I. The Banker’s Tobacco Kingdom: 1843-1844

Upmann’s initial business model was unexpectedly elegant: he placed premium cigars in refined cedar boxes (Cedar Box) and sent them to European clients together with the trade correspondence of Gravenhorst & Co. This method of combining business exchange with premium cigars created a remarkable brand effect among Europe’s upper classes in the mid-19th century. The European aristocrats who received these wooden boxes unconsciously began to order more from Havana on their own initiative.

By 1844, Upmann had officially opened his own cigar factory in Havana, and the H. Upmann brand was formally established. He was not only a cigar manufacturer, but also an innovative promoter of cedar-box packaging. This seemingly simple packaging strategy completely changed the image of high-end cigars in 19th-century Europe, and also made H. Upmann one of the founders of the packaging tradition of "boxed cigar export," which remains an industry standard to this day.

II. Seven Gold Medals and Royal Recognition

The quality of H. Upmann was soon recognized in objective evaluations. The brand successively won seven gold medals at multiple international exhibitions. These honors are still printed in gold filigree on the box-lid artwork of H. Upmann today, appearing together with Hermann Upmann’s handwritten signature.

The gentlemen’s clubs of Victorian Britain, the Prussian court, the upper society of France: H. Upmann became one of the most widely known Cuban cigar brands in Europe in the second half of the 19th century. The seven gold medals were not only honors, but also the brand’s most persuasive sales tool, allowing every new customer seeing an H. Upmann box for the first time to establish trust in its quality even before opening it.

III. A Change of Family Ownership: From Menéndez to Nationalization

The turmoil of the 20th century had a profound impact on H. Upmann. In 1922, due to a financial crisis in the banking business, the brand passed through several hands and fell under the control of a British importer. In 1937, the Alonso Menéndez family, which founded Montecristo in the same year, acquired H. Upmann, creating a rare dual-brand situation in Havana cigar history: the same family simultaneously controlled two Cuban brands that were among the most popular in the European market at the time.

In 1960, the Castro government completed the full nationalization of the tobacco industry, and H. Upmann, along with other brands, became an asset under Cubatabaco. Today, the Cuban version of H. Upmann is supervised by Habanos S.A. and produced at BSM (Briones Montoto Factory). The factory code "BSM" in the box-bottom factory mark is one of the important bases for identifying authentic products.

IV. A Presidential Connection: JFK and the 1,200 Before the Embargo

The historical status of H. Upmann reached a dramatic climax late one night in February 1962.

President Kennedy’s press secretary, Pierre Salinger, received instructions from the President to search the Washington market as much as possible for H. Upmann Petit Upmann small cigars before the U.S.-Cuba trade embargo order was signed. Salinger went around overnight and ultimately brought back 1,200. The next morning, Kennedy signed the embargo order, and Cuban cigars became legally prohibited for U.S. citizens from then on. This anecdote is examined in detail in the W Cigar Bar Cigar Bible article "JFK and the 1,200 H. Upmann."

V. Key Vitola: A Modern Line Led by Sir Winston

The core Vitola series of H. Upmann covers the full spectrum from quick appreciation to long-format enjoyment:

Sir Winston: 7 5/8 × 47, Churchill format, 194mm in length. The brand flagship, with a burn time of more than 90 minutes. Cream, cedar, and light woodiness form three layers of complexity, making it a standard test question at the aficionado level.

Connoisseur No.1: 55 × 178mm. The generous ring gauge brings solid bunching density, while a woody base note and creamy sheen interweave in the middle and final sections. It is the most technically demanding Vitola within the H. Upmann line.

Half Corona: Ring gauge 44, a quick-burn format of about 15 minutes. It condenses the complete H. Upmann flavor with remarkable density, making it a fitting choice for a business lunch break or a waiting interval.

Magnum 46 / 50 / 54: A large-ring series launched in the 21st century, aimed at the modern market’s preference for thick cigars. Magnum 54 has a ring gauge of 54 and a length of 140mm, making it the widest regular production format in the H. Upmann series.

No.2: Piramides format, 52 × 156mm. The pointed head design makes the flavor of the first third especially rich, and it is a high-value entry point for those first entering the world of Figurado.

VI. Flavor Coordinates: A Moderately Light Havana Gentleman

Within the strength spectrum of mainstream Havana brands, H. Upmann belongs to the lighter side of "Medium," forming a clear contrast with the Full Body of Partagás or the Full+ of Bolívar. This positioning makes it an ideal path for advancing beginners, and also gives experienced enthusiasts who prefer a lighter style a long-term home.

Typical H. Upmann flavor profile:

• First section: Elegant creaminess, slight nuttiness (almond, peanut)
• Middle section: Cedar wood aroma, a small amount of white pepper
• Final section: Deepened creamy base note, occasional cocoa finish

Overall burn is even, the sense of oils is sufficient, and ash cohesion is at a medium level among Havana brands.

VII. Selection and Storage Recommendations

When acquiring the Cuban version of H. Upmann, it is recommended to confirm the box-bottom markings: factory code BSM, three-letter month code, and the last two digits of the year. Matching this with certification from regular channels (PCC / Casa del Habano) can effectively avoid counterfeits.

It is recommended to let it rest in a Humidor at 65-68% RH for at least 3 months before appreciation. Long cigars such as Sir Winston are recommended to be stored for more than 1-2 years, allowing the tobacco leaves to fully integrate.

Conclusion

H. Upmann is the brand in Havana with the strongest "gentleman banker temperament": restrained, precise, never ostentatious, yet revealing remarkable depth on the occasions when it is most needed. From the Bremen trading firm of 1844 to the 1,200 before the Kennedy embargo, H. Upmann has always stood together with history’s most important moments. For members of the W Cigar Bar Gentlemen’s Club, H. Upmann Sir Winston is the black tailcoat that must not be absent from the wardrobe: understated, proper, and never out of style.

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Source of stock: Cuban cigars from the four major official channels (PCC authorized dealers・Cuban official state-run stores・Swiss general agent・Spanish general agent).

LUBINSKI accessories official website: https://cigarclub.tw/

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W Cigar Bar Gentlemen’s Cigar Lounge, written and planned by Cigar Prince Wilson Tsai.