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According to Adriano Martínez, a former executive of Habanos SA, in Min Ron Nee's Illustrated Encyclopedia of Post-Revolution Havana Cigars, the Trinidad brand was first produced in 1969 at the El Laguito factory in Havana.

In the early 90's, the cigar received much attention in Cigar Aficionado after an interview with Avelino Lara (formerly the manager of El Laguito and, as of this writing, a producer of cigars for the Graycliff Hotel in Nassau, Bahamas). In the 1992 interview, Lara claimed that Trinidad was an ultra-exclusive brand that only Fidel Castro was authorized to hand out as diplomatic gifts. Lara also claimed Trinidads were of a higher quality than the much-lauded Cohibas that had formerly been diplomatic exclusives before their mass-market release in 1982.

Two sources have contradicted Lara's claims: President Fidel Castro himself and the afore-mentioned Mr. Martínez. In an interview with Cigar Aficionado, when asked about Trinidads, Castro stated that he only gave Cohibas away as diplomatic gifts. In the Illustrated Encyclopedia, Martínez stated that Trinidads were actually a lower-level diplomatic gift than Cohiba cigars, made with a tobacco blend similar to that used in the Cohiba vitolas, but without the third barrel fermentation that Cohibas receive.

In 1995, Cigar Aficionado hosted the Dinner of the Century in Paris, France where, among other rarities, the guests became the first outside of diplomatic circles to taste Trinidad cigars.

In February 1998, the Trinidad brand was released for public consumption at an opening ceremony in the Havana Libre Hotel in Havana. The initial release was only in one size: the Fundador. Though Martínez and others maintain that the blend did not changed in the transition from a diplomatic gift to a mass-marketed cigar, the size did. The diplomatic Trinidads only came in one size, that of a Laguito No. 1 (the same as the Cohiba Lancero). The Fundador instead comes in a new size with a factory name of Laguito Especial, the same length as a Laguito No. 1 but with a ring gauge of 40 instead of 38.

In November 2003 at a black tie dinner hosted by UK importer Hunters & Frankau at the Hilton Park Lane in London, England, three new sizes were debuted for the Trinidad line, the Colonial, the Rey, and the Robusto Extra.