The man who wants back into San Quentin

In order to teach, Bill Smoot had to leave everything behind. His wallet, cash, credit cards, and chewing gum — everything but his car keys, ID, and course materials.

From Berkeley, Smoot drove 25 minutes over the bridge to the San Quentin Rehabilitation Center, where he waited by the outer gate with a small group of professors. Then their little procession began, past the first guard, into the main gate, through the sally port with its steel bars and bulletproof Plexiglass, and into the heart of California’s most infamous prison.

Strangely, though, it was, in parts, quite beautiful. Green lawns. A small garden. A chapel. Men tending to rosebushes. It looked less like a state prison than the cloisters of a monastery hidden behind medieval fortifications. But going a bit further on, there emerged the familiar landscape of 20-foot walls, guard towers, rifles, razor wire, and men in blue pacing the yard. Sometimes though, a friendly voice would break the heavy air, “Hey, Smoot!”

By all accounts, the convicts of San Quentin who became Smoot’s students adored him. The feeling was mutual. For 14 years, Smoot kept making the trip back, over the bridge and through the prison’s tediously layered security to return to his students. But these days, he no longer makes the trip. Earlier this year, Mount Tamalpais College fired Smoot after he published a fictional novel about a teacher at San Quentin and a prisoner who finds hope in the classroom before escaping — with the teacher’s help.

Most of the teachers at Mount Tamalpais College, the accredited liberal arts college inside San Quentin, are, like Smoot, volunteers. But even though he wasn’t compensated, Smoot treated the job as if it paid six figures, exploring ideas in literature and philosophy no differently than he had anywhere else over his 50-year career, which spanned from UC Berkeley to the Castilleja School. “One of the keys to teaching effectively in prison,” he says, “is to recognize that it’s not that different.”

This may be the most radical thing Smoot believes about prison education — that it should be like education anywhere else. “They deserve a real college,” he says, adding, “There are already statistics about the recidivism rate of people who take college courses in prison versus those who don’t.” Indeed, multiple studies have found that prison education significantly lowers recidivism.

But for Smoot, education is not valuable only because it produces better outcomes. It also demands intellectual seriousness. A real college must expose students to difficult ideas and honest inquiry, challenging them to grow and be better, even if those ideas may make institutions uncomfortable. What else does academic freedom mean?

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This belief was forged long before he began teaching at San Quentin. In 1968, he was editor-in-chief of Purdue University’s The Purdue Exponent, and under his leadership, the paper became involved in reporting on and advocating for the issues of the day, from Vietnam and the civil rights movement to campus protests. But Purdue was a conservative campus. In fact, the entire state of Indiana was conservative. The school administration wanted something closer to a campus showcase; a public relations organ with pinnings, glee clubs, and no front-page evidence that the 1960s had reached the city of West Lafayette.

When Purdue’s president unilaterally removed Smoot as editor, the student staff revolted, and by the following Monday, Smoot announced in what he would call his “Tennis Court Oath edition” that he would continue in the role. Students, faculty, national organizations, and the press rallied. The administration could either send police to seize the newspaper office or back down. It chose the latter. Smoot was victorious. But more than half a century later, he would find himself defending education once more in a remarkably similar fight.

The escape plot

The compromise that ultimately cost Smoot his classroom had nothing to do with his teaching. It had to do with his book, San Quentin Exodus, published in June, about a fictional white suburban prison tutor with a Nancy Drew obsession and a black inmate whose life has gone terribly wrong. The book includes an escape plot, as well as descriptions of the many decent-hearted men Smoot came to know in Mount Tamalpais classrooms during his time there.

“I see men who have done very bad things years ago,” he once wrote, “now trying to make themselves better. Convicted felons take classes, commit themselves to self-help groups, organize peace days on the yard, and walk to raise money for breast cancer care. Those with the necessary clearance fight wildfires.”

