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Bernie Hammond had been selling heroin since he was 11, but that didn’t mean he didn’t have rules. One rule: Don’t sell drugs to pregnant women. Another: Stay away from arguments on the street. But now, in August 2012, he was about to break one of the guidelines that had kept him out of prison for so many years: He bought a gun.

Hammond’s return tour in the D.C. drug trade was not going well. What had started that April as a way to pay for his lung medication and daughter’s physical therapy degree—with enough left over, hopefully, for his fashion-school tuition—had turned sour. The FBI almost grabbed him at one aborted deal in the District, which had also left potential buyers convinced he was a snitch.

It only cost him $50 and a gram of heroin to trade to a crack addict for the flimsy Saturday Night Special, but Hammond intended to make it count. He spray-painted the 9-millimeter gun tan to confuse would-be attackers for a split second, an idea he got from an old copy of Soldier of Fortune, and hid it in his house on Baltimore’s Brentwood Avenue. And that’s exactly where Baltimore police would find it later that month after catching him on the way to a heroin deal.

Suddenly, Hammond was officially part of the War on Drugs, caught in the ongoing back-and-forth between law enforcement and dealers. In September, Hammond claims, FBI agents offered him two choices: testify against an alleged Washington drug dealer and leave his mother in Anacostia to face whatever consequences came from snitching, or stay silent and fight charges that carried 10 years in prison. Instead, he chose neither: He called a reporter.

Hammond’s sitting next to me in an Adams Morgan Starbucks on Nov. 7, logging into the Gmail account we’ll share. He’s suspicious of both his court-appointed attorneys and the FBI handlers who want him to testify, and he thinks someone’s monitoring his email account. So he created a new account for us to share attachments as draft emails—a circuitous process that nevertheless gets me an FBI-created summary of his September interview with federal agents, which he obtained from his lawyer.

But then, Hammond’s familiar with workarounds—he’s been dealing with them all his life. Now 43, he dropped out of school in seventh grade to start slinging cocaine and pot around his Congress Heights neighborhood. The location was good but too close to his own home; the neighbors could see him selling in Congress Park and tip off his mother. To avoid her scrutiny, he started packing up his drugs each morning and trekking across the Anacostia River to a spot on 9th Street NW.

Still, Hammond didn’t feel removed enough. After three years of dealing, he had saved $2,500—enough to buy an ounce of cocaine from a dealer and leave behind low-level pushing for good. At 14, he became what he still calls himself to this day: a businessman.

Looking at Hammond, it’s easy to see why he’d want to get off the street—and why he was dealing so badly with being pulled into the FBI’s orbit. With his husky build and permanent hangdog face, it’s hard to imagine him lasting long as an enforcer or, less likely still, the kingpin. To make an underground economy career even less viable, he suffers from sarcoidosis, an inflammatory disease that has left him with the lungs of a man twice his age. The disease, which usually starts with shortness of breath, can soon turn into skin lesions and even blindness. Hammond explains it more simply: It’s what comedian Bernie Mac had.

Hammond blames his sarcoidosis on his work in and around insulation as an electrician. In between drug dealing, he picked up the skill as a teenager. He married in his late teens and found himself working both of his trades to support his wife and, eventually, his young daughter. Things turned sour for Hammond around 2001—his wife divorced him, and he was putting more cocaine up his nose than on the street, according to his FBI interview. After he was diagnosed with sarcoidosis when he was 32, a doctor gave him 18 months to live.

Hammond didn’t die, though, and he even stopped dealing for a time after a religious awakening. But in April 2012, he found himself unemployed in Baltimore after another money-making scheme flopped. He was running out of money to pay for his sarcoidosis medication. Hammond’s pride was as much at stake as his health: If he stopped paying for his daughter’s education, his ex-wife would know about his money problems. It was time to return to the only business that had ever reliably paid off for him: drug dealing.

