Serving as the boundary between two street grids that run diagonal to one another, the major commercial thoroughfare of Market Street lends itself naturally to flatiron buildings. And up until the end of the 20th century, the original Phelan Building was one of its most prominent triangular edifices. 

Unfortunately, the grand Phelan Building was destroyed (along with countless other structures) in the 1906 earthquake and fire. After the disaster the son of the building’s original owner decided to replace it with an even grander version to serve as a symbol of the city’s rebirth.

This second Phelan Building was one of the earliest office buildings to be rebuilt after the catastrophe. It was finished on September 1, 1908, and advertised in a gorgeous brochure with such amenities as integrated motors and a building-wide in-wall vacuum cleaning system. “Cars pass the door every minute,” the brochure boasted—and they still do today, as one of the three walls faces Market Street.

An unusual feature of the building was the inclusion of a small penthouse. Originally adorned by a rooftop garden, it was used by James D. Phelan himself to entertain dignitaries. It later served as a photography studio in the 1960s before being abandoned sometime in the 1980s. 

Once one of the informal centers of San Francisco’s jewelry business, the building is now entirely converted to open floor format, and hosts a number of internet startups.