The Josh Black Case: Even After His Unexpected Release from a Life Sentence in Prison, He Continues to Harbor Questions About His Troubling Jackson Hole Case

By Alec Klein

Special to the Wyoming Truth

DANA POINT, California—Over five years have passed since Josh Black somehow walked out of prison from what was supposed to be a lifetime sentence without the possibility of parole. So much has happened since then: Teton County agreed to pay Josh $135,000 after the Wyoming Supreme Court excoriated the prosecutor for misconduct that deprived Josh of a fair trial. And the Wyoming Supreme Court suspended the prosecutor for three years, so gross were the misdeeds.

And yet.

If all of that served as a prelude to vindication for Josh, it’s hard to tell. That’s because, after serving nearly six years in prison, Josh can’t help but wonder what really happened in his aggravated assault case. He retraces his steps. He deconstructs the days leading up to his shackling by sheriff’s deputies on Oct. 26, 2014, when his life was radically upended.

Among the unanswered questions: What should he have made of his then-girlfriend’s speeding ticket? Why was the sheriff deputy’s business card in her car? And what should have been made of the suitcase of marijuana found in her closet on the day of Josh’s arrest?

“What really happened that night?” Josh, now 45 years old, asked rhetorically in a recent interview with the Wyoming Truth. “I’ll never know.”

Though much has been covered in the press about his high-profile case, a strange and troubling tale, what is laid out here in the Wyoming Truthhas not come to light before now. The following account is largely based on unearthed records, voluminous documents, including sheriff’s reports, DNA records, blood tests and on exclusive interviews with Josh and others connected to the case.

This is what Josh said happened in the beginning: He was in love. He had met his girlfriend on Tinder, the online dating app. They had seen each other for a couple of months before she moved from southern California, where they lived, to Jackson, Wyoming. It was the fall of 2014 when she called him from Wyoming. “You’ll never believe what happened to me,” she told him.

The day before, she had been pulled over for speeding by Sheriff’s Deputy Andrew Roundy of the Teton County Sheriff’s Office. Court records confirm Roundy’s citation of her for “superintendent speed zone” on Sept. 3, 2014. Josh didn’t make anything of the event—not then.

Soon after that, she urged Josh to move in with her. Josh was surprised as she had resisted his entreaties to move from southern California, where he was working as an account manager for a marketing firm, to be with her in Jackson, where she was a horse trainer.

Now, though, circumstances had changed. “She asked me to bring pot from California,” Josh said.

And not merely a trivial amount. Josh said he transported marijuana—over a pound—in a box about the size of a beach ball, which he has since admitted to authorities. His girlfriend’s idea, he said, was for them to deal the marijuana, which is illegal in Wyoming, and make some side cash. His then girlfriend couldn’t be reached for comment.

On Oct. 19, 2014—day 1—he arrived at her apartment resting on a slope in Teton Village, and the trouble was about to begin.

The business card

Day 2. October 2014. Josh was with his girlfriend in her car when a bump in the road jostled the sunglass holder above, flipping it open, and a business card fell out. Josh took a hard look at it and couldn’t quite comprehend what he saw: the name of Officer Roundy.

“Why do you have a cop’s card when you have a pound of weed in the closet?” Josh asked her.

She reminded Josh that she had been pulled over weeks earlier by Officer Roundy. 

Day 6. Oct. 26, 2014, a Sunday. Josh and his girlfriend awoke, after which she smoked marijuana before heading off to church, according to sheriff’s records. They grabbed breakfast at the Virginian, a popular café in Jackson, where they also drank Bloody Marys and Mimosas. It was a mild day by Wyoming standards—Josh was wearing a T-shirt, though it would snow later that day—the first of the year. There was no indication of what was to come.

It seemed like a cozy, desultory day between a couple in the early blush of a relationship. Throughout the day, Josh said, there was drinking and pot smoking and the quotidian matters of life, including grocery shopping. At one point, they found themselves at a cul-de-sac, playing in the snow, records indicate.

At about 9 p.m., after they arrived at her apartment, Josh went to sleep; he would have to wake up early for his construction job the next morning. Or so he thought. But at about midnight, Josh said he was awoken by a cold breeze. As he sat up, he realized that the balcony doors of the bedroom had been flung open to the outdoors, and his girlfriend was silently tossing his clothing out over the balcony and through the front door.

“What the f— are you doing?” he asked as he got up.

She didn’t answer, instead running to the living room couch and covering her head with a blanket.

Josh didn’t say it then but this was one too many things; he was done with the relationship. This, he thought, wasn’t what he signed up for. There had been a similar incident a few nights earlier, when he said his then-girlfriend had awoken him, ranting for no apparent reason. Now, again. Josh put his discarded clothing away and went back to bed, resolving to quit his job and head back to California in the morning.

“What happened?”

