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At 10:20 a.m. on June 14, 1999, a Metropolitan Police Department detective and federal agents wired up a confidential informant and dropped him off in Congress Park with simple instructions: find “LT” and get him to talk about who shot Ronnie Middleton and Sabrina Bradley.

“LT” was Antonio Roberson, and he’d bragged about killing the couple a year earlier in Congress Park, the informant told police. There were different theories over the years about why the couple was killed, but they all focused squarely on Middleton, who prosecutors say was a hitman for local drug kingpin Tommy Edelin. Bradley, a mother of two and Middleton’s girlfriend, just happened to be there. “Collateral damage,” as one prosecutor put it.

At 10:40 a.m., the recorder was turned off. The undercover operation was quick and, by any measure, a success. “In what was described as a very brief discussion, the source advised that Roberson engaged the source in conversation regarding the captioned shooting,” a detective wrote. “The source stated that Roberson openly discussed his involvement in the incident, including firing the shots that took the lives of Middleton and Bradley.”

It’s been nearly two decades since the slayings. The case is closed. Roberson is long since dead; so is another purported participant in those killings, Antoine Draine. And yet a few months ago, MPD’s Office of General Counsel, acting on a directive from the mayor’s office, told the department’s homicide branch to search its files for the old tape.

The search was the result of David Wilson’s Freedom of Information Act request and subsequent appeal. In D.C., he was known around Congress Park as “Cool Wop,” but now he lives in a federal prison in Pine Knot, Ky., after he was convicted for driving the getaway car in the Middleton and Bradley murders. But he insists that whatever Roberson said on that tape 16 years ago will exonerate him.

“That evidence has been out there since ’99. It’s case-solving evidence,” Wilson said. “I know it was transmitted, and I want to know what was said because I know it exonerates me… I don’t think that the MPD is that negligent or careless, especially with a homicide where people lost their lives.”

Prisons are filled with inmates like Wilson doing life or close to it. Many of them have ample time to file open records requests for something—anything—that might pull loose a thread to aid in some post-conviction appeal, no matter how unlikely. Sometimes, it’s just about hope. Wilson says there’s more to it in his case: He says he never would have been convicted if the jury had heard that tape. How he can be so sure is unclear, because he hasn’t heard it, either. Prosecutors, no doubt, would point out that a Roberson confession alone hardly exonerates Wilson. They never argued Wilson was the triggerman, but the getaway driver. The police memo saying Roberson confessed doesn’t refute any of this.

For now, though, Wilson isn’t asking anyone to believe him. He just wants the tape so he can prove what he’s saying. And his argument is pretty straightforward: If he’s going to be sentenced to almost half a century in prison for a crime, then surely he deserves a chance to listen to the recorded confession the government had in its possession. So far, he cannot.

Wilson is an able jailhouse lawyer. When MPD rejected his initial request, he appealed to Mayor Muriel Bowser’s office, later arguing that if MPD really didn’t have the confession, then it violated D.C. law requiring the preservation of evidence in murder cases.

“The June 14, 1999 audio recording was a case solving piece of evidence in a double homicide committed within the jurisdiction of the District of Columbia,” Wilson wrote in his appeal letter. “It is simply not reasonable to accept the assertion that someone in the agency just ‘surrendered’ this evidence to someone outside the agency. It is not merely unbelievable, it is unlawful.”

After receiving Wilson’s appeal, the mayor’s office told MPD to search its files. He scored a similar—if fleeting—win with the U.S. Attorney’s Office for the District of Columbia in an open-records request to federal prosecutors. Initially, federal prosecutors refused to confirm or deny the existence of the tape. After Wilson filed a lawsuit from prison, a judge ordered the U.S. Attorney’s Office to search for it. So far, neither agency has found any recording. After all, the FOIA law requires only that agencies conduct “an adequate search.”

Still, Wilson’s persistent efforts to pry loose the recording have created a paper trail of responses, denials, and appeals that raise questions about evidence handling, records preservation, and the public’s right to access records under the Freedom of Information Act.

So far, these records make clear, a murder confession has gone missing.

And nobody will explain why.

Around 2 a.m. on Aug. 17, 1998, with five bullets in or through him, Ronnie “Squid” Middleton managed to drive from the 1500 block of Congress Place SE about a mile up Alabama Avenue SE. He probably knew enough to fear his life would end this way. And then it did. And after years of piling up bodies, when it finally was his turn, Middleton drove himself not to D.C. General (which, in the summer of 1998, was still a hospital) but to the Seventh District MPD headquarters. Perhaps he wanted to say something about who did this to him, but when he finally arrived, he had little to say.

