The Winton Oracle: Then, Now, and Beyond Celebrating 60 Years of Storytelling at De La Salle and Carondelet

In the fall of 1968, when De La Salle and Carondelet were still new schools finding their rhythm, a handful of students armed with typewriters and curiosity decided to create something lasting: a student newspaper. The Winton Oracle—named after the shared Winton Drive campus—was born out of enthusiasm, idealism, and, as an early founding editor Bob Montgomery ‘70 puts it, “a whole lot of trial and error.”

“There wasn’t much structure back then,” Bob laughs. “We just gathered whoever was interested and said, ‘What do you want to do?’ We had one moderator over at Carondelet, Mrs. Gail Jarrah, who taught journalism, and she helped us pull it together. But mostly, we made it up as we went along. If someone wanted to review a play, interview a teacher, or write about what was going on at school, we just did it. That freedom was exciting.”

That sense of freedom was forged in a time of national unrest. The late 1960s were marked by political protests and social change, and even on the small De La Salle and Carondelet campuses, that energy could be felt.

“We had a student who skipped class to join the Berkeley protests,” Bob recalls. “He even brought back a half-exploded tear gas canister as a souvenir! It was that kind of time—students wanted to be part of what was happening in the world. And the Oracle gave us a voice to talk about it.”

Bob wrote and edited some of those earliest pieces—everything from play reviews to editorials on school policy. One memorable article challenged the school’s obsession with GPAs.

“I said there was too much emphasis on grades,” he says. “That didn’t go over great with the principal at the time. But we had an editorial policy: no censorship. If something mattered to students, we covered it.”

Printing the newspaper was its own adventure. “We did all the layout by hand,” Bob says. “Cutting, pasting, choosing type sizes—then sending it to a printer. When those first copies came back, people couldn’t wait to grab one. They wanted to see who was in it, whose picture was there. It created connection.”

That connection is what the modern-day Winton Oracle continues to cultivate. After over a decade of dormancy, the newspaper was revived just a few years ago by a new generation of student journalists—among them Yael Aguilar, Carondelet class of ‘27 and Rayne Gutierrez, De La Salle class of ‘27.

“I joined my freshman year,” Yael says, “and it was honestly the best decision I’ve made in high school. There was so much pride in continuing something that had such a long history. We talk a lot about legacy—how this was something De La Salle and Carondelet students created together more than 50 years ago, and now we’re giving it new life.”

For this generation, keeping a print publication alive in the digital era is both a challenge and a mission.

“The hardest part,” Yael admits, “is getting students to read something that’s not on their phone. But once people see it—once they realize their classmates wrote it—they’re interested. We want it to be relevant, inclusive, and something that reflects what our community cares about.”

Rayne agrees. “We want readers to learn something they wouldn’t just find online,” she says. “If it’s in the Winton Oracle, it should feel personal—something about our schools, our people, our voices.”

Balancing tradition with innovation, today’s staff designs each issue digitally but keeps the original spirit intact.

“If you look at the old editions,” Rayne says, “they’re not that different from ours. The format has changed, but the purpose hasn’t—it’s about connection and curiosity.”

For Bob Montgomery, that continuity is deeply meaningful.

“I look at what the students are doing now, and it makes me proud,” he says. “We started this with a typewriter and some wild ideas, and now they’re writing with more structure and depth than ever. The Oracle taught me how to communicate—and that skill shaped my whole career.”

Bob went on to lead teams in business, serve as president of the Make-A-Wish Foundation of the Bay Area, and later become the first De La Salle alumnus to chair the school’s Board of Trustees. He credits much of that to what began on Winton Drive.

“The Oracle gave me confidence, taught me how to listen, how to ask questions, and how to work with people,” he reflects. “It was the foundation for everything that came after.”

As the Winton Oracle turns another page in its story—one that now spans six decades—its legacy continues to evolve. What began as a bold experiment in 1968 endures as a bridge between two campuses, two generations, and countless student voices still eager to be heard.

“It’s fun, it’s creative, and it’s ours,” Yael says simply. “We’re not just keeping history alive—we’re writing the next chapter.”

See more stories from De La Salle’s 60th year at www.dlshs.org/60for60.