At about 5 a.m. that morning, Josh said he was awoken again—this time by the sound of his girlfriend crying in the bathroom. He got out of bed and turned on a light in the bathroom. That’s when he said he saw it for the first time: There was a cut on her forehead. Her eyes were swollen. She had been beaten badly around her face and neck, records show. He wiped the blood from her forehead with his T-shirt.

“Babe, what happened?” he said he asked. “Where were you?”

She kept sobbing. He said he panicked; after all, he had had some run-ins with the law back when he lived in California. He didn’t trust the police. He didn’t know what to do. He insisted that he take her to the hospital. She wouldn’t have it. Instead, sheriff’s records show, they went back to bed together.

At no time during this period did she call 911, records show. “She said she doesn’t know why she didn’t call 9-1-1 then,” sheriff’s records stated, adding, she also “doesn’t think she ever tried to leave and doesn’t know why.”

For a time, Josh lay awake uneasy—until about 7 a.m. when there was a knock at the door.

Precarious position

That morning, sheriff’s deputies arrived on the scene, including Officer Roundy. This was the same officer who had pulled over Josh’s then-girlfriend for speeding. This was the same officer whose business card showed up in her car.

Upon his arrival, Officer Roundy found Josh’s girlfriend in only a white bathrobe, sheriff records show. Roundy went into the bathroom with her and shut the door, Josh said. The extent of the conversation between her and the officer isn’t known. Officer Roundy’s recorder stopped recording. “I started to record my contact with [Josh’s girlfriend] with my pocket audio recorder. For an unknown reason my recorder stopped recording shortly after six (6) minutes,” Roundy wrote in his sheriff’s report.

Josh said they were in the bathroom for about 20 minutes.

Only much later, after being handcuffed and taken to jail, would Josh begin to piece together some of the fragments of his last hours of freedom.

That last night, his girlfriend had taken two Ambien sleeping pills, according to Teton County Sheriff’s records; later, he would research the side effects, exacerbated by drug and alcohol use, which could include hallucinations and aggression.

Later, he would also learn that she had taken a cell phone photo of her battered face a little after 10 that night. At about 2 a.m., she sent that photo to a friend, accusing Josh of beating her. The friend called 911, which explained how authorities turned up to arrest Josh that morning.

Some things didn’t add up. For one, the DNA found under Josh’s girlfriend’s fingernails—a sign of a possible violent conflict—were not Josh’s but that of an “unknown contributor,” according to the sheriff’s report of DNA testing.

What’s more, his girlfriend’s blood was discovered on the steering wheel of her tan Mazda Tribute, according to the sheriff’s report of DNA testing, indicating that she had left the apartment at some point that night. At what point, then, did she return home, getting back in bed with Josh the following morning?

What’s more, sheriff’s records show that she told authorities that there were “two containers filled with Marijuana in the closet, under the hanging clothing, in a suitcase belonging to BLACK … she was going to introduce him to the person she gets her marijuana from.”

What happened to the marijuana? Why wasn’t Josh or his girlfriend charged in connection with it? And, Josh would later wonder, to what extent was his girlfriend being cultivated as a confidential informant for law enforcement?

Authorities didn’t want to charge his girlfriend with drug-related offenses because it would have weakened their case against Josh, the records indicate. According to a 2016 letter from the Office of the Wyoming State Public Defender to Josh, Tina N. Olson, the chief appellate counsel wrote, “It seems [Josh’s then-girlfriend] was not a CI [Confidential Informant] but was being developed as one because of the amount of drugs found in the house at the time of the incident. All drug charges were dropped at the police level because they would have had to charge [Josh’s then-girlfriend] also. Det. Roundy explained they did not want to damage [her] presentation as a victim by charging her in drug crimes because she was so beat up and drug charges may severely hinder their assault case against you.”

This raised all sorts of questions, not the least of which was whether one crime was okay to overlook in the pursuit of the prosecution of another crime. But there were other questions, too. Why was his girlfriend being cultivated as a confidential informant in Jackson Hole, a comfy place where oftentimes the worst crime was a driving infraction or a fishing license violation? And what should have been made of the coincidence that the same sheriff’s deputy who flagged his girlfriend for speeding was the same sheriff’s deputy who turned up on the morning of his arrest? And what were the chances that the sheriff’s deputy’s recorder would suddenly stop working when he was shut in the bathroom with that same confidential information in the making?

The Teton County Sheriff’s Office, Roundy and Josh’s ex-girlfriend did not respond to requests for comment. Olson, who now works as a public defender in the Michigan State Appellate Defender Office, said in an interview for this story that she did not have “a clear recollection” of the confidential informant issue as it had occurred several years earlier.

But Olson, who drafted the appellate brief that led the Wyoming Supreme Court to give Josh a new trial, also said, “I thought it was very appropriate that a new trial was ordered for Josh because of how his case was prosecuted. That was the correct outcome for him.”

Weeks after the incident, records show that Josh’s girlfriend texted a friend about the night in question, saying, “Then the first pics of my face were at 10:30 so somewhere in that hour something happened which I honestly can’t recall.”

