One became a cop. The other a crook.
Copeland chased drug dealers. Winestock was a drug kingpin.
And it would be three decades before they met again and learned they shared a determination to pass along the lessons life had taught them to teenagers already in the court system and wrestling with their decisions.
Winestock concedes that the message he is delivering, to find a job or career, isn't one he would have heeded in the 1980s. It wasn't one he was ready to hear, he said, when he was raking in thousands of dollars supplying corner dealers at about a dozen spots citywide.
"It would have been hard for me to listen, I am not going to lie. It was like a high," said Winestock, now 52.
Two long prison terms helped start his transformation.
Inside, he watched younger inmates brawl over issues as trivial as which rappers earned the most money and was incredulous so minor a point could set off a fight. Thirteen years into his sentence, Winestock's focus on reaching troubled youth sharpened after he learned that his father, then 69, had been shot dead by a young man who had been like a son to him.
For Copeland, who spent 28 years as a D.C. officer until his retirement two years ago, mentoring was a natural extension of a street-level ministry he began even before he left the force. That calling, said Copeland, also 52, compels him to try to reach wayward teens in a community that often distrusts law enforcement.
The pair ran into each other three years ago at a charity backpack giveaway.
That began a renewed connection and a new camaraderie.
"They are more alike than different. They operate from the heart more than the head," said the Rev. Donald Isaac, who recruited both to work for most of 2017 in Credible Messengers, a city-funded mentor program for teens who are under the supervision of the Department of Youth Rehabilitation Services (DYRS) for car thefts, drug trafficking, armed robbery and other violent offenses.
The pair recall similar childhood days in the city, with Copeland raised by his grandmother in Anacostia and Winestock in his parents' single family neighborhood of Woodridge in Northeast Washington.
"I always liked nice things. I used to love to dress," Winestock recalled.
His mother was a Howard University pharmacologist, but it was his father's fascination that left its mark.
He was a devoted gambler, Winestock said, and his love of racehorses, running numbers and shooting dice in the streets seeded a love of quick money in his son.
Winestock's first job doing housekeeping at Howard University Hospital offered a steady paycheck but couldn't finance the Jordache and Calvin Klein designer jeans that turned girls' heads. Cash pulled in at $5 and $10 craps games after middle school and selling $10 bags of marijuana could.
His parents insisted on good grades as a condition of playing basketball and football with Boys Club No. 12 and later with Spingarn High School.
Dice games and basketball introduced him to people in pockets across the city, and on those pillars, Winestock started building his drug operation.
He moved up from paper bags of weed to supplying large quantities of cocaine, PCP and, eventually, heroin. His first car had been a used Chrysler. Within three years, he was driving an Audi 5000 to his 1984 graduation.
"That's when it started getting serious for me. It was amazing the respect you could get by selling drugs," Winestock said. At commencement, "I walked across the stage with a big rope chain and a Scarface medallion. Everything was gold."
Copeland loved clothes and girls, too, but followed his grandmother's advice to always work for his bread.
Copeland scraped together money as a retail cashier and stocker at a drugstore and later in a Church's Chicken kitchen.
After high school, he attended Norfolk State University for two years but ran out of money and dropped out. His police training started in 1988 for a simple reason: He needed a job, and D.C. police were hiring.
"Back in 1988, we called D.C. Dodge City," Copeland said. "A lot of moms and dads and youth were on crack cocaine. Folks on PCP and angel dust, a lot of people dying from heroin."
He worked on patrol and later in high-powered jump-out squads that swarmed corners to seize guns, drugs and money.
But Copeland never encountered the big and flashy Winestock, who, by the time Copeland hit the streets, had already owned a Mercedes-Benz E-Class, a Maserati and a Jaguar and lived in a luxury apartment.
Winestock's dice games upgraded to playing at Atlantic City and Las Vegas casinos.
He partied with the elite, including University of Maryland basketball star Len Bias, whom Winestock considered a friend.
Bias's death from an overdose 48 hours after he was chosen by the Boston Celtics as the second overall pick in the 1986 National Basketball Association draft brought federal investigators to an associate of Winestock's who laid out the extended drug operation.
By December 1990, Winestock had been arrested and indicted as the head of the loose-knit organization known as the Woodridge Group after a two-year federal investigation.
In 1992, Winestock was convicted of drug distribution charges and on Oct. 5, 1993, was sentenced to two life terms without the possibility of parole.
The sentences shook him deeply, but soon after arriving at Leavenworth federal prison in Kansas, Winestock started to prepare physically and mentally as if he would one day come home.
He earned the nickname "Law Library" because he studied so much and began mentoring younger inmates after prison officials allowed him to start and take part in counseling programs.
A change in federal sentencing rules and 23 years of good behavior enabled his release in 2013, and Winestock returned to live in the same neighborhood he had plagued — but with a promise to himself to honor his father's memory by doing what he could to prevent more young people from starting on a path that could lead to killings.
He got a business license and started an industrial cleaning company using a 1992 Ford van. He created a nonprofit organization called Saving Our Next Generation to connect youngsters to counseling and people reentering the community from prison to vocational training.
In front of teens, Winestock is blunt and practical. Copeland is warmer and emotional.
Winestock explains how he was a first-time offender who got two life terms.
"I made a major mistake at 24 years old. But right now, they have way more opportunities than we had," he said. "They need to take advantage."
Forget what rappers make, he has said in sessions for the Credible Messengers program, and plot your own financial path: How do you plan to finish high school? Do you know how to train for a job, apply for one, keep it? How will you build a credit history?
He urges them to have what he didn't: patience in setting the right course.
Copeland aims to cut through the street swagger and bravado of young men and women who have already made at least one major mistake and let them know that someone carries hope for them.
"We told you that we love you and there's nothing you can do about it," Copeland told teens in a DYRS group in Anacostia last year.
When he confronts the teens, it is about how they respond to situations and how they can improve. Do people take kindness for weakness? If you have a family, how have your actions affected their lives?
Sometimes his questions were met with the glazed eyes of bored teenagers. Others paid attention but needed to be drawn out to fully share feelings about forgiveness, love, family and integrity.
Guiding a teen to finish school, find a job or enlist — like one who recently joined the Navy — marks success. Helping replace a cellphone or offering rides when they're needed are shows of support and help build trust.
A teen mentored last summer in Credible Messengers had narrowly avoided a 15-year sentence for a string of armed robberies because he was arrested at 14 and sentenced as a juvenile.
He spent about two years in DYRS custody, where he managed to graduate from high school early. The Washington Post generally does not identify teens charged as juvenile offenders.
"In here, they are really talking about how it really is," the teen said in an interview, explaining that he learned through the program how his choices have an effect on his mother and his future.
Winestock remains with Credible Messengers. Copeland left the program in October to focus on a teen crime prevention program for local students with Code 3, a nonprofit organization founded by former officers to strengthen police-community relations. He also works with his "I Am My Brother's and Sister's Keeper" ministry.
Their work together continues this month, Winestock said, as they plan a winter coat and toy drive to honor the Jan. 25 birthday of Winestock's father.
"We support one another. If he can't make it, I get the rebound," Copeland said. "We are teammates."
Correction: A previous version of this story stated that Len Bias was top overall pick in the 1986 National Basketball Association draft. He was the second.