When I first met Patrick Symmes he was in the back of a Havana bar, sharing a joint with a couple of hookers. The meeting did not take place in person but through a 1997 Harper’s article on Cuba, and I admired his verve and above all his honesty. Plenty of journalists write about visiting Cuba, but this was the first time one admitted joining and enjoying the sleaze—and there is plenty to join and enjoy.

Now Symmes has written a serious book on Cuba, seen through the prism of the alumni of Colegio de Dolores, a Jesuit school in Santiago de Cuba where Fidel and Raul Castro were enrolled. Skipping from alum to alum, Symmes also travels through the history of the revolution and the personality of its leader.

Fidel Castro comes across as a complex character, half reckless courage and half calculated manipulation. While some of his actions have been daring, the Cuban leader himself has wrought the mythology of his personality and that of the long-lived and tattered revolution he has led.

The alums are a mixed bunch. The school served the Santiago elite, so not surprisingly, many have gone into exile, such as Luis “Lundy” Aguilar, who was Fidel’s classmate and for a while his friend. In exile, he served as op-ed editor of and frequent contributor to El Nuevo Herald. Aguilar, Symmes reports toward the end of his book, has fallen to the vicissitudes of old age—in his case Alzheimer’s—as have many of the “Dolores boys,” including Castro. A handful of alums remained in the island, with various degrees of fealty to the regime.

Symmes’ reporting leads him to learn that Raul Castro—whose school nickname was The Flea—was then, as until recently, Fidel’s second fiddle. The writer reconstructs the rhythms of life in the school and in Santiago, Cuba’s second city and eternal rival of Havana but at heart a provincial town.

Symmes has no political ax to grind. In his Harper’s article he called exiles “history’s losers”; here he is merciless in his description of the failed and corrupt revolution, writing that he figures he won’t be allowed back into Cuba. He places the Revolution in perspective by comparing Cuba’s woes to those of other Latin countries, something Castro’s enemies seldom do.

Told by some Cubans about horrific slums, he is driven to what he expects will be a shocking sight. Instead, the sanguine Symmes breaks into giggles. He has seen the worst of the region’s favelas; these “slums” appear to him like clean suburbs. The experience prompts him to ask the inevitable question: Is the only choice for a country such as Cuba a repressive government that maintains a minimum standard of living, no matter how far from its goals, or “freedom” with the truly abject and socially unjust conditions prevalent in other Latin countries? “Which was better?” Symmes writes. “Repression and control, or freedom and chaos?”

He has no answer. What he has is heart, and his observations are on the money. A travel writer, Symmes delivers a muscular prose and a keen sense of detail. He lacks the erudition and intellectual perspective of, say, David Rieff, who has written extensively on Cuba and Miami. But Symmes’ unabashed raffishness keeps him afloat in the treacherous wetlands of Cuban politics and culture.

Cuba, as one of the island’s writers illustrated in a novel, can be a quagmire. Outsiders are easily seduced by its sizzle and then caught up in its erotic webs of intrigue and contradictions. But sooner or later, they sink. Symmes comes close, very close, to getting it right. He notes the most obvious signs of the exiles’ nostalgia-fed exaggeration about the old times. But he does not know such exaggeration has been ridiculed for decades, including how-many-Cubans-does-it-take-to-change-a -lightbulb jokes. (Nor does he seem to register that Lundy Aguilar’s famous humor piece, The Prophet Speaks of the Cubans, is a spoof of Khalil Gibran’s The Prophet.)

And he fails to see, because he only knows Castro’s Cuba, how such exaggeration is based on a reality the revolution has practically wiped off the map. Cuba before Castro was full of corruption, injustice, tyranny, violent instability. It was also full of a sweetness that was as real as it was fragile and mortal.