The white Ford Bronco barreled up to the front door of the station. As officers ran outside with their guns aimed at the Bronco, one spotted bullet holes in the driver’s side door. “He’s shot!” someone yelled. Officer James Craig tried to get Middleton to talk while paramedics were called.

“He did not respond to questions I asked and he appeared to be fading in and out of consciousness and he also appeared to be having trouble breathing,” Craig later wrote in a statement, though a detective later testified Middleton managed to say where the shootings had happened. Another officer remembered discovering Bradley in the backseat, moaning. She had been shot, too. According to prosecutors, a third person was in the car that night and managed to escape through a window.

Within hours, Middleton and Bradley would be dead.

Tommy Edelin was the first person charged in the Middleton and Bradley murders, though the killings were hardly the only crimes alleged. A massive federal conspiracy case charged Edelin with leading the 1-5 Mob drug gang. Prosecutors at the time said the organization sold hundreds of kilos of crack in Southeast throughout the 1990s and was responsible for at least a dozen murders, including those of a 14-year-old girl and her 20-year-old brother. They were shot and killed in a case of mistaken identity on the way home from a church Christmas party, though Edelin was acquitted in those killings.

The government’s theory in the 2001 trial was that Edelin was worried whether Middleton—his most trusted and efficient hitman—might turn and cooperate with the government. In the summer of 1998, Edelin and just about everyone facing charges in the case was locked up, but Middleton was still free—and on heroin. Prosecutors said Edelin feared that as soon as Middleton got locked up and started going through heroin withdrawal, he’d stand little chance of resisting efforts to get him to cooperate.

“And Tommy feared that although [Middleton] was a friend, it was just too big of a chance. So Tommy reaches out, and being the smart, manipulative guy that he is, he reaches out to an unlikely ally,” a prosecutor explained to jurors. That ally, according to prosecutors, was the Congress Park Crew.

A government witness testified that Edelin confided how, from jail, he reached out to the rival gang to have three men—identified in transcripts as “LT,” “Das,” and “Cool Wop”—kill Middleton and Bradley. But while Edelin was convicted in four murders and a host of other felony charges, then sentenced to life in prison, he was acquitted in the Middleton and Bradley murders.

Years later, prosecutors put forward another theory: Middleton was killed not to protect Edelin but to get back at him. Wilson wanted revenge, they said, after Middleton killed a close friend named Maurice Doleman. The killing triggered a bloody war between Edelin’s 1-5 Mob and the Congress Park Crew, according to prosecutors, who said Wilson drove the getaway car for his two purported accomplices—Draine and Roberson—both dead by the time Wilson went to trial in 2007.

Unlike in the Edelin case, however, jurors rejected conspiracy and racketeering charges. “Conspiracy? A crew? With the evidence the prosecutor presented, not one among us could see it,” one juror, Jim Caron, wrote to the sentencing judge after learning that some defendants faced decades in prison despite only being convicted of minor drug transactions (read more here). Caron died of a heart ailment a few weeks after writing the letter in 2008.

Prosecutors had better luck against Wilson. He was convicted of aiding and abetting in the Middleton and Bradley murders. He was sentenced to more than 45 years in prison. There were no eyewitnesses tying Wilson to the murders, the defense argued, but several witnesses testified against him, including Bobby Capies, whom Wilson and his lawyers believe is the undercover informant who elicited the confession from Roberson. On the stand, Capies told jurors that Wilson confessed to him.

“He was telling me that it was him [Wilson], [Draine], and [Roberson], said they was riding around smoking,” Capies told the jury. “And they rode through there and they seen [Middleton] in a truck, looked like he was smoking.”

“They went back around the block to get a gun. They pull up, and I guess they was going to a conclusion of whoever who was going to get out. [Wilson] said, ‘There ain’t no time for this, man. Y’all idling.’ So [Roberson] was like, ‘Man, it’s my gun, I’m going to do it.’”

But defense lawyers argued that just about everyone in Congress Park seemed to confess to Capies. They called him a liar willing to say whatever he had to say to work his way out of his own felony murder and drug charges. And they pointed to testimony in which he admitted to once lying to law enforcement.

Eleven years after the murders and nearly three years after Wilson’s conviction, his defense produced an affidavit from a D.C. Jail inmate who came forward to say that he, not Wilson, was the driver. According to the inmate, Roberson forced him at gunpoint to drive the getaway car. But Judge Richard Roberts ruled the confession wasn’t credible, in part, because Wilson and the inmate knew each other at the D.C. Jail. With the confession coming 11 years after the killings and more than a year and a half after the jury’s verdict, Roberts said the confession suggested “a last ditch effort for the defendant to escape punishment.”

