Charles Vanness admits he was a small player in the District’s crack epidemic of the 1990s, a street-level dealer when the drug’s violent grip helped propel the city to infamy as the “murder capital.”

His third and final conviction for selling came in 1995 after he was caught with an amount of crack equal to the weight of just 22 pennies. It earned him the type of uncompromising mandatory sentence not uncommon for the era: life without parole.

Vanness had no future, but he spent the past two decades preparing like he did. He earned his GED diploma, spearheaded a mentoring program for new inmates and took dozens of trade classes. At 48, he says, he is a different man.

Vanness and thousands of other offenders like him are at the center of a national debate that largely boils down to a single question: Do they deserve a second chance?

The Obama administration announced this year that it will allow nonviolent drug offenders to apply for clemency as part of a larger bipartisan push in recent years to soften the stiff mandatory drug punishments enacted in the ’80s and ’90s. Thousands of inmates have submitted applications, and the Department of Justice has begun sifting through the cases to see which inmates may qualify.

Reform advocates, some judges and many politicians on both sides of the aisle say sentences like Vanness’s are overly harsh, have torn families apart and have consigned them to poverty. They also say that the sentences have been particularly devastating on minority communities.

Some conservative lawmakers and law enforcement groups argue that those long sentences helped reduce violence on the nation’s streets and that releasing drug offenders could lead to more crime, since some statistics show high recidivism among the group.

Vanness, whom an attorney identified as a prime candidate for clemency, could be a test case in the debate.

“I made a big mistake,” Vanness said in a visiting room at a federal prison recently. “What hurts me is that I see people like rapists, child molesters and people that have killed doing less time than me.”

‘No big boy’

Vanness was “no big boy” crack dealer, as he puts it. He said he was raised by a solid family, but he dropped out of Wilson High School in the ’80s and began hanging out on the streets in his Northeast neighborhood.

He said he was drawn to the lifestyle of older drug dealers and began selling. He said he made enough money from dealing to buy basics for his children, make payments on a used car and buy sneakers. He said he never got rich.

By the end of his teens, he had two small-time convictions for dealing.

“I thought I was a player,” said Vanness, who now has a beard marbled with gray. “I was just a street-level dealer trying to impress some girls.”

Vanness’s descent into drug dealing mirrored crack’s rise in D.C. and other cities. By 1991, drug violence helped push the number of homicides in Washington to a record 491 — more than four times the total in 2013.

Congress responded by enacting long mandatory minimum sentences for crack distribution.

In 1994, informants told police that Vanness was dealing out of a basement apartment, according to court records.

Undercover agents approached the apartment to make a controlled buy but saw Vanness driving away.

Police stopped the car, and a passenger told authorities Vanness threw packets of cocaine out a window, court records show. Investigators searched his apartment, turning up 51 grams of crack, cash and a pistol. Vanness was arrested.

In an interview, Vanness claimed that the drugs and gun in the apartment were a roommate’s. Nevertheless, a jury convicted Vanness of possessing with intent to distribute and dealing near a school, since his home was adjacent to Gallaudet University. The jury could not reach a verdict on gun charges, and they were dropped.

When it came time for sentencing, the prosecutor sought an increased punishment based on Vanness’s prior convictions. That triggered a mandatory sentence that left him with a life term.

Vanness vividly recalls that moment in U.S. District Court on June 26, 1995.

“It was like someone hit me with a bat,” Vanness said.

‘A program’

A 2012 report by the ACLU found that there were roughly 3,300 inmates nationwide serving life without parole for nonviolent offenses, and nearly 80 percent were drug offenders. Tens of thousands of other nonviolent drug offenders are serving lengthy sentences triggered by mandatory minimums.

Mary Petras, a federal public defender and Vanness’s attorney, said recent moves to relax penalties for crack distribution “mean the most [Vanness] would get if he was convicted today would be 10 years.”

The daze Vanness felt on sentencing day lasted for a year, he said. He recalls older inmates telling him to get his GED, but he wondered: “GED for what? I got life without parole.”

His depression broke only after his family visited the year after he was incarcerated. He said “something just clicked” after seeing how old his parents looked. Vanness said he had to keep moving forward for them.

He said he decided to focus on finding a way out of prison — after all, laws might change — and improving himself. He called it “a program.”

Vanness began taking GED classes and studying law in the prison library to find a way to challenge his sentence. He had a purpose, but prison still exacted a toll.

“It destroyed my family mentally. It destroyed me mentally,” Vanness said. “I’m just holding on. That’s my story.”

Crystal Jones, Vanness’s eldest daughter, recalls all the times her father wasn’t there. There were illnesses. There was the time a man broke into the family’s home and robbed them at gunpoint. There were the holidays.

“We had such a connection,” Jones said of Vanness, who went to prison when she was 12. “His daughter needs him.”

Then, there were the missed family milestones. Vanness was not there for the birth of his youngest daughter, his grandson or the deaths of his parents.

Vanness recalled his final conversation with his mother, who never gave up hope he would be released: “I don’t know if I’m going to be with you when get out. Go find a wife and be with your daughter.”

Mary Price, general counsel for Families Against Mandatory Minimums, said Vanness’s story is common.

“Mandatory minimums are the crudest of tools,” she said. “They prevent judges from making individualized assessments and force them to impose one-size-fits-all punishments.”

FAMM contends that the mandatory minimums have helped push the federal prison population from 25,000 in 1980 to nearly 218,000 today. The group and others also argue there is a racial disparity in the mandatory minimums.

Those factors have driven a loosening of sentencing guidelines, as well as the Obama administration clemency initiative. But not everyone is on board.

The National Association of Assistant U.S. Attorneys said in a letter to the U.S. Sentencing Commission that the clemency proposal represented a “grave danger.” NAAUSA pointed to a Bureau of Justice Statistics report that showed that between 2005 and 2010, 77 percent of drug offenders were arrested again within five years of their release.

To qualify for clemency, inmates must, among other things, be low-level, nonviolent offenders, have served at least 10 years and demonstrated good conduct in prison.

Vanness said he will apply.

If he is granted clemency, he plans to speak to high school students about the dangers of drugs. And he would reunite with his children.

For the first time in a long time, he can see a future for himself.

“They gave me time like I had trafficked 50 pounds of cocaine. It took me getting life in prison to realize it wasn’t worth it,” Vanness said. “I think I would be a good, productive member of society.”