The heels of Charles Long’s shoes gave out somewhere along Telegraph Avenue.

Long had just crossed the stage at Memorial Stadium, newly minted as UC Berkeley’s top graduating senior, and was trying to make the 15-minute walk to the restaurant down the street where his family had secured a table. It took him over an hour. Strangers kept stopping him. 

Then, as his feet finally found a path through the throng, the soles of his Stacy Adams dress shoes — a pair held in reserve for years in his late grandfather’s closet and barely worn — began to separate.

The heel came loose. Then it slapped against the pavement with each step.

Clap. People were still stopping him. Clap. Fellow grads were asking for selfies. Clap. They just wanted a quick word.

“I’m having to rip the heels off my shoes,” Long said, “and people are still trying to stop and talk to me.”

Few people who knew Charles Long at 18 — arrested, jailed, his Navy dreams dissolved overnight — would have predicted that at 43 he would stand at UC Berkeley’s spring commencement last weekend and deliver the student address alongside the former labor secretary under President Bill Clinton while wearing his late grandfather’s shoes. And not only that, he was delivering that speech as winner of the University Medal, awarded to UC Berkeley’s most distinguished graduating senior.

“I’m not pursuing the University Medal because I need a title,” the 43-year-old wrote in his medalist essay. “I’m pursuing it because of the story it tells: that Berkeley’s highest honor can belong to someone once written off, who can take their life’s greatest pain, define it with introspection and study, and use it as their greatest asset.”

Laleh Behbehanian, a continuing lecturer in Berkeley’s sociology department who has taught for 23 years, wrote in a letter recommending Long for the University Medal that “his contributions to class discussions, shaped by his own experiences being formerly incarcerated and growing up in the foster care system, had a profound impact on his peers. Charles is a brilliant young scholar whose potential is unparalleled among his peers.”

It was not always clear that Long would have peers like these at all.

Born in the Bay Area, with childhood stints in Oakland and Milpitas, he was arrested at 18 for an assault he maintains he did not commit. What followed was months in jail without trial and a public defender who, he says, seemed disinclined to fight the charges. He accepted a plea deal, not because he was guilty, he said, but because contesting the case felt more dangerous than surrender. 

And he had good reason to believe that; his own father had fought a case rather than plead guilty, lost, and received a far longer sentence. Long was not going to make the same bet.

“I believe the district attorney knew I was innocent but pushed forward anyway,” he wrote. He received a sentence of two years in prison and five years of parole. 

The plea deal was not the end of the punishment. As Long framed it in the essay, it was the beginning of a second sentence. 

His family members moved away from their Silicon Valley home while he was in prison, and without a support network on his release he drifted into stints of homelessness and police harassment. His career prospects often stalled at the checkbox at the bottom of every job application that would acknowledge his criminal record before he could offer a word of explanation.

“When the system denied me opportunity and dignity,” he wrote, “I created both for myself.”

His daughter pointed him toward something larger. Fatherhood, he wrote, revived a vision he had carried since age 5, of becoming a social worker. It was a seed planted by a foster care caseworker who was, for a long stretch of his childhood, the most stabilizing adult presence in his life. 

Long enrolled in community college at 37, maintained a 4.0 GPA while caring for his grandmother during the pandemic, navigated serious challenges related to his daughter’s health, and earned degrees in psychology, sociology, and social and behavioral studies at Moreno Valley College in Riverside County.

His transfer acceptance into Berkeley in 2022 buoyed him beyond academic achievement. “I would spontaneously burst into tears for weeks,” he wrote. “It wasn’t just the fulfillment of a childhood dream; it was redemption.”

It was also a chance to transfigure his firsthand experience and struggle with poverty and the criminal justice system into a way to help himself and others.

His senior thesis, “Love is Contraband in Hell,” challenged the legacy of the Stanford Prison Experiment, finding that where professor Philip Zimbardo in 1971 saw proximity to power producing cruelty, the students Long sent into San Quentin as volunteers came out transformed by proximity to suffering. 

A second thesis, “Degrees Behind Bars,” mapped prison degree programs nationwide into an evaluation matrix intended to shape state and federal policy. Together they make a single argument: that education, directed with intention, can interrupt cycles institutions have long treated as inevitable.

During his commencement speech, Long opened with the idea of the “organic intellectual” who is “grown from the soil of the communities they come from.”

“They don’t study to escape their communities, but to understand, represent, and serve them,” he said. “They turn experience into insight, insight into action, and action into a better world.”

“When I arrived here I carried a story,” Long said, pausing to take a deep breath as tears and emotion briefly overwhelmed him. “I carried a story that I thought would disqualify me from places like this. Now that story is one of my greatest assets.”

A few days removed from that sunny Saturday morning stage, Long was doing what he seldom does in the middle of a day: sitting still. The stretch of campus he moved through on a midweek afternoon was quiet in the way college only gets between graduation ceremonies — after the stadium has emptied but with everything still in place for the next events. He had another graduation ceremony to attend, this one closer to home, about 15 minutes from campus. But for now, there was a seat near Sather Gate and nowhere urgent to be.

It did not last long.

A woman passing by stopped midstride when she recognized him. She explained breathlessly that she had watched his speech live-stream from her couch. She came to Berkeley for her niece’s biology graduation, and couldn’t walk past without saying something.

“I don’t know,” she said, searching for words. “It’s like things just could have gone so far left for you, but you brought it around and you just did the damn thing.”

Long watched her go, then shook his head slowly. “There’s nothing like moments like that,” he said, “to bring a lot of things home to you.”

After next month, his lease ends. He’ll start a gap year with a move to Nairobi, where his partner is completing her master’s degree at Kenyatta University. They keep an apartment there and Long has been to Kenya multiple times and traveled to her village in the western part of the country.

He intends to apply to doctoral programs, and he wants to approach those applications with the kind of unhurried attention that Berkeley, for all it gave him, rarely afforded. “Everything looks much slower out there,” he said of being abroad. “It really gives you time to think.”

He was still, for the moment, wearing shoes with soles intact.