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The Informant

It was one of the worst killing sprees in Washington history. The defendants stood accused of killing five young people and wounding eight. The case against them hinged on the testimony of their accomplice Nathaniel Simms. What made him break the code of the streets and help send his friends to prison?

The day will come, Nate Simms said on the stand, when his kids will ask the question he has already asked himself a thousand times: “Why? Why, Daddy? Why you do it?” Illustration by William J. Hennessy Jr./

In the Washington Highlands neighborhood of Southeast DC, up against the Maryland line, everyone plays his numbers at the market at Sixth and Chesapeake. The old drunks troll for change, and kids who never learned better call the Korean owner Jackie Chan. Out on the corner, the hustle and grind never stop, and every so often, because of a fake-diamond bracelet or for no reason at all, a spate of violence rips through the neighborhood like a tornado through a cornfield.

Sixth and Chesapeake is where Nathaniel Dwight Simms used to hustle—cocaine, marijuana, a little ecstasy—before March 2010, when he got tangled up in a bad thing, picked up an AK-47, climbed into the back of a minivan, and, along with some friends, gunned down a group of innocent kids on South Capitol Street.

Then Nate Simms did something really crazy: He snitched.

The South Capitol trial opened in February of last year. Five codefendants—Sanquan “Bootsie” Carter, his brother Orlando Carter, Jeffrey Best, Robert Bost, and Lamar Williams—stood accused of perpetrating one of the ugliest killing sprees in Washington history, a week in which five young people were shot to death and eight wounded.

The apartment building at 1333 Alabama Avenue soon after the shooting. Photograph courtesy of US Attorney’s Office for the District of Columbia.

For his role in the murders, though, Nate was not on trial. When he appeared before the jury in handcuffs and leg irons, it was as a witness for the United States government.

Assistant US Attorneys Michael Brittin and Bruce Hegyi had spent two years building a case against the South Capitol Five, but in the end it was only as strong as Nate’s story. A confessed drug dealer and child killer, he was the jury’s eyes and ears into the massacre.

I stopped by DC’s Moultrie Courthouse to hear the opening statements. The trial promised to be sensational: five men being tried en masse, each with his own lawyer and theory of defense. The violence had started over a bracelet, and for all the senseless reasons that young men pick up guns, this one seemed particularly insane. How could a cheap piece of plastic spark such bloodletting? And then there was Nate himself. What compels a gunman to break Southeast’s code of street justice—its omerta—and testify against his friends?

Two and a half months later, I had listened to more than a hundred witnesses and seen a thousand pieces of evidence, and I was still trying to answer those questions.

• • •

The testimony of Nathaniel Simms begins with a game of dice.

It was Sunday evening, March 21, 2010, and Nate, 26, was gambling near Sixth and Chesapeake when his luck started to skid. Nate had spent most of the weekend in jail for marijuana possession and was planning to use the last of his cash to take his girlfriend to a hotel that night. But the dice went cold and he wound up broke.

(Top) Jordan Howe, 20, was killed in the dispute over Sanquan “Bootsie” Carter’s bracelet. The Hi-Point .380 semiautomatic pistol that Bootsie used on Alabama Avenue. Photographs courtesy of US Attorney’s Office for the District of Columbia.

With his girlfriend’s silver Kia parked nearby, Nate agreed to give his friend Orlando Carter a lift across town. In the car, Orlando’s phone buzzed. It was his younger brother, Sanquan—known around the neighborhood as Bootsie—calling from an apartment complex on Alabama Avenue. He’d been robbed, he said. Someone had stolen his bracelet. “Man, we about to be on our way up there,” Orlando assured Bootsie.

Unlike Nate, whose rap sheet included just a few petty drug offenses, both Orlando, 20, and Bootsie, 19, had extensive juvenile records. (They’re sealed, but prosecutors have called the latter’s “truly alarming.”) As an adult, Bootsie was picked up for armed carjacking and later convicted on lesser gun charges. Orlando was rumored to have been involved in the 2009 murder of his cousin over a drug beef, and in 2011 he would attack a fellow inmate at the DC jail, ransacking his cell and stabbing him in the head and neck.

From the silver Kia, Orlando called his godmother, Ma, who lived nearby. “Ma, bring me my bitch,” he said. When she didn’t appear, he darted into her house and reemerged with an AK-47 assault rifle tucked under his jacket.

Nate, Orlando, and another friend, Jeffrey Best, jetted to the apartment of Lamar Williams. Lamar came outside, guns in hand. He gave Nate a Hi-Point .380, a sleek semiautomatic pistol, and slipped into the back seat with a 12-gauge pump-action shotgun.

Orlando nodded to the .380 on Nate’s lap: “Bootsie is gonna work that for you.”

“Who gonna work this big-ass joint?” Jeff wanted to know, and Lamar showed him how to operate the shotgun. “Oh, yeah, I love this shit,” Jeff said, bouncing in his seat. “I love this shit.”

