BJ Oct 1990

Bob Riley, a wandering-wondering Deadhead, enjoying a sunny day in New York’s Central Park, in 1990, after several Grateful Dead shows.

Update: Sentence not commuted. Bob Riley, a kind soul who “treads lightly in this world,” is in the 22nd year of a federal life without parole LSD sentence.  The details of his unjust sentence are summarized in this New York Times article.

This story is about Bob, the human being. It was written with Bob’s help, to reflect his unique voice.

“Humanity I have; it’s freedom that I lack.” — Bob Riley

“What point can there be in forcing a Deadhead to die in prison?”asks Bob.

 Bob says thanks for caring.

Bob was arrested in 1992 for mailing LSD and mushrooms to a fellow Deadhead in Iowa. He was sentenced to life without parole in 1993.

Prosecutors falsely labeled Bob as a career criminal because he’d used, shared and sold drugs over the years. He’d been arrested three times over 15 years for a puny amount of drugs.

His first arrest? Selling a joint on a San Diego beach. In all, his three arrests were for one-fourth of an ounce of pot, 3 grams of hash and $25 worth of amphetamines.

He fully admits he was selling (and using) mushrooms and LSD during his time on the road with the Grateful Dead and he understood the risk risk of getting locked up for a while. But life without parole in a federal penitentiary for a low-budget, gentle hippie wanderer who was utterly inconsequential to the drug trade or public safety? The idea seemed — make that, was and is — crazy.

Judge Ron-Longstaff

Bob’s judge wants sentence reduced

Robert’s arbitrary, senseless, unjust sentence illustrates why respect for the justice system is properly low today.

“The mandatory life sentence as applied to you is not just, it’s an unfair sentence,” said U.S. District Judge Robert Longstaff, a Reagan appointee, when he sentenced Bob. The judge had no choice because prosecutors had manipulated career criminal sentencing labels to generate a “mandatory minimum” of life without parole.

Bob was a victim of the government’s disgraceful campaign targeting of Deadheads because of their lifestyle.

In 2002, Judge Longstaff wrote President Bush, a fellow Republican, asking that Bob’s sentence be commuted. His plea for justice was ignored.


Robert Riley, Prisoner 59047-065, U.S. Penitentiary, P.O. Box 2099, Pollock, LA 71467

More than a decade later, Bob still lives in a cell at the high-security federal penitentiary in Pollock, La.

Traveling man
Bob and Red Rooster, his first new car

Bob and the Red Rooster, his first new car

Bob admits some shame about his inability to “settle down. There was always something messing me up, making it impossible to stay put.”

He found out through trial and error that he wasn’t hard-wired to live a conventional settled life.

He played for a 9-0 football team in junior high school in Wisconsin but gave it up in high school. Reason: he’d lost the urge for physical confrontation.

At age 18, he enlisted in the Army, only to be honorably discharged a year later. “I was not a killer of men.”

Bob didn't last in the Vietnam era Army. "I'm not a killer of men."

Bob didn’t last in the Vietnam era Army.

Bob got married at 24. He and his wife had two lovely kids, a daughter and a son.

To his everlasting regret, Bob failed that relationship. “My children’s mother is a beautiful person, but I seemed wired as a wanderer — a ‘Wonderer.'”

After his marriage’s disintegrated, Bob found happiness roaming the country, north to south, east to west.

The Deadhead years
Deadhead campground at Apple Valley in 1989.

Deadhead campground, Apple Valley, 1989.

During his travels, he found an extended family: the followers of the Grateful Dead. In Bob’s words, “People unafraid to be barefoot on the Earth.”

Among the shows that Bob never missed: Alpine Valley in East Troy, Wis.

Shows never missed: Alpine Valley in Wisconsin.

He considered himself part of the Core 5,000 of Deadheads, also called the Tour Heads because they followed the band on tour.

“This group demanded everything that a Fortune 500 company demands — honesty, timeliness, trustworthiness, integrity and, most importantly, they will uncover you if you fail to live up to those demands,” Bob says.

“It was never the drugs. It was the people — an honest, humble Tribe united together at hip and mind. I felt at home in this loving ‘simplicity,” he says.

For a supposedly important drug dealer, Bob lived on a shoestring,  traveling and camping, renting small apartments, staying with friends, owning almost nothing.

He survived doing odd jobs. He worked on a fishing boat in Alaska, an oil rig in the Gulf., skidding logs using teams of horses in northern Wisconsin.

“I wore many hats,” Bob says. “The members of one’s true family seldom grow beneath a single roof.”

“Hello, it’s Bob”
San Diego, 1981. Bob flies kites with sister Annie's boys.

San Diego, 1981. Bob flies kites with sister Annie’s boys, Chris and Nate, and her husband Bob.

His sister, Annie, remembers being in the Navy in San Diego when she’d get unexpected calls from her rambling brother. “Hi, I’m at the bus station. Wanna pick me up?”

Bob would stay for a few days, maybe a week, then move on. “He couldn’t be still, could not ‘settle.’ He was a free spirit, a modern vagabond,” Annie says.

Today, at 62, his musical tastes have changed and his philosophical ideas have deepened. He listens more to Rachmaninoff and Grieg than Jerry Garcia. He’s written volumes of poetry and studied all the great philosophers during two decades of reading in prison.

“I am never alone. The great poets, writers, philosophers… man’s greatest minds are counted here as friends,” he wrote in one letter.

Next of kin

Despite his optimistic nature, a sadness pervades Bob’s imprisoned soul.

He dearly misses his children, not having seen them since 1983. “I did not mean to be gone this long,” he says.

And he misses his younger sisters, Annie and Toni, and his late mother, with whom he was especially close. “Ours was a beautiful family,” he says. They miss Bob, too.

Bob’s future?

If released,  Bob would return to the town of his youth, Trent, S.D. His parents’ modest home is furnished but vacant, awaiting the return of the prodigal son.

Bob lived in Trent (pop. 232) until 1963, when he was 10. The family moved to Wisconsin for his father’s job. His parents returned home to Trent for retirement in 1987. Annie came back, too, after retiring from the Navy.

Bob’s father died in 2002, his mother in 2013. Bob missed the funerals.

Today, Bob’s home-in-waiting sits quiet, blanketed with snow. An easy chair is at the center of the living room. Nearby, the Big Sioux River — where Bob fished as a boy — runs rich with Walleye and Bass.

 A half hour south, a job awaits at the VA Hospital in Sioux Falls.

Robert James Riley. It’s time for him to come home in a car, not a box.

Editor’s note: Bob was reluctant to mention his children because of the guilt of failing to be a good father and out of respect for their wonderful mother and loving stepfather. The editor strongly encouraged him to include his children in this story, hoping that the passing of time would make forgiveness and reconciliation possible. — Dennis Cauchon, Editor, The Clemency Report

Click to sign Bob’s petition

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