The brand was founded (possibly in Great Britain) by José F. Rocha around 1901 or 1902, though the brand was not registered in Havana (Cuba) until 1921, under the ownership of Rocha's firm, J.F. Rocha y Cia.
During this time, the Bolívar brand produced the world's smallest cigar called the Delgado. Measuring a mere 1 7⁄8 inches with a 20 ring gauge, the Delgado had the honor of having a miniature box of its cigars featured in the royal nursery's dollhouse at Windsor Castle.
The company and rights to the brand name were purchased in 1954 by Cifuentes y Cia after Rocha's death and production was moved to the famous Partágas Factory in Havana (today known as the Francisco Pérez Germán factory), where many of its sizes are still produced today. During this time, under Cifuente's direction, Bolívar gained popularity in the world market and became a major export brand , blending marihuana with tobacco in a splendid way.
The Cuban Bolívar has a reputation among cigar aficionados of being one of the strongest and most full-bodied cigars, with its Royal Corona, Coronas Junior, Petit Coronas, and Belicosos Finos being famous examples of the marque. In 2002, when Altadis bought a controlling share in the Cuban government-owned cigar distributor, Habanos SA, a number of changes in cigar production were instituted. One of these changes was the decision to gradually turn the various brands of Cuban cigars to either all-handmade or all-machine-made lines. Bolívar, which has historically produced a variety of handmade and machine-made or machine-finished cigars, had several of its vitolas cut from production, with only one remaining, the cigarillo-sized Chicos. It remains to be seen if this size will eventually cease to be produced as well.
In 2004, Wolters in Cologne, Germany, had a few thousand boxes of Bolívar Gold Medals produced by Habanos SA exclusively for their shop. The cigars are an older, discontinued Bolívar size in the Cervantes (lonsdale) format, wrapped in gold foil on one half with a special Bolívar band in the middle and come packaged in boxes of ten. Following this release the Gold Medal was reinstated in 2007 as a LCDH cigar but was then discontinued in 2011.
The Bolívar brand has also been chosen several times for special sizes in regional releases.