Lamar left the crew and went back inside. Orlando took off his signature red Helly Hansen jacket, stuffed it into the trunk, and donned a black one instead.

“These motherf—-ers robbed my little brother,” he said. “They gonna see.”

• • •

Wedged between Malcolm X Elementary and the Congress Heights Metro station, 1333 Alabama Avenue is a low-slung red-brick apartment building. Apartment 107 belonged to Ja’mya Wilkins, who often let friends party there, including 20-year-old Jordan Howe, who lived one floor up with his mother and aunt.

Jordan and his friend Bootsie showed up that Sunday night with two girls in tow. Bootsie showed Ja’mya his bracelet—a cheap piece of costume jewelry, several of its plastic diamonds missing—as he walked in. “He asked did I like it,’ ” Ja’mya recalls. “I told him it was icy.”

A small crew lounged on couches, drinking Amsterdam gin and papaya juice, passing around a joint. After a while, Bootsie got up and led the girl he’d brought, Akeela Johnson, into the spare bedroom. Jordan followed with Akeela’s friend Keya Harrington. He gave Keya a playful push backward and locked the door behind him. Bootsie and Akeela had claimed the room’s bare mattress, so Jordan and Keya had sex on the floor beside them. When Jordan finished, he walked back into the living room and told his godbrother and best friend, Andre Morgan, to take a turn with Keya.

It was only later, as she got dressed, that Keya spotted Bootsie’s bracelet atop a pile of his clothes. He didn’t notice her trying it on, and she tucked it under the sleeve of her leather jacket. Bootsie walked the girls to the parking lot and promised to call them soon. On the way home, Keya pulled back her sleeve to show Akeela her new icy bangle.

In the apartment, the night took a quick turn for the worse. “Someone got my motherf—-ing bracelet!” Bootsie yelled, but a search of the bedroom turned up nothing. Ja’mya returned from a walk to find him “rampaging through things.” If he couldn’t calm down, she told him, he’d need to leave.

Bootsie went upstairs to Jordan’s apartment, where Jordan was saying goodnight to his mother, Diane Howe. The boys had played Pop Warner football together as kids—the Fighting Irish, with Howe acting as team mom—and Bootsie had dated one of Jordan’s cousins.

“Man, nobody got that fake bracelet,” Jordan said. But Bootsie, notoriously short-fused, used Andre’s phone to call his brother.

“They stole my shit,” he told Orlando. “Bring everything.”

  • The Defendants

    Orlando Carter, 20

    According to prosecutors, he was the ringleader. Photographs courtesy of US Attorney’s Office for the District of Columbia. Next >>
  • The Defendants

    Sanquan “Bootsie” Carter, 19

    Orlando’s brother. The fake-diamond bracelet was his. Next >>
  • The Defendants

    Jeffrey Best, 21

    He was a talented athlete but had dropped out of school. Next >>
  • The Defendants

    Lamar Williams, 21

    He supplied his friends with guns, then parted ways. Next >>
  • The Defendants

    Robert Bost, 21

    He joined up with the crew after Orlando was shot. Next >>
  • The Defendants

    The men rented a Town & Country minivan for the South Capitol Street shooting after Jordan Howe’s funeral. Back to Start >>

Just after midnight, the silver Kia careered into the parking lot off Alabama Avenue. Bootsie hustled over.

According to Nate, Bootsie reached through the window and took the .380. He wheeled around and began patting the pockets of the partygoers, now gathered on the steps outside. Behind him, on the edge of darkness, Orlando appeared with the assault rifle. Jeff flanked him, shotgun in hand.

Tempers flared, and a shouting match broke out. Bootsie jumped back off the steps. “Y’all ain’t gonna gimme my bracelet,” he said. “F—- it. Go ham”—as in “go hammer.” The cool night exploded in gunfire. A spray of bullets raked the car where Jordan was sitting with his cousin Kalisha and the building behind it.

On the steps, 15-year-old Victor Kevin Martin was shot through the left leg. He staggered inside to his sister’s apartment and collapsed in the bathroom. Tavon Lambert, 22, who was hit in the calf and hip, cut through a hole in the fence and ducked into the alley behind the building. Ja’mya Wilkins sprinted into the building’s laundry room and hid behind a dryer. She ventured out a few minutes later to hear Andre screaming, “They killed Jordan!”

In fact, Jordan was still alive when Ja’mya reached the car, but he was losing blood fast. A bullet had ricocheted through his pelvis, severing an artery. Ja’mya cradled his head in her lap. “He asked me why everything was getting dark,” she recalls.

Jordan’s mother charged outside. “Don’t leave me,” Diane Howe told her son. “You gotta promise you not gonna leave me.”

Andre Morgan tried to drag Jordan’s body out of the car. Unable to do so, he fled the scene covered in his godbrother’s blood. He knew where the Carter brothers lived. “I wasn’t gonna wash my hands till I caught my vic[tim],” he says.

