“It is a 40-square-block island of poverty and squalor.” The Tenderloin remains one of the seediest neighborhoods in San Francisco, mostly unchanged despite gentrification and an influx of tech money into the city. Can the neighborhood change—and just as importantly, should it?

“If there is one ironclad rule that governs cities, it’s that money and poor people don’t mix. Once money appears, poor people disappear. Most American cities used to have Tenderloin-like neighborhoods downtown, but in almost all cases, those neighborhoods have been gentrified out of existence. Take New York’s Bowery, a name synonymous with flophouses and alcoholic despair as recently as the 1990s. Today it gleams with luxury hotels, shops, galleries, and museums. Or Los Angeles’ downtown, long a skid row Siberia, now a bustling yuppie dreamscape. Similar changes have occurred in cities as disparate in size and disposition as Vancouver, London, San Diego, and Dallas.

“By rights, the TL ought to be suffering the same fate.”