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In the opening pages of his magisterial Bay Area history, Imperial San Francisco, historian Gray Brechin presents his book as an attempt “to answer the question raised by the kind of cities we build today: Are they worth it?” It’s a deceptively simple question, and it reemerges when we discuss San Francisco and its discontents.

From the city’s earliest days, visionaries looked at San Francisco and saw an heir to Rome. Brechin points to Army scout John C. Frémont, who said he named the bay’s mouth “Chrysopylae (Golden gate) on “the same principle that the harbor of Byzantium (Constantinople afterwards) was called Chrysoceras (Golden horn).”

Brechin also discusses Emanuel Leutze, who painted a mural on a wall in the House wing of the Capitol called Westward the Course of Empire Takes Its Way, which depicts settlers seeing California for the first time. “To Leutze’s cultivated sensibility, these were more than settlers entering California,” Brechin writes, “they were both the Israelites entering Canaan and the holy family of the New World.” Brechin describes a party attended by Leutze where the painter...