• • •

The shooters sprinted back to the Kia, and Nate drove them to the nearby townhouse of a Carter family cousin. “I’m gone,” Nate said as the others got out. He was still hoping to rendezvous with his girlfriend.

How Plea Bargains Work

There are two basic types of plea agreements negotiated by prosecutors and defense lawyers. In the first, the defendant pleads guilty in exchange for certain concessions, such as dropping some charges or a commitment by prosecutors to ask the judge for a reduced sentence.

The second type also includes a cooperation agreement, which requires the defendant to assist prosecutors in their investigation—as Nate Simms did. The defendant must promise to tell the truth and agree to be available for meetings and to testify in court. If the defendant fails to meet any of these requirements, prosecutors are free to rip up the deal.

Prosecutors are guided by a US Attorney’s manual that describes general criteria for working out plea bargains, but they usually have a lot of discretion. The main rules are that they must seek a plea for the most serious, readily provable charge against the defendant and that they must be honest when calculating sentencing recommendations. Prosecutors take into account a defendant’s willingness to cooperate, his or her criminal history, and individual conduct when assessing the terms of a deal.

A plea agreement, however, doesn’t equal a guarantee of leniency. In the end, it’s up to the judge to decide the defendant’s punishment.

“You don’t need to go nowhere, ’cause the car is hot,” Orlando said. “You need to come inside with us.” They wrapped the long guns in coats, Bootsie pocketed the Hi-Point, and the boys snuck in the back door. They spent the night on the floor. Nate left before dawn, and the others followed soon after.

Two days later, on Tuesday evening, March 23, Orlando Carter was standing near Sixth and Chesapeake when Jordan’s half brother, Marquis Hicks, walked up on him with a chrome revolver, stuck the barrel in his face, and pulled the trigger. The first two chambers were empty, but the third and fourth were not. Orlando was shot in the head and shoulder, but instead of finishing him off, Marquis panicked and ran. Orlando survived, a terrible vengeance now burning in his heart.

Nate got a call from Jeff: “You need to get over here,” he said. “Orlando just got shot.” Nate picked up Robert Bost, a friend of Orlando’s who’d seen the attack. By the time they met up with Jeff, there was more bad news: Bootsie was in jail. He’d been picked up by the cops that morning. They needed to hide the guns and lie low.

Orlando greeted Nate and Jeff the next morning at his mother’s house with his arm in a sling and a bandage covering the side of his face. “Man, those niggas tried to do me in,” he said. It had to be Jordan’s people. “We gonna f—- that funeral up.”

The crew—which had grown to include Robert Bost—needed more firepower. They needed to rent a car. And they needed to divine the date and time of Jordan’s funeral.

That last piece of intelligence fell into place the following weekend, when Nate and Lamar picked up two girls “from the other side”—Jordan’s people—and took them to a Red Roof Inn. They stayed only a few hours, but that was long enough for Lamar to overhear a conversation about the upcoming service.

On Sunday morning, Orlando got a text from Nate’s phone: “Funeral on tuesday.”

• • •

Nate spent Tuesday, March 30, checking in with his probation officer and raising a little last-minute cash for the big night.

A high-school dropout with kids by two different women, he had driven deliveries for Domino’s for a while and worked the counter at Wendy’s. Mostly, though, he hustled and scraped by. When business was steady, he might pull down a couple hundred bucks a day.

Nate had grown up the youngest of four children. His mother was a correctional officer who raised her family on a single income. His father was a drug addict and vagrant.

Nate was no stranger to street violence. His older brother had been paralyzed at a young age by a stray bullet, and Nate himself was shot in the knee in 2004. He spent two weeks in the hospital and never regained full use of the joint.

As a teen, Nate tangled with his mother’s live-in boyfriend, a disciplinarian with a nasty temper. By the middle of high school, the beatings got so bad that he moved in with his grandmother. He dropped out of school after junior year to deal drugs full-time.

Nate’s grandmother’s health was failing, and when she passed away in 2002, an aunt kicked him out of the house. Rudderless and broke, he depended on lovers for a place to sleep. At one point, he bought a car at auction and lived in it for six months.

Prosecutors would later paint Orlando as the ringleader of the South Capitol crew, Bootsie as the hot-tempered instigator, and Nate as a hapless flunky, “without meaningful family ties, and in a constant search for affirmation.” Nate “mistakenly” thought he’d found that affirmation among Orlando’s crew—and once he was in, he couldn’t back out.

“You can call it afraid,” Nate testified. “You can call it whatever you want.”

• • •

Early Tuesday evening, a rented Town & Country minivan pulled up to the Seventh Street apartment of Martaraina Salazar, a young woman Nate was sleeping with.

Nate had been keeping Rob’s .45, Jeff’s Glock 17, and a bag of bullets inside the apartment. He tucked the pistols into his waistband, said goodbye to Martaraina’s two kids, and promised to pick up a bar of soap for her on the way home. He wouldn’t be gone long.

