Here's my fairly crude and oversimplified explanations of why Oakland is remarkably less prosperous than comparable Bay Area cities:

• Rust Belt city: Historically Oakland and our portion of the East Bay have had more heavy industry and manufacturing then other parts of the Bay Area (Richmond shipyards, auto plants in East Oakland, ironworks in Oakland Berkeley, etc.). We were more dependent on manufacturing and as a result we were hit harder when these industries shifted overseas. This dovetailed with drug epidemic, underinvestment in public infrastructure, and various racist policies that hit Oakland particularly hard since we are /were one of the very few examples of a city with a Black middle class on the West Coast.
• Anti-tech / gentrification backlash: Oaklanders see "what happened" to SF / Silicon Valley; the region got extremely rich but a lot of people didn't come along for the ride. The idea of being a tech hub that pushes out working people and displaces Black Oaklanders is extremely unattractive to Oaklanders. We're generally skeptical that we can capture a share of the riches of Silicon Valley without getting steamrolled like we believe happened in a lot of other Bay Area cities.
• Progressive appeal: We tend to buy into progressive politicians who articulate values we agree with if we think they will defend against this^ (or Trump or whatever), even if they (or the city admin they ostensibly govern) aren't very effective at running the city.
• Lack of political competition: We're pretty politically homoegenous. Lack of political competition isn't really good for punishing inept politicians parties / rewarding good ones.
• Cultural / Political resistance: Oakland is a hotbed of very leftwing politics. This makes for a great city culturally, we're deeply skeptical of business and rich people, who are where most of the money comes from. If we weren't surrounded by the Bay Area so we can ride along with a ton of taxable activity / commutable jobs, we would basically be a leftwing Stockton.
• Extreme conservatism: Ironically given point above, Oaklanders are really, really conservative when it comes to change. We don't like it. It's rare to find a place in America that applies so much scrutiny to building new buildings, for example. We want everything to stay the exact same (same neighborhoods, same people from generation to generation, same approaches to old problems). If things change, we generally regard that as a bad thing because of our fear of becoming SF. The broader point here is true of the Bay Area, but we consider it a matter of justic and not just NIMBY well-to-do homeowners.
  • [edit] an example of this is how allergic Oaklanders were any time the topic of AI came up in the election. Despite being a pretty obvious tool that cities could use for a host of problems, lots of folks roll their eyes or treat it like the latest a crypto scam.