This article examines the transition of the Puerto Rican operations of the “Tobacco Trust” from a cigarette manufacturing operation in 1899 to an agribusiness by 1911. The Porto Rican American Tobacco Company (PRATCO) created monopolistic conditions by absorbing the two major domestic cigarette factories and their former owners as shareholders. When the American Tobacco Company (ATC) entered the US cigar trade in 1902 in earnest, the PRATCO initiated an enormous expansion. While the trust never became a leaf grower save in Cuba and Puerto Rico, the Porto Rican Leaf Tobacco Company (PRLTC) developed sizable plantations of shadegrown tobacco for cigar wrappers. When the US Supreme Court mandated the partition of the ATC in 1911, the PRATCO emerged as a large US cigar manufacturer with a near monopoly of local cigarettes, and the PRLTC proved to be the major leaf grower.