Smoot thought prison higher-ups might like the book. After all, it doesn’t trash San Quentin or prisons in general. It doesn’t depict guards as monsters or prison administrators as sadists. Indeed, according to Smoot, the book shows the very thing California officials say they want the newly renamed San Quentin Rehabilitation Center to represent: rehabilitation. Specifically, “the California model” with its drama workshops, peer mentorship, and life-changing classrooms.

But instead, says Smoot, the escape plot “freaked out” Mount Tamalpais College President Jody Lewen. He had given her an advance copy, and he says she worried that the California Department of Corrections and Rehabilitation might react badly. However, Smoot says he later learned that no one at CDCR had actually read his novel in full. When he spoke to the warden, Chance Andes, Smoots says he seemed to be grasping at reasons to justify the termination, eventually settling on the fact that Smoot hadn’t gotten permission to use “San Quentin” in the title of the book, despite the fact that the prison is a household name and regularly appears throughout popular culture.

Nor is the book a manual for escaping prison. The fictional scenario he describes in his book depends on a highly specific combination of factors that are unlikely to ever align for success: an accomplice obtaining the right UV stamp from a party store, widespread COVID masking that makes identities easier to obscure, and prison staff failing to closely verify the identities of people leaving the facility.

But in Lewen’s email to Smoot announcing the decision to fire him, a different concern becomes clear. “When you first started as a volunteer,” she wrote, “you received that list of institutional rules, as part of a very in-depth, hours-long presentation by me on institutional rules, regulations, and culture.”

Lewen then explained that she has spent the last 25 years trying to convince San Quentin officials, as well as correctional administrators nationwide, that their concerns about such college programs are unwarranted and that, “as college instructors are sufficiently vetted, trained, and supervised, they will not disregard the rules of the institution and undermine anyone’s safety.” But, she told Smoot, his book does exactly that because it used “San Quentin” in the title, “created an actual threat to safety and security,” and “fulfilled the most negative stereotypes of volunteers: not just that they do not understand the rules and regulations of the institution; but that they do not care about them and will flout them at will.” (Lewen did not, however, cite the specific rule or rules in question.)

As a result, she said, while expressing regret at the loss of a beloved teacher, Smoot could not be allowed to continue working at the school. And just like that, San Quentin’s gates closed on one of its best professors. But it would be easy, and wrong, to tell this as the story of a censorious bureaucrat silencing a brave teacher. It isn’t.

Lewen is not the villain one might imagine. Heterodox Academy profiled her as a member of the group who wants to bring heterodox speakers inside so her students can engage with broader societal issues and conversations. She became involved with the school after attending a conference on psychoanalysis, where she ended up sitting next to one of the people who helped found San Quentin’s college program. Soon, Lewen began co-teaching a communications course at the school. “I fell totally in love with it,” she told Heterodox Academy. “These were adults who really wanted to be in college — incredibly diverse intellectually, politically, demographically. Intellectually, it was so stimulating.” 

But Mount Tamalpais College’s stated commitments to academic freedom track with a priority to provide expressive rights to its faculty and students by offering the same rights that most other colleges do. Its General Catalog promises to protect “the broadest possible latitude to speak, write, listen, challenge, and learn.” Mount Tamalpais proclaims “debate or deliberation may not be suppressed just because the ideas put forth are thought by some or even by most members of the college community to be offensive, unwise, immoral, or wrong-headed.”

These are noble promises. But if Mount Tamalpais wants to be seen as providing a credible college education to the inmates of San Quentin, it must normalize enforcing the principles of academic freedom that undergird that credibility. College professors, after all, are prone to writing books. Sometimes those books are controversial. They might name real places, and they might make administrators sweat. They might write novels with characters who do alarming, illegal, morally complicated things. Faculty’s freedom to do this is part of the fabric of the higher education experience at just about every college in America. If San Quentin wishes to deliver a comparable education within its walls, how can it treat Smoot’s book any differently?

FIRE wrote to Lewen explaining the importance of Smoot’s case for principles of academic freedom at the budding institution, and asking for clarification on the rules he may have broken. If there’s one thing a prison can be counted on to have, it’s a rulebook.

We received no reply. 

