The Shadow of the Shadow follows four men who meet to play dominos in a hotel bar in Mexico City in 1922. They are a motley group—a gun-toting poet who makes a living writing advertisements for patent medicine, a radical Chinese-Mexican union organizer, a lawyer who represents prostitutes, and a newspaper crime reporter who churns out pages of copy "like links of sausage in a chorizo factory."

Left to their own devices, the group would have waited out Carranza's presidency in their own quietly besotted fashion, ignoring the betrayal of the Mexican Revolution. But they witness a series of strangely related murders and begin to suspect a conspiracy involving the oil-rich lands of the Gulf Coast, greedy army officers, and American industrialists.

Critics have hailed The Shadow of the Shadow as the best of Paco Ignacio Taibo II's historical novels. Issues of oil, American imperialism, extortion, and government corruption give the novel a distinctly contemporary ring.