All that Josh knew when sheriff’s deputies showed up the following morning was that he was in big trouble. He had already been convicted of multiple felonies in California. One was for a DUI, records show. Another involved an altercation with someone trying to repossess his car, he said, while the third occurred when he got in an argument with his roommate, he was locked out of their apartment and he kicked in the door. Both people involved in these run-ins with Josh said they were willing to testify on Josh’s behalf that he wasn’t a violent person, according to Todd Bontecou, who had been hired as a private investigator during Josh’s appeal.

Altogether, those prior incidents placed Josh in a precarious position in Wyoming—as a habitual offender. As Josh was arrested and removed from his girlfriend’s apartment, sheriff’s records show, “she shouted to him that she was sorry.” 

Once he was convicted in 2015 by a jury of the aggravated assault and battery of his then girlfriend, he was automatically sentenced to life in prison.

Josh was 35 years old.

Prosecutorial misconduct

Over the next several years, Josh taught himself the law in a maximum-security prison. The tutelage was spartan; he had no internet access behind bars but he did have walled-off access to case law. Armed with that legal knowledge, Josh began to file his own briefs and direct appeal, arguing that he was the victim of prosecutorial misconduct.

Meanwhile, Bontecou, the private investigator, spent years investigating the case. For Bontecou, the first real red flag was what he saw—or didn’t see—when he went to take a close look at the apartment where the alleged incident occurred. He said there was no blood spatter at all on the sheet rock white walls, which was “inconsistent with her account” of being repeatedly beaten and slammed against the walls. “Where’s the blood?” Bontecou asked. “How could a beating that severe have happened in that apartment? It’s simply implausible.”

The Wyoming Supreme Court ultimately awarded Black a new trial, citing several problems with the case, including the prosecutor’s failure to comply with a judge’s order to produce cell phone and Facebook records. The prosecutor told the judge he sought and couldn’t obtain the records but the prosecutor did not seek to obtain those records. That stunning fact raises at least one big question, at least for Josh: Was there something to hide in those records? Was that why the prosecutor simply ignored the judge’s order and failed to seek to get those records? Even further, could it have had anything to do with his girlfriend being developed as a confidential informant? Josh believes those records, had they been obtained as they were supposed to, would have proved he wasn’t with his then-girlfriend when she was hurt that night. But those records were no longer preserved by the time of Josh’s appeal. The Wyoming Supreme Court also found the prosecutor committed misconduct in his opening remarks and closing statement.

“The prosecutor’s failure to comply with the court’s discovery order is not the only instance of misconduct relevant to our decision,” the Wyoming Supreme Court justices wrote.

As a result, the Teton County prosecutors offered Josh a plea deal—willing to give him $135,000 and his freedom—which he took rather than risk the gamble of another costly trial. Then a disciplinary hearing by the Wyoming State Bar found the prosecutor, Becket Hinckley, violated seven rules of professional conduct and recommended to the Wyoming Supreme Court that he be stripped of his law license. Hinckley did not respond to a request for comment. Richard D. Stout, the Teton County and prosecuting attorney, said, “Mr. Black’s case predates my tenure with this office. None of the prosecutors that worked on Mr. Black’s case are currently working in this office. Accordingly, I have no comment on the matter.”

Honorable burden

Josh served about five and a half years in prison until he was released in March 2020. For a time, he worked in Cheyenne as an electrician at a Microsoft data center. He was living in Casper, Wyoming.

The plan, though, was always to return to California, where he was born and raised. Back to the ocean and the waves that beckoned him to his past that also signified his future.

Today, he lives in Dana Point, a beautiful oceanside resort town—almost, it seems, the opposite of an enclosed, sterile prison. He’s working as an electrical technician, specializing in solar and other renewable power plants. He lives near the ocean. When he has time, he surfs. He rides one of his three Harley Davidsons. And he works a lot. The dream, for him, is to be free enough that he doesn’t have to work. To start a family one day. To surf more.  

But a part of him—a big part—is entrenched in the here and now.  “I’m not glad for the stuff that happened,” he said, “but I’m grateful for what it made me today.”

He lives with the hauntings of what happened and sent him to prison. There was a time, he admits, when he wanted to kill himself. When he eats, he doesn’t use a knife—because a knife wasn’t available in prison and that’s what you get used to. The limitations, the confinement. Inside prison, you get used to cutting your food with a plastic fork.

But Josh is purposefully driven. Josh hears from prisoners, watchdog organizations and legislators from various states, who want his help and hard-earned wisdom: How did you do it? By “it,” they mean, how did he beat the system, overcome a lifetime conviction and regain his freedom?

The answer, he said, is: “You can never give up.”

Josh also hears from various advocacy groups that seek to glean insight from his own harrowing experience. Josh welcomes this role, even though it’s a position that he never sought—that of one who can now help others with injustices.

“I call it,” he said, “my honorable burden.”