would be seventeen and fourteen by the time his case rolled through a federal courtroom in Harrisonburg, Virginia, the following year. Judge Michael Urbanski would approve a plea deal negotiated after a series of meetings between Wolthuis and Santiago’s lawyer—who, incidentally, had been at the Southern District of New York courthouse in Manhattan waiting for him on the day of his arrest. “The elevators opened, and there was his lawyer; he’d already beaten us there,” Metcalf said, believing the quick legal service signified high-level cartel connections.
Wolthuis wasn’t so sure, saying that the E-word—evidence—just wasn’t there. “If Santiago was truly Mr. Big, why would he be selling to a couple of wahoos in a small Virginia town?”
Santiago had tried to find work when he got out of prison, picking up odd jobs, his attorney wrote in his presentence memorandum. But finding legitimate employment is exceedingly hard for felons, and the odd-job income wasn’t enough to provide for his family, so “against his better judgment [he] drifted back into criminal activity,” his attorney noted. “He deeply regrets his actions, and is aware of the strict penalty he is about to face. He has let down his children and feels a great sense of guilt and shame for his actions.” His father was murdered when he was four months old, and Santiago, a high school dropout, grew up mired in poverty, the report said. In his late twenties, he ran a small party- and event-planning company, called Self-Made, and worked freelance as a music-video stylist.
Compared with Jones, who received a twenty-three-year prison sentence, and Shaw, whose cooperation earned him the lesser sentence of eighteen years, Santiago was merely a “flipper,” as Wolthuis described him, not part of the on-the-ground heroin distribution ring. He pleaded guilty to distributing between three and ten kilos of heroin, which equates to an average of sixty-five thousand shots of the drug, and was sentenced to ten years in federal prison.
On the day of his sentencing, Metcalf personally transported him to a federal courthouse in Charlottesville. On the way, Santiago tried to taunt him. He wanted to know if Metcalf had heard about the recent slaying of two New York Police Department officers. They’d been ambushed by a Baltimore man who bragged on Instagram that he was “putting wings on pigs.” Metcalf nodded.
“Metcalf, you really think you’re doing something, don’t you?” Santiago said. “But you ain’t changing nothing. This shit ain’t going away.”
“Man, I’m just doing my job,” Metcalf said.
“Helluva thing to take a man away from his family,” Santiago said.
“Yes, it is,” Metcalf agreed.
Santiago reminded him one more time: There were people out there who were not afraid to put wings on pigs.
*
Jones and Santiago were right, of course. Shit did not stop. That’s not the way addiction works. That’s not typically how prison reentry plays out. It didn’t stop when Dennis Painter’s father moved heaven and earth to get him into treatment again in the wake of Jesse Bolstridge’s death—only to have him continually push through the revolving door of rehab, relapse, and jail.
Naming his new baby after Jesse as a reminder didn’t stop Dennis’s behavior either. Nor did the abstinence-only Nashville treatment center his dad sent him to, his seventh attempt to get clean. “I’ve never gone through the stages of grief about Jesse,” Dennis told me. He said he’d tried to kill himself “like six times, but it just didn’t work. I’ve just been getting high since it happened.”
When the Jones/Shaw ring came to a close, Dennis and his friends simply got back on the heroin highway to Baltimore—although in nearby Winchester he could now buy it for $20 a bag, compared with $30 when bought from a runner in Woodstock.
I told Dennis that Jesse’s mom, Kristi, really needed to know what happened the morning that Jesse died. “She wants me to vividly describe what I saw when I walked into the bathroom, but she doesn’t need that image in her head,” Dennis said. He added that he used to go to Jesse’s grave but stopped because it was just too hard. “I have a lot of guilt about it. I want to write a letter, get some things off my chest. It feels like if I’d never gone to get the dope that day, he’d still be alive today.” Dennis used to spend Thanksgiving at Jesse’s house. He, too, had preschool pictures of them at Grasshopper Green.
Dennis described the problem exactly as Metcalf had: If OxyContin had been the economic driver in the Appalachian