This time, though, he would sell heroin instead of cocaine. Baltimore was steeped in the drug, and heroin that was considered low-quality in Baltimore was still prized in cocaine-heavy D.C. With just an hour-long trip between cities each way, he could flip cheap Baltimore heroin to District dealers who wanted to diversify their merchandise.

At first, Hammond’s return to drug-dealing went well. But he wasn’t making much. One deal for 10 grams, he would later tell the FBI, cost $800. By the time he got the drugs down to Washington, though, he could only sell them for $900—a $100 profit for a sizable risk. He told the FBI he didn’t dilute or “cut” the heroin, reducing its purity while expanding his volume. Still, his Washington customers complained about quality, which suggested that his supplier was tampering with the heroin before Hammond bought it.

Hammond needed to get around the most immediate middle-man, but he didn’t have enough money to pay his supplier for an introduction to someone higher up the distribution chain. He knew who might lend him the money, though: Kenilworth Fats.

In a press release sent out months later, after Fats was arrested by federal agents, the U.S. Attorney’s Office would claim that Fats, 47, ran a drug crew in Northeast Washington’s Kenilworth Gardens public housing complex. Through a friend in North Carolina, Hammond was able to get an interview with Fats in D.C., he would later tell the FBI.

Fats, whose real name is Tony L. Adams, was once a leader in a District drug crew prosecutors called “The Committee.” A 1988 Washington Post story on drug convictions against Fats and other members of the Committee made the front page of the paper. In the story, Fats comes across like white Washington’s fever dream of an ’80s drug boss: chopping up rocks with a razor blade, buying weapons, managing an apartment full of female crack cooks.

(How Fats got his nickname, by the way, is straightforward. As Hammond explained, Kenilworth Fats is fat, and he lives in Kenilworth.)

Decades after his turn in the spotlight, Fats isn’t as fearsome, even if the weight that earned him his nickname is still there. He has high blood pressure, diabetes, high cholesterol, and sleep apnea, according to a request from his lawyer that he receive medical leave from jail. Fats’ condition is so bad, according to his lawyer, that he can’t breathe at night without an air pressure machine.

Hammond himself was amazed that federal agents would ever waste their time with the ailing alleged drug dealer. “I don’t even think Kenilworth Fats is rolling like he used to roll,” he says.

Unfortunately for Hammond, there was a wiretap on Fats’ phone, according to documents filed by prosecutors. With each phone call, Hammond became more entangled in the FBI’s investigation.

Hammond had unwittingly found himself a target of the Safe Streets Task Force, a 20-year-old partnership between the FBI and D.C.’s Metropolitan Police Department. Since its launch in 1992, the partnership had organized a string of busts, from a Congress Heights drug market in 1999 to a violent gang in 2000. And now it was about to get one more.

When Hammond got in touch with Fats, agents had already been surveilling the alleged kingpin for over a year, as part of a larger investigation into the Baltimore-Washington heroin trade. One of Fats’ lieutenants had sold heroin to an undercover officer, while a search of Fats’ basement revealed a backpack filled with cutting supplies, according to an indictment against his crew. Fats has pleaded not guilty to the charges against him. His lawyer didn’t respond to a request for comment on the case.

Wiretaps on Fats’ phone captured all of the mundane responsibilities of running a drug business, according to a motion filed by prosecutors to oppose Fats’ release from jail: going to a GNC fitness supply store to buy powders to cut with the heroin, meeting with suppliers to try out the potency of heroin batches.

In June, according to the FBI, the wiretap on Fats’ phone recorded five conversations between Hammond and Fats. Hammond eventually met Fats and an associate outside the Shrimp Boat on East Capitol Street, according to Hammond’s recollection. Hammond had hoped that his reputation as a no-nonsense “businessman” would convince Fats to lend him the money to buy out his Baltimore supplier. In exchange for the loan, he would sell Fats 25 grams of the heroin at wholesale prices.

