Carlos Caballero did not start lifting weights until he was 24 but, over the course of his weightlifting career, he won 12 Colombian national championships, two South American championships, and two Central American and Caribbean Championships, all as a middleweight. He competed at two editions of the Olympic Games, but did not win a medal in either 1956 or 1960, and was also selected for the 1964 Tokyo Games, although he did not actually participate, due to budget cuts that prevented him from travelling. He did not retire from active competition until 1970, after which he worked as a coach.