In another post-trial motion, Wilson’s defense alleged “repeated and profound Brady violations” by the government—a reference to the Supreme Court ruling Brady v. Maryland that requires prosecutors turn over government evidence favorable to a defendant.

Among the pieces of evidence related to the alleged Brady violations is the MPD memo mentioning Roberson’s confession. Wilson’s attorney said in court papers that the defense only learned of the memo after the trial ended. But Roberts sided with prosecutors against a new trial, ruling the memo “was not exculpatory in any respect” because prosecutors had argued all along Wilson was the getaway driver and Roberson the shooter. And so a memo disclosing that Roberson confessed doesn’t contradict the government’s case, he ruled.

The assignment to search MPD’s files earlier this year for a copy of the recording fell to Detective Daniel Whalen, who said in a sworn statement that he had located a document in the Middleton and Bradley file describing how “an admission of involvement by a suspect was covertly recorded via the use of wired cooperating informant.”

But Whalen said he couldn’t find the actual recording.

He said MPD appeared to have surrendered it to the Bureau of Alcohol Tobacco and Firearms but never got it back. The detective also found a handwritten note in the files saying that a transcript of the recording was supposed to be made available. But “there is no documentation in the homicide file to show that a copy of this transcript was ever actually received by the MPD,” Whalen said.

According to Whalen, the tape wasn’t anywhere else in the homicide files, either. And, according to MPD, that was good enough because the agency had conducted an “adequate search” under the open records law. The case was closed.

In an appeals letter to the mayor’s office, Wilson argued that surrendering the evidence without retaining a copy violated D.C. law that requires the preservation of evidence in murder cases. He also said there’s no indication MPD tried to contact ATF or the retired police detective who worked on the Middleton and Bradley homicides.

The mayor’s office referred Wilson to the D.C. Office of Inspector General if he wanted to request an investigation into whether evidence rules were broken, but sided with MPD and rejected his appeal.

City Paper sent a detailed list of questions to MPD about whether the agency made a copy of the recording prior to surrendering it to ATF, whether MPD looked outside of its own homicide files, and whether surrendering copies of a murder confession squared with MPD chain-of-custody rules.

After two weeks, MPD spokeswoman Gwendolyn Crump wrote, “We are declining to comment. Please direct your questions to the U.S. Attorney’s Office.”

In 2013, Wilson filed a similar but slightly different FOIA request with the U.S. Attorney’s Office, this time naming Bobby Capies as the undercover informant who spoke to Roberson. Initially, the department declined to confirm or deny whether the record existed, citing privacy and other exemptions under the FOIA law. Acting as his own attorney, Wilson sued. In a pretrial ruling, U.S. District Court Judge James Boasberg sided with the inmate.

“The existence of the tape is not a matter of mere speculation,” Boasberg ruled, rejecting the U.S. Attorney’s Office initial motion to dismiss the case. “Rather, two documents disclosed in the wake of Wilson’s trial indicate that such a record is likely to have been created.”

Boasberg ordered the U.S. Attorney’s Office to search its files. In the 160 boxes of records on the Congress Park Crew prosecution, officials located one document titled “running resume,” according to court records. “It is an account of the conversation that Mr. Wilson is seeking,” U.S. Attorney’s Office FOIA liaison Karin Kelly stated in a sworn declaration in which she outlined her search for the recording.

“It is also the only document I came across that made any mention of Bobby Capies wearing a body recording device and speaking with Antonio Roberson,” she stated. “I did not find an actual recording of the conversation, nor did I find a transcript of the conversation.”

Kelly later emailed one of the assistant U.S. attorneys who prosecuted the Congress Park case for ideas on where the recording might be, but she never heard back, according to court records. Still, the U.S. Attorney’s Office filed a motion to dismiss Wilson’s case because it had conducted “an adequate search” for the recording, meeting its obligations under the FOIA law.

And, government attorneys added in another declaration, all documents responsive to Wilson’s request would have been located at the U.S. Attorney’s Office, because there were no other systems of records across the Justice Department—which includes the ATF—where Wilson’s case would have been maintained. Boasberg agreed with prosecutors that an adequate search was conducted. He tossed the case.