The meeting appeared like the kind of mundane drug deal Hammond thrived on: driving to a seafood restaurant, walking from his car to Fats’ truck, getting in, all while Fats’ associate stood guard outside. As he sat in Fats’ car, though, Hammond realized the buyout plan was over before it started. Fats explained that he didn’t have enough to front him the money, Hammond would later tell the FBI. The two forty-something alleged dealers parted without a deal.

Unluckily for Hammond, it wasn’t the last time he would try to make a deal with Kenilworth Fats. On June 29, Hammond paid $1,750 in Baltimore for 25 grams of heroin. He planned to sell them to another Congress Park dealer, but when he got to Washington, he discovered that dealer didn’t have enough money to buy the drugs. After unloading a couple of grams with other dealers, Hammond says, he thought of one man he knew was interested in buying heroin: Fats. The two agreed to meet that day on 60th Street NE, Hammond would later tell the FBI.

Something felt off ahead of the meeting. When Hammond got there, he tossed the heroin in a McDonald’s bag and threw it nearby, waiting for Fats. Suddenly, a group of what looked like white, college-aged men drove by. Hammond, suspicious of what a group of white men would be doing in the neighborhood, called off the trade and walked away from the fast food bag.

Hammond’s quick thinking didn’t earn him credit with Fats, though. Instead, the alleged drug boss kept wanting to meet with him and work things out—a sign, according to Hammond, that Fats suspected he was working with law enforcement.

But Hammond didn’t have long to worry. He was already on the FBI’s radar from the wiretaps, and police snatched him up on Aug. 15. While the charge for intending to distribute 10 grams of heroin might not be much for a first-time offender, there was a twist: his spray-painted gun. With the gun, what could have been a possession with intent to distribute charge suddenly became “using, carrying, and possessing a firearm during a drug trafficking offense”—a more serious, and violent-sounding, crime.

It wasn’t the first time Hammond’s dealing had gotten him in trouble, though he’d never been in so much legal jeopardy: In 2007, he claims that he narrowly evaded hooded assassins waiting for him in Congress Park. So he figured he might be able to skate out of the arrest: take a deal, perhaps avoiding jail time because it was his first offense, and lay low.

But there was a complication: his mother in Anacostia. If Hammond testified against Fats on charges of conspiracy to distribute heroin, he worried that there would be retaliation against her. FBI assurances that his mother could find a new place to live didn’t persuade him.

“‘We’ll move her’,” Hammond told me later, mimicking the agents. “Like she’s a cardboard person.”

The federal law enforcement machine that would roll over Hammond last summer first hit the streets 24 years ago.

Inspired by a plague of drug-inspired killings in the late 1980s, the District’s take-no-prisoners approach to the drug war started to take form in March 1989. That’s when the George H.W. Bush administration’s newly appointed drug czar, William J. Bennett, announced that Washington would be a proving ground for his high-intensity approach to drug enforcement, with federal and local agents organized into a rapidly deployed “strike force” aimed at the city’s drug gangs.

Washington, which was neither a major manufacturing area nor an entry point for drugs, struck some as a waste of federal resources. “This is the Potomac Fever approach,” one federal official told the Washington Post, as if anticipating the day FBI agents would be watching Hammond stuff heroin into a McDonald’s bag.

But Bennett saw the opposite, according to the Post, saying, “By God, something has got to be done.”

The federal approach scored a big hit a month later, when an 18-month investigation culminated in indictments against legendary D.C. drug kingpin Rayful Edmond III. Edmond’s elaborate supply network, which snaked its way from Colombian coca fields through the Los Angeles Crips until finally reaching its terminus in District drug markets, seemed like the perfect justification for federal intervention.

Today, Edmond’s in the witness protection program while in prison, and the city’s murder rate is at a 50-year low, but Bennett’s “something” is still playing out in the city. The drug war in Washington contributes to the estimated 60,000 Washingtonians who have criminal records, with all the complications that creates for getting a job. Many got caught for doing exactly what Hammond did: taking low-level positions in one of the only industries that would have them.

