Venezuelan President Hugo Chávez in the mid-2000s ordered his top lieutenants to work with Colombian Marxist guerrillas to flood the U.S. with cocaine in his government’s efforts to combat the Bush administration, according to U.S. documents obtained by The Wall Street Journal that shed new light on the leftist regime’s struggle with Washington.

The documents, prepared by federal prosecutors from the Southern District of New York, outline for the first time the possible role of Mr. Chávez, an icon of the Latin American left...