Orlando, Jeff, Rob, Lamar, and Nate headed to Lamar’s apartment, where Orlando told him to fetch the AK-47 and an extended clip. He wanted big firepower. As before, Lamar split ways with the crew after furnishing the weapons. Meanwhile, Orlando made a series of calls to a “mystery spotter,” whose identity prosecutors have never made public.

Orlando turned into the Wingate Apartments complex. “I’m gonna send my men in,” he said over the phone. Jeff and Rob slipped out of the car. It was beginning to grow dark.

The Wingate Apartments surround a grassy quad with a pool and playground; a small hill rises behind the rec center. It was on that hill that 17-year-old Tavon Nelson—Tatum to his mother, on account of being so chubby at birth, like a sack of potatoes—was standing just before sunset when two masked men entered the yard. Tavon was carrying a gun and, recognizing an armed robbery, reached for it as his assailants approached.

Nate heard a volley of shots and watched his friends come sprinting back to the van—Jeff first, followed by Rob. They were breathing hard and, inexplicably, empty-handed. Jeff’s Glock had gotten stuck in his coat, he told Orlando. He’d freed it just in time. “I hit his ass,” he said.

“Yeah, you hit him,” Rob said, “but I finished him.”

Tavon’s gun, meanwhile, was still lying on his body. Orlando was furious—the whole point had been to score another weapon. He had no choice but to peel out, though. In this part of town, the cops were never more than a minute away.

  • Lennox Jones and Nardyne Jefferies speak to reporters
    after the death of their daughter, Brishell Jones.

    Photograph by Nikki Kahn/Getty Images. Next >>
  • Brishell, 16—who was shot in the head and shoulder—had dreamed of owning a restaurant.

    Photograph of Brishell courtesy of US Attorney’s Office for the District of Columbia. Next >>
  • Brishell’s funeral in April 2010 was at Canaan Baptist Church in Northwest DC.

    Photograph by Nikki Kahn/Getty Images. Back to Start >>

Orlando had word that some of Jordan’s people were gathered after the funeral on a corner of South Capitol Street where they often hung out. He eased the van down the far side of the street and motioned out his window, to a small crowd wearing REST IN PEACE, JORDAN shirts. “Nate,” he said, “pick up that chopper.”

Orlando bucked a U-turn and rolled back up South Capitol. “When I pull over, have them guns hanging out the window,” he said. The van slowed, drifted to the curb, and stopped. “I lifted up the AK-47,” Nate testified. “I put it out the window. I leaned back ’cause Jeff was reaching across me, and I pulled the trigger. I ain’t even look. I just pulled the trigger.” Jeff, Nate, and Rob sprayed the crowd with gunfire. Hot casings rained onto the pavement.

Sixteen-year-old Brishell Jones caught a bullet in her right temple. It exited through her skull and passed through her shoulder like a skipping stone. Eighteen-year-old DaVaughn Boyd was shot in the back. Nineteen-year-old William “Marley” Jones III dropped to the ground with holes clean through his arm, leg, and forehead, a program from Jordan’s funeral still folded in his coat pocket. The way he fell back on the grass, his dreads were tangled around his face as if he’d been dancing.

Six others were wounded. Marley’s girlfriend, Tierra Brown, was hit below her knee; his little brother, 15-year-old JaBarie Smith, was hit in the right leg. Four more bullets found the brothers Kevin Attaway and Jamal Blakeney—Kevin would arrive at the hospital without a pulse and lose the front of his skull to an emergency craniectomy. Darrick Lanier was eating a steak-and-cheese from the carryout when a round went through his wrist. Seventeen-year-old Ra’Shauna Brown, Brishell’s best friend, was listening to her iPod when the grass started smoking. She came to on the ground, blood streaming from her shoulder and leg. Her 911 call was one long scream.

Orlando didn’t speed off. He lifted his mask and surveyed the damage: 15 seconds, 20. “Just looked,” Nate testified. “Just looked.”

Moments after they pulled away, Orlando saw a cop car waiting at a light, facing them. Orlando leaned back in his seat, trying to appear casual. It didn’t work—all of the Seventh District was on the lookout for the silver Town & Country—and the cruiser hit its siren. Orlando sped past the squad car and headed for I-295. “They comin’,” he said, stealing glances in the rearview mirror.

As the line of patrol cars chasing the minivan grew, Jeff asked Nate for a Newport. The two men smoked a last cigarette.

Nate carried two cell phones, and as the van sped back into Southeast, he used one to call Martaraina, at home with her kids, still waiting for him to return with her soap. “I did something stupid,” he said. “Open the door. I be down there.”

He used the other phone to call his girlfriend, Brittany Young. “I messed up,” he told her. “I did something stupid that I shouldn’t have never did. I probably won’t see you no more. And I’m sorry.” As she begged him to tell her what was happening, he slipped the phone, still on, into his pocket.