Law enforcement isn’t just going after hard drugs, either. A 2010 study gave Washington the dubious honor of the highest per capita marijuana arrest rate of all American jurisdictions. There’s an ugly racial element to the drug war, too, that doesn’t even take a particularly in-depth analysis to spot: In 2007, black Washingtonians made up 91 percent of marijuana arrests in D.C., as Washington City Paper reported in 2010.

All those arrests require more and more equipment and personnel. The Safe Streets Task Force that eventually surveilled Hammond and Fats is actually made up of three separate task forces, including one devoted solely to drug crimes. And while the wiretapped recordings in Fats’ investigation are extensive, those conversations likely didn’t come into federal hands cheap—a 2011 court report found that wiretapping a phone costs, on average, $71,748.

An avid reader of Malcolm X, Hammond understood that the unfairness of his situation extended beyond his lung medication. After he was arrested and charged, Hammond claimed he’d made a political statement at his detention hearing: “Fellow Americans, look at the new African-American slavery taking place in front of your eyes!”

It’s dramatic, and I haven’t been able to verify that it even actually happened. But it’s not that far from the truth.

We’re driving through Anacostia on Nov. 8, and Hammond’s pointing out the drug corners on Martin Luther King Jr. Avenue SE. Hammond had planned to take me to his mom’s house, where he’s been staying since moving from Baltimore. He was also supposed to introduce me to his friends today, so I could get a sense of whether he’s as “hot” as he claims, but when people think you’re working with law enforcement, introducing them to a white guy with a notebook is a tough proposition.

After his August arrest, Hammond was released without being charged. Instead, according to the FBI’s summary of Hammond’s interview, agents told him to “keep his contact and cooperation with law enforcement a secret.” The FBI also rehearsed evasive responses with Hammond, in case dealers asked him if he was working with law enforcement, according to the summary.

All the pat lines in the FBI’s handbook might not help him, though. In August, he ran into Fats’ cousin at the grocery store. She begged him to get out of D.C.

Ironically, having a reputation as a snitch means that Hammond might as well actually cooperate with law enforcement. “People think you hot,” Hammond says. “And now you gotta be hot if you wanna live.”

Even though it’s late in the afternoon, Hammond’s puffy eyes and baggy sweater make him look like he just rolled out of bed, which is exactly what he did. He’s terrified that the FBI is going to kick in the door of his mom’s house. Anticipating the agents, he’s been staying up at night and sleeping during the day.

At least he has things to think about. He wants to get a fashion degree—the heroin dealing was supposed to pay for that—to start a used-clothing store. He also dreams of creating a solar-powered grill. “My idea’s easy,” he says. “And I think it’d be more practical.”

Hammond’s also a big fan of books, both real and imagined. He peppers his biography with references to Think and Grow Rich, a 1937 self-help manual by Napoleon Hill, and he likes to explain his philosophy about drug-dealing with the title of a book he could write: The Art of Staying in Your Lane.

Just how he’ll stay free and alive enough to write a book and invent cooking appliances is where I come in. As I press him for more details about the mundane details of low-level heroin dealing, Hammond occasionally steers the conversation back to what he thinks I can do for him: namely, introduce him to lawyers. While he’s already had two court-appointed attorneys since his arrest, he thought they were too eager for him to cooperate with the FBI.

I tell him that publishing a story about him might get him some attention, although the chances of a legal nonprofit taking the case of a career drug dealer caught with a gun must be slim. “Put in there that I need help,” he says, gesturing at my notes.

Despite facing the problems of a serious drug dealer—federal agents breathing down his neck, concerns about his mother’s safety—Hammond insists that he’s not a “street guy.” But there’s one moment when his claims to run a bloodless, no-hassle drug business seem hollow. He’s talking about how he’d feel if someone lied about him on the witness stand. “If you get a conviction on somebody that straight-up lied on you, that’s enough to make me wanna kill somebody,” he growls.

