And illustration of Oakland with a grizzly bear, old-growth redwood trees, a hot air balloon, and other items that once existed in Oakland but are no longer visible.
Illustrated by T.L. Simons, East Bay Yesterday's "Long Lost Oakland" map is now available as a 500-piece puzzle. Credit: Courtesy of East Bay Yesterday

In 2018, Liam O’Donoghue was trying to make sense of the changes he saw happening across Oakland’s cultural and physical landscape. He was living near downtown Oakland at the time and about two years into producing East Bay Yesterday, his podcast chronicling the region’s fascinating cultural, political, and natural history. 

So it was natural that O’Donoghue turned to history as a means to process the changes he was witnessing, at a time when more and more people in the city were having conversations about displacement and gentrification. He sat down and created a map depicting “long lost” objects, both natural and man-made, that are no longer visible in Oakland. The map became a canvass for O’Donoghue’s creativity—and ultimately, an educational accompaniment to the audio stories he was creating for the podcast.

“The thing that made me want to map in the first place was my own disorientation and anxiety around how Oakland was changing,” said O’Donoghue. “I wanted to create a map that had these features that represented other [points] in Oakland’s history when things were changing really rapidly.” 

The sites and objects now depicted on the Long Lost Oakland map have since been examined thoroughly in the podcast. But as the show’s name makes clear, East Bay Yesterday isn’t solely focused on Oakland’s history. Episodes about the formation of the Afro-American Association, the Oakland-Berkeley Hills Fire of 1991, and local Latino history are just a few topics among many—the podcast now boasts over 100 episodes—that touch on Oakland, Berkeley, Richmond, and communities beyond.

As the podcast has grown in popularity, it has evolved to become a platform for web articles and local panel discussions about Oakland’s history. O’Donogue also plays the role of event host for one of the hottest tickets in town: East Bay Yesterday’s Oakland history boat tours. Put on in partnership with Fish Emeryville, the tours regularly sell out weeks in advance.

Now, the map, which is illustrated by T.L. Simons, has been turned into a puzzle with the help of the Oakland Puzzle Company. It can be pre-ordered on the puzzle company’s website. 

“Puzzles are absolutely timeless and there has been a resurgence in families and people doing jigsaw puzzles,” said DeAnna Tibbs, who co-founded the Oakland Puzzle Company with her brother Dave Tibbs in 2020 during the pandemic.

O’Donoghue and DeAnna Tibbs met years ago while campaigning to get a mutual friend released from prison. Turning the map into a puzzle has been a shared vision of theirs ever since.

“The artwork is absolutely perfect for a puzzle,” Tibbs said about the Long Lost Oakland map.

East Bay Yesterday and the artist will receive 30% of the proceeds during the presale and 10% thereafter. 

Oakland Puzzle Company doesn’t have the capacity to produce specific puzzles in small quantities due to the production and printing costs, said Tibbs. But for local artists and creatives looking for new ways to earn money, she said puzzles can offer an opportunity in part because they are “more viable than art on a wall” for many consumers.

“Our mission is to bring jobs to Oakland and support artists and organizations by both raising funds and awareness about the work that they’re doing,” said Tibbs. “I feel like it’s an economic opportunity that is also very creative.”

The Gold Rush, the Great Depression, World War II, and the 1906 earthquake that caused many San Francisco residents to migrate to Oakland are all historical points referenced in the Long Lost Oakland puzzle’s imagery. 

“If you look through history, Oakland has never been standing still,” said O’Donoghue.

Since it was released, the Long Lost Oakland map has been available to educators from any grade level to use, for free. O’Donoghue hopes the new puzzle will also be a tool for educating people about Oakland’s history; the Oakland Puzzle Company has partnered with universities and museums to help sell it. 

“The purpose of the project was to get people to engage with local history and kind of wonder about the different features on the map,” said O’Donoghue. “What better way to spark some curiosity than to put the maps into a format where people are going to be staring at it for hours at a time?” 

To pre-order the Long Lost Oakland puzzle, visit East Bay Yesterday. Artists interested in turning their art into a puzzle can contact the Oakland Puzzle Company for more information. 

Brandy Collins is a writer and public services advocate, born and raised in the Bay Area. She is a 2019-2020 cohort graduate from the Maynard Institute for Journalism, a correspondent for Oakland Voices, a blogger, and the funny one in numerous group chats. She is concerned with civic engagement and leadership development toward making public works more efficient for the people. Brandy is full of Scorpio magic and a self-proclaimed Professional Aunty. Follow her on Twitter @MsBrandyCollins or Instagram @story_soul_collecter.