The Washington Post)

At the time, Friedman wrote that if he’d had that latitude when McDade was sentenced, he would have given him a substantially shorter prison term.

Then, for the first and only time — out of nearly 500 sentences Friedman has handed down — the judge recommended that the Bureau of Prisons seek a reduction in McDade’s sentence. Friedman also urged Obama to consider commuting his term. The judge got no response from either office to his unusual request.

Obama, like his recent predecessors, has been slow to use his powers to commute prison sentences.

This spring, as Friedman was reviewing a renewed legal request from McDade, the Justice Department formally announced its criteria for identifying inmates eligible for early release. They must be nonviolent offenders who have served at least 10 years and shown good behavior in prison.

The judge again put McDade forward, this time urging his attorneys to petition for clemency “so that justice may be done in this case.”

“The sentence this court was required to impose on Mr. McDade was unjust at the time and ‘out of line’ with and disproportionate to those that would be imposed under similar facts today,” Friedman wrote.

“While the court is powerless to reduce the sentence it was required by then-existing law to impose, the president is not.”

McDade’s attorneys, Mary E. Davis and Christopher M. Davis, said they will soon present his case for clemency to the Office of the Pardon Attorney.

Justin Jouvenal and Alice Crites contributed to this report.