Hammond will talk and talk about how he’s managed to avoid prison time for drug-dealing, despite having a prolific career in it: Don’t be flashy, don’t fight robbers. Don’t hang out with murderers, don’t try to kill people yourself. But there’s one question Hammond can’t answer: what it feels like when one of his heroin deals works well, and he’s suddenly $100 richer. He says he’ll need to think about it.

Hammond’s terrified that he’ll be prosecuted on organized crime charges, despite having little involvement with Fats’ alleged crew. With his sarcoidosis, 10 years might as well be a life sentence. At the same time, he’s worried about accepting a deal and leaving his mother behind. Idling his car in the parking lot of his mother’s church in Anacostia, he worries that his testimony would destroy her life. At the same time, though, working for the government is tempting. “If it wasn’t for my mother, man,” he says, his voice trailing off.

Hammond calls me late that night. He’s already started his nightly vigil for the FBI, and he’s been thinking about an answer to my earlier question. After decades of setbacks—the racism he felt as an electrician, his divorce, his lung disease, and his unemployment—he’s figured out why he keeps coming back to drug-dealing: “It’s a feeling of getting even.”

The D.C. Jail’s Video Visitation Room has only been open since July, but by November it’s already decorated with motivational posters, including one with a picture of a bridge that reads “SUCCESS.” Suddenly, Hammond pops onto the screen in front of me.

“I guess they wanted to show me they wasn’t playing,” he says.

He’s only been in jail for four days, but he seems skinnier. The FBI agents he had been waiting for finally came at 5 a.m. Nov. 13. Because Hammond was already up, he was able to keep his mother’s door intact and open it himself to let law enforcement in. Meanwhile, across the city, officers were arresting Fats and three other alleged members of his crew on charges of conspiring to distribute heroin.

“I’m sitting here with a bullseye on my head,” Hammond says. He’s convinced that his codefendants think he’s a snitch and have put a price on his head. He wants me to tell his lawyer to move him to the Correctional Treatment Facility, a privately run jail next to the D.C. Jail. Otherwise, he worries, he could soon find himself on the wrong end of a shank.

Unfortunately for Hammond, the only way he could likely make it to the Correctional Treatment Facility is if he agrees to turn state’s evidence. While the building was initially intended for inmates with medical problems, cooperating with the government could get Hammond enough leverage to get transferred. The benefits for his personal safety are obvious: Unlike the D.C. Jail, the Correctional Treatment Facility only houses low- and medium-security inmates. Still, Hammond seems confident that he would make bail days later.

The reality, though, has played out differently. In a Nov. 21 memorandum, a federal magistrate admitted that Hammond’s background—working as an electrician, living with his mother, and a spotless criminal record up to now—made him unlikely to commit crimes while on bail.

But other factors, including the gun and the three or four bullets that were in it, made him too dangerous. “A firearm was found in his possession,” the magistrate wrote, “dramatically increasing the danger he presents to the community.”

Since that hearing, the motions have dragged on ahead of a trial, whenever that will be. Hammond and his codefendants waived their right to a speedy trial, which should give their lawyers time to sift through the 36,000 phone calls, text messages, voicemails, and GPS alerts recorded by the wiretaps. Mutually agreeing not to press the legal right to a trial within 120 days of the charges being filed benefits the prosecution, too—in a motion supporting the move, prosecutors speculate that the delay could help convince some of the defendants to testify against each other.

Police finally arrested a sixth defendant in February—Jerry Levi Baptiste had managed to evade law enforcement, and thus put off pretrial motions, for an impressive three months. As for Fats, the U.S. Attorney’s Office claims that he could still be managing his alleged Kenilworth drug operation from behind bars.

If jail hasn’t changed Fats, though, it had an almost immediate effect on Hammond. In November, he told me that the prospect of leaving his mother behind doesn’t seem so impossible anymore.

“I don’t think she goin’ understand, but really, Will, I think it’s in my best interest,” he says.