Twenty two years ago this month, I had just completed an exploration of Oakland, California in preparation for an article planned for issue 32 of Roadside. Why Oakland? The story is serendipitous. 

Two-plus-years before, I sat on a four-stop Southwest flight to Seattle from Providence. On the leg between Los Angeles and Oakland, an attractive woman sat down next to me and asked me if the book I happened to be reading was any good. I was not reading the latest Grisham or Stephen King. It was another book about urban planning.

Her name was Darlene Rios-Drapkin (pictured above), and she was a Main Street manager for the Fruitvale neighborhood of Oakland, which was where she disembarked. The plane ride was the start of a cross-country road trip and hers was the first meeting of many I had on that trip back from the west coast. I jotted a mental note to put Oakland on Roadside’s radar as another potential urban exploration feature in the magazine. Then a little over a year later, NPR featured Darlene and her efforts to revive Fruitvale. Now, I made it a priority to get out there, especially in 2000, the year we had a real budget. 

At the time, San Francisco was the epicenter of the tech boom and I wondered if long-suffering Oakland might enjoy some spillover from all the cash pouring into the city. Using Fruitvale as a launching point, I would finally write my story exploring all the little nooks and crannies of the city’s culture in much the same way we did with Syracuse, Cleveland, Portland, Oregon, and Pittsburgh. I spent ten days soaking it all in, and came away hopeful that Oakland — and Fruitvale which would soon see the development of a new transit village around its BART station — would exemplify the concept of urban revival. 

I returned in 2006 for a quick drive-through. Fruitvale got its transit village and all seemed well. I haven’t been back since. 

Most of us know about the crisis affecting San Francisco these days. For the past several years, it has experienced a growing epidemic of homelessness and crime coexisting with an outrageous cost-of-living. It’s so bad that you can find online maps marking the concentrations of human feces on the sidewalks. 

While I’m sure most of the city remains a pleasant experience, the fact that matters descended so precipitously in its core has completely eroded the optimism I once felt for the prospect of revival in our great cities. If it has become that bad in the jewel of the west coast, what hope is there for Baltimore or Cleveland or Buffalo? Or even Philadelphia?

But what about Oakland?

I regret to say that I’m almost glad we never published my story about Oakland. This video, which tours many of the same streets I did, shows why and it breaks my heart.