
John Jay Roach was serving a 14-year sentence at Richard J. Donovan Correctional Facility in San Diego when he felt a knot in his gut that wouldn’t go away. “Bellyaches, bellyaches, bellyaches,” he later recalled. According to Roach, he went to the doctor, who said he was fine. Roach disagreed and kept returning for exams, eventually filing an appeal for more thorough testing. The following spring, a CAT scan confirmed late-stage liver cancer. “They looked at it and said, ‘Oops.’”
On August 16, 2018, at the age of 61, Roach was transferred to the hospice unit at the California Medical Facility, a prison in Vacaville where doctors and nurses are on hand to provide chronic care for more than 2,300 inmates, including terminally ill patients in hospice. (California Correctional Health Care Services, which oversees prison health care in the state, declined to comment on Roach’s account, citing patient-privacy laws.) During intake, Chaplain Keith Knauf interviewed Roach about his family and spiritual life. Part of Knauf’s job is to track down family members, old friends, and victims so that patients can seek forgiveness, if they wish. “These men have burned a lot of bridges,” he said. Roach told him his mother had passed away years before. Two younger sisters, Denise and Dawn Marie, now in their 50s, had heard enough apologies to last a lifetime, but Knauf tried to reach both of them. He managed to get through to Denise, but she refused to be put on the phone with her brother. The chaplain passed along the message that Roach wanted to apologize again.
Beginning in 2010, the U.S. prison population began to fall for the first time in decades—yet the number of older inmates has nearly tripled since 1999. Inconsistent data and accounting make health-care costs difficult to track across all 50 states, but one trend is evident: As the average age of prisoners has risen, so too has the cost of caring for them. The isolation and stress of prison life accelerate the aging process, and a lack of quality medical care can lead to health problems that could be managed with ease on the outside. By some estimates, incarcerating older inmates costs anywhere from three to nine times more than younger prisoners—largely due to health-care costs as prisoners age.

The Gift of Love is a 10-bed hospice in a residential neighborhood off Highway 1 in Pacifica, where the cliffs drop to the sea. There the sisters of the Missionaries of Charity live a contemplative life inspired by their founder, Saint Teresa of Calcutta. They spend about six hours in prayer six days a week, and nearly every waking hour on Thursdays.
By the time I meet Roach, he is just weeks away from death. The sisters provide interviews about their work only on background, preferring to avoid media attention, but they grant me permission to visit Roach so long as he’s comfortable talking. What I want is to spend time with one of the rare inmates granted compassionate release to learn what freedom means to someone who is dying—and to understand what matters most to him in his final days. We speak at his bedside between his doses of morphine, tracing the contours of his life when his mind is clear. To fill in the details, I speak with his friends, lawyers, and caretakers, and follow a trail of papers documenting a life entangled in the criminal-justice system.
The first time I visit, in January 2019, I find Roach resting in room two, across from the medicine room. His adjustable hospital bed sits beneath a crucified Jesus, and a window lets in a trapezoid of sun from the patio. Eight months after his diagnosis, he still fills out his dark sweatpants, gray shirt, and black ski cap, but the tattoos on his wrists and chest look as if they are melting into his jaundiced skin. On a bedside table is a smoothie and a bell to ring if he needs one of the sisters.
I ask how they knew he’d atoned. When he doesn’t respond, I ask if he thinks he’s atoned.
“No,” he says. “Not really.”
The sisters got in touch with Denise and Dawn Marie, but they said they didn’t want to be contacted again, not even when their brother died. One of the volunteers found Roach’s sisters on Facebook and showed him their pages. “There was a picture of my mother on there,” he says. “It was a nice picture. I’d like to get that picture.” When Roach drifts off to sleep, I take out my phone and pull up his sister’s account. When he comes to, I show him a picture I found of his mother. “That’s her,” he says, coughing. “She was a good-looking woman.”
One reason compassionate release isn’t as effective as advocates want it to be is because it can be difficult to prove that a person fulfills its requirements, and the requirements themselves are idiosyncratic. In California, for example, patients require a prognosis of six months to live to qualify for compassionate release, yet predicting how long a patient has to live is one of the most difficult things for a doctor to do. “A prognosis doesn’t mean I guarantee he’s dead in six months,” DiTomas said. “It means there’s a greater than 50 percent chance that you will not be alive in six months.” She and other experts argue that the prognosis requirement should be extended to one year to give doctors a more realistic time horizon for determining whether patients are eligible.
On February 8, I’m at Roach’s bedside again. His head is sunk in the pillow, eyes closed, hands folded as if in prayer. One of the sisters has hung the picture of his mother above the window.
Dying can bring two bodies together. And so it is Taylor who has been sitting with Roach, who talks even when his friend is too far gone to listen. Taylor looks even better than the last time I saw him, sporting a camouflage jacket and a baseball cap. He’s just received a free smartphone from a public-assistance program, and he’s learning to use the touchscreen.
By the year 2030, one-third of U.S. inmates will be over the age of 50. In hopes of expanding compassionate release to meet the oncoming wave of ill and elderly inmates, criminal-justice advocates are pushing for reforms like clearer eligibility criteria, more realistic timelines, and more supportive release planning. Yet a lack of transparency about the programs makes it difficult for policy makers to take action, or even recognize the scale of the problem. Fewer than half of states with compassionate-release policies collect and track data on how many people apply for and receive compassionate release. The information I requested from the California Department of Corrections and Rehabilitation for this story is part of a new data-collection process that began just this year. Without meaningful records of the process, the stories of the men seeking compassionate release might well die with them.
The sisters stand and sing. Taylor, weak on his feet today, sits on a fourth chair, across from the empty ones. Roach wanted to be buried side by side with his wife, and now I wonder where she is buried and how she got there. Whether there was an empty chair for her husband at her funeral.
When Taylor’s voice fades out, there’s a charge in the air, like rain is coming. The deacon retreats to visit his wife, who is buried elsewhere on this hill. Taylor isn’t ready to go home. Just when everyone turns for their cars, another song overtakes him: “We are standing on holy ground, and I know there are angels all around …” He takes a deep breath for the next line, and his voice comes again, stronger now, as if from the good, clean lungs of a young man.