Cover of São Paulo

São Paulo

The Ugliest City You’ll Ever Love

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São Paulo

By: Brian Winter
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The story of how an “unlovable” city became the powerhouse that reshaped Brazil.

São Paulo is the ugliest city you’ll ever fall in love with.

How in the world did this humble Jesuit trading post manage to overtake its glamorous sibling, Rio de Janeiro, and become the engine of modern-day Brazil—and indeed the premier city of the Southern Hemisphere?

Brian Winter, who lived in São Paulo with his family for half a decade and still returns multiple times a year, leads us through this vast metropolis marked by endless traffic, vertical neighborhoods, and overlapping spheres of wealth and precarity. We discover the city’s deep lineage of immigration and the crucial place of foreignness in its collective identity; the resilience of its historically marginalized communities and the absurd excesses of its upper classes; and the remarkably enduring way families of modest origins can work their way up to fortune, fame, and influence.

Expansive and intimate, São Paulo is the story of a city fueled by ambition and improvisation, by a legendary work ethic and an equally impressive respect for pleasure, and by the abiding faith that anyone, everyone, is welcome.

“São Paulo … when it’s finished, it’ll be pretty.”

©2027 Brian Winter (P)2027 Blackstone Publishing
Travel Writing & Commentary
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