Dennis Lehane’s Live by Night: Island of Misfits

By Wes Newbury

“As far as the writer as an outlaw,” said Dennis Lehane in his Literary Traveler interview,  “we are sort of the square pegs, and the world is the round hole.” Writers are very much the misfits of the world, and although Lehane admits, “they may not make the best of outlaws,” writers relate to outlaws through their shared experience of social incongruity.

Cuba is considered the outlaw of nations—where dreams of outlaws go to decay. Sea walls that once served as protection from pirates crumble into grains of sand. Busted light bulbs trace the letters of old casino signs. American cars from the fifties wheeze past murals celebrating fifty years of communism. “We will overcome,” reads the chipped white paint on decomposed adobe walls.

In Havana, old dreams stand like the decrepit monuments of an outlaw’s reign. Pirates, gangsters, and an exiled band of students have left their indelible legacy on Cuba. And their endeavors have added to the mysticism of the island, and helped to eternalize Cuba as less Place than Idea.

The idea of Cuba appeals to outlaws of all kinds, and writers are no exception. In Lehane’s most recent novel Live by Night, Joe, the protagonist, reflects on the essence of Cuba. He explains, “Habana wasn’t simply a place; it was the dream of a place. A dream gone drowsy in the sun.” Joe relates to this dream—he thinks of himself as an outlaw, a roving individualist who has no categorical identity. Once a punk kid from Boston, Massachusetts, Joe dreams of being a free-spirited maverick, making his own way in the world. He holds onto this dream with wit and determination, but when Joe’s line of business takes him to Tampa, Florida, and eventually to Cuba, his romantic visions of independence begin to melt.

As a student, I spent a semester in Cuba in 2010, and the experience had such a profound impact on me that I struggle to write about it now. Cuba is a place of great contrast and contradiction, where sunlight and shadows find no mutual exclusivity. The island resides somewhere between dark desperation and blinding hope, and these two motifs are thematically significant in most Cuban literature and books set there.

Lehane masterfully uses Cuba as both a place and an idea in Live by Night. By telling a story of a young man’s search for identity in a world that has no place for ambiguity, Lehane has crafted a wonderful addition to the literary picture of an iconic island of misfits.

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