Prison dreams

During the pandemic, San Quentin shut down educational programming, with no online classes. Smoot missed teaching there so much he began dreaming about it. He pined for his classroom at San Quentin, and in his longing to be back in, he began to build the idea of a tutor who wondered about getting out. The prisoner character emerged from his mind fully formed from years of experience with countless men who fit the description. It came easy. He wrote the first draft in six months.

But the deeper engine for the book was not the mechanics of escape. It was the society of men he discovered in the classroom. In a 2013 essay for Salon, Smoot described assigning Homer to men he feared might dismiss an ancient Greek king as irrelevant to their lives. Instead, he wrote, Odysseus, the man “much turned” and “much turning,” made immediate sense to men whose lives had turned, and been turned, again and again. When Odysseus gazed across the sea and wept for home, the classroom fell silent. From San Quentin, incarcerated men can see San Francisco Bay.

When the class moved from The Odyssey to The Catcher in the Rye, some students initially dismissed Holden Caulfield as a rich kid wasting opportunities they never had. But the book, with its universal concerns about authenticity and self-actualization, eventually got under their skin. Smoot remembers one middle-aged black man serving time for murder quietly realizing out loud, “I’m like this dude.”

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A few weeks later, one student returned from a medical appointment, absolutely glowing. He had talked with a nurse about Holden’s obsession with the ducks in Central Park. “She remembered the part about the ducks on the pond,” Smoot recalled him saying. “We talked about that.” This man had stumbled upon one of the greatest gifts of literature — human connection — and Smoot had helped give him that. More than this, Smoot had given the man “a seat at the cultural table.”

But of all his memories there, one of Smoot’s favorites is of an older student from the Mississippi Delta who had never gone to school. For much of his life, the old man had been illiterate. In prison, the chaplain taught him to read, but he never made much use of it. Then he landed in Smoot’s class, where characters in books were discussed and debated the way men in the yard talked about women or sports. Years later, the old man found Smoot crossing the yard one day and his face lit up with pride. He had spoken to his daughter on the phone the night before. He had told her he was reading Shakespeare now.

To understand what San Quentin and Mount Tamalpais lost in firing Smoot, start there. Start with a man who could once barely write his own name, now sharing with his daughter whatever wisdom he learned from the greatest playwright in history. Or think of the student who could talk to a nurse about Holden’s ducks. Or the student who wrote, after taking Smoot’s class, “I had a hunch there was more to my story. Now I know I was right.”

Second acts

To be clear, Smoot has no grudge against Mount Tamalpais College or its leadership. Quite the opposite. He speaks of Lewen’s role in building out the college program and saving it from budget shortfalls with real admiration. He describes with respect how Warden Andes is a hard worker who rose through the ranks from an entry-level correctional officer job. Smoot knows the college’s work matters, and he believes that it is run by people doing their best within a complex system. He knows San Quentin is politically complicated, and that there are people inside and outside the prison who think free college for incarcerated people is outrageous.

But to him, that’s exactly why principle matters, and he hopes the school will reconsider, for the sake of the one thing it exists to serve: its student body. In her email to Smoot, Lewen herself described the decision to fire him as “a huge loss to us and above all to our students, given your tremendous contributions as a teacher and beloved colleague for so many years.”

Gifted and passionate teachers are incredibly hard to find. Even more so those who will devote themselves to prisoners — and for free.

San Quentin has long been a site for reinvention and artistic breakthrough. Merle Haggard was incarcerated there when he saw Johnny Cash perform for the men inside, a concert he later credited with helping turn him toward music. Years earlier, the Actor’s Workshop of San Francisco brought Waiting for Godot to the prison, helping inspire the San Quentin Drama Workshop, an early landmark of American prison theatre. And a little over a decade ago, Joyce Carol Oates taught a creative writing class there. Throughout its history, Smoot says, San Quentin has been a place of second acts.

Now, after 14 years, the gates that opened for Smoot twice a week have closed. The clang is familiar. But this time the man on the wrong side of the gate is not trying to break out. He is asking to be let back in.