“We gonna have to get out and run,” Orlando announced. He pulled the minivan into an alley, slowed to let a cop car come alongside it, and then sideswiped the cruiser, trying to buy them a little space. He hit the brakes. The doors flew open.

Jeff, a star athlete for whom there was once talk of playing college basketball, took two steps and seemed to disappear, leaving behind only his jacket. Rob fled in the opposite direction and hopped a retaining wall behind Paramount Baptist Church, where later even a police dog couldn’t pick up his scent.

Police tackled and cuffed Orlando less than half a block from the van. Nate, bum knee and all, headed for Martaraina’s house three blocks away. He was on home turf. With an officer giving chase and Brittany listening on the phone, he tore through the alleys toward Chesapeake Street, scrambling over fences and across lawns. A squad car howled into his path, cutting him off. He lay down on the ground and placed his hands over his head, as if to pray.

• • •

Grief turned to rage in Southeast before the blood was dry on the pavement, and whatever detectives could do to round up evidence, they couldn’t do it fast enough. Three men were in custody: Nate Simms, Orlando Carter, and a 14-year-old boy named Malik Carter who’d been picked up near the bailout and identified by two police sergeants as the driver of the minivan.

teen getaway driver is brother of se shooting suspect, Channel 9 announced on its website, citing anonymous sources who claimed that the boy was “remorseful” and had been “duped into giving his brother and friends a ride.”

The prosecutors assigned to the case—Michael Brittin and Bruce Hegyi—were struggling to cobble together even a basic narrative of the crime. “When you get an investigation like this,” Brittin says, “you very much want to see the big picture, but you can’t, because it’s too early. All you know is you’ve got bodies strewn all about the street.”

They got a breakthrough when Jim Williams, a veteran criminal-defense lawyer, contacted their office. His client, Nathaniel Simms, was willing to talk.

Incredulous, Hegyi and Brittin hurried to police headquarters. They thought highly of Williams, but his client had to understand that debriefing with prosecutors was an all-or-nothing proposition.

Nate would screw himself royally by withholding any details or backing out later. If he was going to sing, the government was going to make him do Wagner.

• • •

In fact, Jim Williams was as surprised as anyone. He’d met Nate a week earlier in the crowded jail bullpen. “I’ve been asked by the court to try to help you,” he told his client, slipping him a card.

When they sat down a few days later, Williams launched into his standard spiel: Don’t talk on the jail phones, don’t discuss your case with anyone. “And I think he was hearing, ‘Blah, blah, blah, blah,’ because he turns to me and says, ‘Man, what can I do to make this right?’ ”

Williams couldn’t recall working with a client whose first instinct wasn’t to minimize his exposure. But he did as asked and arranged a meeting with the prosecutors.

A team of investigators crammed into a small conference room at police headquarters. One of the first things Nate told them was perhaps the most surprising: Malik Carter, the 14-year-old, had nothing to do with the shooting. The government’s working theory—the kid’s name was Carter, after all, and he’d run at the sight of the cops—now had an ugly hole in it. “Mike Brittin’s jaw was on the floor,” Williams says.

Nate gave up Jeff, Rob, and Lamar. His mind was sharp, good with times and places, addresses and phone numbers.

“We’re testing him,” Hegyi says. “We know he’s going to get cross-examined hard. He’s no good to us if he goes up and falls apart like a piece of wet tissue paper.”

The prosecutors were won over. “When he started talking about that AK-47,” Hegyi says, “the tears were just streaming down his face. He said, ‘It was me. It was me. I did it.’ ”

Nate was pulled from the DC jail and spirited out of the District. The US Attorney’s Office, meanwhile, was preparing to exonerate Malik Carter. Concerned that the announcement would throw Southeast into a tailspin—if the police couldn’t lock this thing down, someone was going to pick up a gun and settle it himself—Hegyi and Brittin were eager to make more arrests.

By late April, Jeff, Rob, and Lamar were all in custody. Prosecutors approached their attorneys with talk of a plea deal; they wanted a second cooperator, to make a tighter case.

Lamar was their best candidate. He had never pulled a trigger, and he had a shorter criminal record than the others. A talented drummer and disciplined student, he’d graduated from high school in 11th grade and gone on to Shaw University in North Carolina. He might have become something. But when you’re 21 years old, a term of 30 or 40 years can look like a death sentence. Instead, you take your chances, seal your lips, and hope to draw a friendly jury.

  • The AK-47 used by Orlando Carter on Alabama Avenue and Nate Simms
    on South Capitol Street.

    Photograph courtesy of US Attorney’s Office for the District of Columbia. Next >>
  • A vigil at the scene of the South Capitol Street shooting.

    Photograph by Sarah L. Voisin/Getty Images. Next >>
  • Ronald Machen Jr., US Attorney for DC, and Police Chief Cathy Lanier at a press conference
    outside the courthouse.

