I think the catch-22 is that you'd need a lot of money to run outside of the political system, but SF voters are anti-capitalist (at least, a fair number are) and wouldn't elect a rich person. Of course, Pelosi has $58mm, but she didn't earn it through something big and impressive, but through normal sketchy congressional investment dealings.
> I think the catch-22 is that you'd need a lot of money to run outside of the political system, but SF voters are anti-capitalist (at least, a fair number are) and wouldn't elect a rich person.
San Francisco has a history of electing wealthy people to public office. Reality disagrees with your stereotypes.
She made a lot of money from various non-public stock deals, such as Visa, which were pretty shady. A lot of people in congress do.
Marital wealth is less "obvious" to voters. Voting in a person who actually made a bunch of money through business is much more overt. Inherited wealth is also safe by comparison.