None of this explains where the recording is and why Wilson can’t obtain a copy. Whether you think he’s guilty or not, or whether the tape helps or hurts his post-conviction efforts, Wilson says he deserves to listen to it. And if there’s any chance, however small, the recording could exonerate Wilson, is “adequate search” under the FOIA law enough?

In response to questions about the location of the recording, including whether anyone sought to contact ATF to locate a copy in response to Wilson’s FOIA, a spokesman for the U.S. Attorney’s Office declined to discuss specifics regarding Wilson’s case.

“The U.S. Attorney’s Office takes its constitutional and ethical obligations very seriously,” spokesman Bill Miller wrote in an email.

“We rely on expansive policies, frequent training, and robust checks and balances to ensure that we not only meet—but exceed—our constitutional and ethical obligations. Although Mr. Wilson’s FOIA lawsuit has been dismissed, his appeal in the criminal case remains pending before the United States Court of Appeals for the D.C. Circuit. For that reason, the U.S. Attorney’s Office has no comment about this particular matter at this time.”

Wilson said his efforts to find the tape continue, despite setbacks with MPD and federal prosecutors. While the U.S. Attorney’s Office said records in Wilson’s case are unlikely to be anywhere else within the Justice Department, he’s filed a FOIA request with ATF. He’s also preparing to file a complaint with the D.C. Office of Inspector General, as well as a lawsuit against the District.

But on July 28, the U.S. Court of Appeals for the D.C. Circuit upheld Wilson’s conviction in a 2-1 vote. “Even considering the cumulative effect of the multiple alleged Brady violations,” the majority wrote, “the untimely or suppressed materials are insufficient to undermine our confidence in the jury’s verdict.”

Dissenting, Circuit Judge Robert L. Wilkins argued that Wilson deserved a new trial. He didn’t rule on the Brady violation allegations, but said Wilson’s defense was ineffective because his lead attorney became ill and the replacement attorney had missed crucial parts of the trial.

In the hundreds of pages of post-conviction motions and appeals court filings, however, the memo on the undercover recording is barely mentioned. It was a footnote in Robert’s ruling, and it wasn’t mentioned in the appeals court decision.

But Wilson says a memo saying a confession took place is altogether different from hearing the confession itself. With the courts paying scant attention to the question of whether the tape could clear him, Wilson said he’s relying on the Freedom of Information Act to find out.

Stephen Saltzburg, a law professor at George Washington University who served as a deputy assistant attorney general in the Justice Department’s criminal division, said the inability of any agencies to locate the tape was “troubling in connection with a murder investigation, which is certainly the highest priority crime.”

“You’d think that if Wilson was mentioned on the tape, the government would have let that be known,” Saltzburg said. “I think it underscores the legitimacy of asking what happened to this tape.”

American University professor Jon Gould, head of the Preventing Wrongful Convictions Project, said one of three things could’ve happened to the tape.

“It’s highly unlikely that it’s the one that Wilson wants to argue, which is that it’s a giant conspiracy between the U.S. Attorney’s Office and MPD because they know it’s exonerating and they destroyed it. Is it possible? Yes. Is it likely? Not with this U.S. Attorney’s Office and probably not with this MPD. The D.C. criminal justice system is generally much better than other places in the U.S., so I would be quite surprised if they were intentionally destroying exonerating evidence.”

The second possibility is that “the evidence in the case just got put out to pasture because they basically clean house on a regular basis, and it’s an old case at this point,” he said.

The third, and most likely, Gould said, was that “it got lost somewhere.”

“We see communication between prosecutors and police departments sometimes have difficulty with each side knowing where key evidence has been kept.”

Still, the fact that the tape has not been located does raise questions about evidence control, Gould said. But for Wilson to prove a legal violation, he needs to be able to argue why he thinks the tape will exonerate him, Gould said.

“Regardless of whether there’s a legal violation, it’s an embarrassment to the MPD and to the U.S. Attorney’s Office, and I can imagine a judge saying, ‘I want to get to the bottom of this. A confession in a murder case is something I want to know more about and why it is you don’t have the confession?’”

Asked why he’s so sure the tape will exonerate him, Wilson said he recalls walking up on a conversation between Roberson and Capies around the time when the police memo said the confession took place. He said he only caught the end of the conversation, but Roberson had been drinking, and he was telling Capies that he drove himself and killed Middleton in retaliation for the killing of a friend.

At this point, Wilson has little to lose by lying. Credible or not, he says he is not asking to be believed—he’s just asking for the tape because he deserves to listens to it. He insists that once he has it, though, he’ll be cleared.

It’s a confession David Wilson may spend decades wondering if he can ever hear.