    Photograph by Matt McClain/Getty Images. Back to Start >>

In late April, less than a month after his arrest, Nate Simms walked into DC Superior Court and pleaded guilty to five counts of murder plus two counts of conspiracy to commit murder. Such pleadings are typically done under seal, but with the media frenzy over Malik Carter’s wrongful arrest, prosecutors hoped to spin a counter-narrative. “There was a lot of acid churning in the stomach,” Hegyi says, “because we just put a target on his back.”

Keeping a cooperator alive is no small feat. The jailhouse mantra “Snitches get stitches” is less an observation than a promise. Hegyi recalls working a Seventh District murder some years ago, in which a known cooperator was picked up on an unrelated misdemeanor and hauled to DC jail. Had prosecutors been notified, they might have stepped in to protect him. They weren’t told, and he was stabbed to death.

If Nate were murdered before the trial, prosecutors wouldn’t be able to use any of his sworn statements unless it could be shown that the defendants were involved in his killing. (The Sixth Amendment’s “confrontation clause” guarantees a defendant the right to face his accuser in court.) At one point, a jailhouse rumor circulated that somebody in DC, perhaps Orlando’s father, was looking for guys who would volunteer to get locked up with Nate and do a hit on him.

At his guilty-plea hearing, Nate asked to wear a hood in the courtroom. The government denied the request.

• • •

Nearly two years later, when the star witness of South Capitol appeared three weeks into the 2012 trial, the gallery in Courtroom 316 was a zoo. After so many days of crime-scene photographs, bagged evidence, and expert pathologists, spectators and jury alike had begun to get restless. Now the drama they were watching finally had its leading man.

Stone-faced US marshals stood at every door. TV news personalities, wire-service reporters, and a sketch artist camped out in the best seats. The victims’ families filled in behind them. The defendants sat in their Sunday best—cardigans, pastel oxfords, and bow ties. They chatted and smiled, looking for all the world like Howard University fraternity brothers awaiting an invitation to dance.

Nate wore a navy jumpsuit and leg irons. He was balding, and his ears stuck out from his hangdog face. Leaning into the microphone, he drawled a soft “G’mornin’.”

From the stand, Nate unspooled his story. Shaped by Brittin’s questions, it had a familiar arc: a ne’er-do-well who’d hit bottom, committed an unspeakable crime, and now wanted to make right.

“I was a sucker,” he said, choking on his tears. “People talk about ‘You’re a sucker for sitting on this stand.’ I was a sucker for not stopping what happened.” He continued: “The day will come when I gotta explain to my kids that Daddy can’t see them no more because he took somebody else’s babies away from them.” They would ask him the same question he had asked himself a thousand times: “Why? Why, Daddy? Why you do it?”

Sanquan Carter’s lawyer, Arthur Ago of DC’s Public Defender Service, was waiting to flay Nate on cross-examination.

I liked to watch Ago during the trial because his body language told me how things were going. On good days, he’d scribble furiously on his legal pad, bobbing his head like a robin and bouncing his leg so hard the table shook. On bad days, he’d shut his eyes and pinch his nose, as if awaiting a migraine. (None of the defense lawyers involved in South Capitol would speak to me for this article, nor would their clients.)

Ago pointed out that if Nate provided “substantial assistance” to the government, the prosecutors would ask his sentencing judge to go easy on him. Instead of serving five life sentences—one for each murder—Nate might do 25 years and walk.

Ago hauled out Nate’s grand-jury testimony—some 170 pages—and read aloud all the instances where he seemed to embellish his story or make up details. Here was a man, Ago argued, who would tell the government anything it wanted to hear. In jailhouse phone calls, Nate was recorded telling his girlfriend, “I plan on walking outta here at the end of the month. It’s a fight. And I plan on winning that fight.”

Thomas Heslep, Lamar’s attorney, accused Nate of being a con man who could cry on cue. Todd Baldwin, Rob’s lawyer, wanted to know why he hadn’t gone to the cops after the first shooting, on Alabama Avenue. If he’d wanted out, why hadn’t he turned to the police for protection?

Nate laughed at the suggestion. In Southeast, he told the jury, “the debt of witnessing a murder is not repayable.”

After five days of testimony, Nate stepped down from the stand. He shuffled past his friends and exited the courtroom, head held high, tears drying on his cheeks.

• • •

The sight of a father who has buried his son is a painful one. Norman Williams, Jordan Howe’s dad, was a leonine man made volatile by grief, and for 21⁄2 months he lurked in the gallery of Courtroom 316, eyeing the defense lawyers, muttering loudly, making the marshals uneasy.

Of Nate, Williams said: “He was dancing with the devil, and when you dance with the devil, you can’t just walk away and say, ‘I’m sorry.’ ” He went on: “He couldn’t get out. He was in too deep.”

Brishell Jones’s grandmother Patricia Jefferies wore a shirt with her granddaughter’s face on it until the judge forbade it. Jefferies would bring cupcakes for the prosecutors, peppermints for reporters, and a box of Kleenex for herself. She led a sorority of aunts and family friends who watched for any sign of injustice. Once, they caught a juror texting. Another time, they spotted Orlando winking and making kissy faces at a female witness. “Jesus had his Judas,” she’d say. “These boys are ours.”

Not every fact in a trial comes out under oath. Some get handed around by grandmothers who miss their babies. Here are some facts that don’t appear in any transcript: Brishell Jones’s favorite movie was The Color Purple. She loved Trinidad and Tobago, where she summered with her father’s family. She was stubborn and always right. She might have grown up to be a chef—she dreamed of owning a restaurant.

Jefferies talks to a picture of her granddaughter every night before bed. “Think of all that’s been stolen from us,” she says. “No prom. No high-school graduation. No college. No wedding day.”

• • •

In July, I paid a visit to another grandparent who misses his baby. Jefferson Best Sr. was sitting on his porch when I arrived, trying to escape the midday heat.

Best did everything right: He worked an honest job, driving a big rig around town; served as a deacon in the church; and ran his home like a quartermaster—no drinking, no cursing, no girlfriends, no leaving after dark. He and his wife, Ida Mae, had six kids, and when their adult daughter Laverne moved back in with her two young sons, Jefferson and Ida Mae helped raise them, too.

“They’re a tremendous family,” Hegyi, who still drops in on the couple, says. “They’re wracked with guilt, and it’s like, au contraire, you guys did everything you can. You need to let yourselves go. I’m quick to point out, hell, I had an uncle in prison. Just because somebody related to you went to prison, that has nothing to do with you.”

Best keeps a glass case of his grandson’s trophies in the living room: Hendley Elementary School Champions, 1997. MVP, Capitol Hill Basketball, 11 and Under. As a teen, Jeff was a standout athlete, less than six feet tall but quick on the basketball court and football field. His grandfather sometimes drove the team bus so he could attend games. He says that by Jeff’s senior year, scouts from Georgetown were calling: “Jeff used to burn them boys down, I tell you.”

But Jeff dropped out before graduation. “He found something else better,” Best says. Soon he was hustling on the corner and spending nights with his girlfriend across town. He kept a room in the basement and still knew better than to walk on his grandfather’s grass, but the boy was on his own.

Best hasn’t seen his grandson since Jeff was arrested. When the police came with a warrant, they knocked the door in, roughed up the drywall, and turned the place upside down. Someone from the US Attorney’s Office promised to repair the damage—“He said, ‘Well, don’t y’all worry about it. I’ll see about that door for you’ ”—but Best never heard from him again. Eventually, the old man bought a new door himself.

He refuses to go to the prison with Jeff’s mother. His heart can take only so much.

• • •

The government took seven weeks to argue its case. Hegyi and Brittin lined up experts in DNA, ballistics, and phone records. They called dog handlers, bereaved mothers, and Michael White, who was buying hot-dog buns on South Capitol when he heard “firecrackers” across the street. “All I could see was bodies, just lying there,” he testified. “Bodies lying all over top of each other.” For a time, it seemed as though every crime-scene technician on the force could be found in the court’s antechamber, waiting to take the stand.

The defense required just a week. Jeff alone testified on his own behalf. He hadn’t been at Alabama Avenue, he said—no way he could have snuck past his grandfather—nor had he ever set foot in a silver Town & Country. The reason he’d been seen running scared the night of South Capitol was that he’d had drugs in his pockets. After he was arrested, he said, he felt like killing himself: “My mother, she didn’t want to see me behind no glass.”

It took the jury eight days to deliver a verdict, during which the prosecutors began to drink more Scotch than usual and worry about the possibility of a mistrial.

Hegyi told me that, in the ’80s and ’90s, DC juries often hung 11-1, 10-2, even in the face of overwhelming evidence. “Jurors, as a population, were saying, ‘We don’t want to send another young black man to prison.’ ”

Then a note, and on a Monday morning in May the jury returned. The foreman rose and did his duty.

Sanquan, Orlando, Jeff, and Rob—guilty on all counts. The friends sat listless as the verdicts were read, as if watching a film whose ending they already knew. In the gallery, Brishell Jones’s family clutched hands, whispered prayers, and fanned themselves to keep from fainting. Jordan Howe’s mother wept.

Lamar Williams was acquitted of crimes related to Alabama Avenue and convicted on lesser charges than the gunmen on South Capitol Street. Jeff smiled at the news. As the defendants were ushered out, hands behind their backs, he was still smiling.

• • •

The South Capitol Five were sentenced on a crisp Tuesday morning in September. So many family members wrote impact statements that it took until after lunch to read them all aloud.

A few called for understanding. “I’m in the process of trying to forgive them,” wrote Tierra Brown, whose boyfriend was killed on South Capitol Street, “because I don’t want to carry this burden anymore.”

Most did not. “Seeing these offenders face to face made my blood boil,” wrote one mother, “because I want to snatch their throats out of their neck and watch them bleed to death.”

There were poems and Little League baseball cards and stories of lives interrupted. “I now know how much Brishell’s brain weighs, her heart and lungs,” her mother wrote.

Orlando, Jeff, and Rob were sentenced to life in prison without the possibility of release. Sanquan, present only at the Alabama Avenue shooting, was sentenced to 54 years. Lamar, never a gunman and convicted on lesser charges, was given 30. (All five have appealed their convictions.)

“There’s no winners,” said Adam Schwartz, a young prosecutor assigned to help Heg-yi and Brittin at trial. “We go on to the next case. Everyone’s lives are destroyed, the defendants and the victims’ families. That’s the nature of a murder case. There’s no happy ending.”

• • •

Locked in solitary confinement, Nate awaited his own ending.

His sentence would set a precedent. He had been “pathologically truthful” with detectives, taken a plea in open court, and performed well on the stand—if he didn’t get a big break, what kind of message would it send to future cooperators?

The prosecutors spent weeks drafting their sentencing memorandum. “You had an agreement with us, and you held up your end,” Hegyi said. “We will hold up our end.”

Fairness is a funny thing, though. “If you could say to the victims’ families, ‘You get to pick the sentence,’ it would’ve been execution,” says Jim Williams, Nate’s lawyer. “If we can’t do that? Life without parole.”

The Monday before his October sentencing, Nate and Nardyne Jefferies, Brishell’s mother, met for the first time. Jefferies had been asking prosecutors to arrange the sit-down since 2010, but they’d declined, fearing it could complicate his testimony. On the stand, Nate had tried to address her: “I killed a 16-year-old little girl, and I see her mother right there and I’m sorry,” he said before being admonished by the judge. “I’ve been wanting to tell you that for the longest. I’m sorry, Ms. Jefferies.”

When Jefferies came to visit, she showed Nate photos of Brishell and talked about the woman she might have become. “You didn’t just murder my daughter,” she said. “You murdered generations of my family. Because this is the only child I’ll ever have. Now my whole life stops with me.”

“He wanted to apologize,” Williams, his lawyer, says. “He wanted to show her that he’s not the monster the other guys are.” Jefferies didn’t offer forgiveness, but later she asked Williams how she and Nate might stay in touch, and she gave him her cell-phone number.

• • •

After much deliberation, the prosecutors requested a 60-year sentence, with all but 25 years suspended.

Jefferies was frustrated by the government’s calculus. “I just feel like it’s an insult,” she told the sentencing judge, Michael Rankin. In the courtroom, she showed Nate one last picture of Brishell: her autopsy photo, with half her face blown off. “This is what is burned in my memory,” she said. “This once beautiful, vibrant life. Head wide open.”

When Nate was allowed to speak, he had no explanations, only apologies. “I pray for forgiveness every night,” he said. “And I still hold that guilt, because I feel like God don’t forgive murderers.” His mother and sister, sitting behind him, wept.

Judge Rankin agreed that 25 years hardly felt like justice. But even in a “twisted system,” he said, we must strive to create a more perfect world, where kids in Southeast aren’t afraid to talk to the police.

He gave Nate 25 years.

“One other thing,” he said, fixing Nate with a heavy stare. “If you really believe that your God doesn’t forgive, you’re praying to the wrong God. You might want to give that some thought. My God forgives.”

• • •

Nathaniel Simms will now disappear. This winter, he was moved to a secret location for at-risk cooperators.

He’ll be in his fifties when he gets out, a middle-aged man with no work history, no savings, and no intimates. His son, Naquan, will be just shy of 30—a little older than his dad was when he gunned down a group of kids on South Capitol Street.

Nate has applied for the witness-protection program. If accepted, he may never be allowed to return to Southeast or to contact his family, even by phone. He will be, to everyone but himself, a man without a past.

Kevin Charles Redmon is a journalist living in DC’s Petworth neighborhood. He can be reached at

This article appears in the March 2013 issue of The Washingtonian.

  • Maya Chung


  • Lindsay

    "Not every fact in a trial comes out under oath. Some get handed around by grandmothers who miss their babies. Here are some facts that don’t appear in any transcript: Brishell Jones’s favorite movie was The Color Purple. She loved Trinidad and Tobago, where she summered with her father’s family. She was stubborn and always right. She might have grown up to be a chef—she dreamed of owning a restaurant."

    This section was eloquently written. Sometimes its the facts outside the immediate story that resonate best with readers.

  • Indigo Mordant

    No, they should be forced to labor for the benefit of the people and the country without compensation or any chance of enjoying the fruits of such work till the day their backs give out. A fitting punishment that hits the American Dream right in the gut.

  • Raj

    life a a dc govt employee is far to good for these thugs

  • Lynn so. freaking sad. My god. I've lived and grow in affluent neighbor hoods where the closest we got to violence were hearing about rumors of someone carrying a guy, from the friend of a friend of a god.

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