1843-1844: Banker Hermann Dietrich Upmann Lays the Foundation of a Cigar Empire

The Personal Legend of Hermann Dietrich Upmann

Hermann Dietrich Upmann (May 16, 1816-1894):

• Born in Bremen, Germany
• Banker background - received a complete European commercial education
• Arrived in Havana in 1843 - handled business for the German import-export company Gravenhorst & Co.
• Discovered the potential of the Cuban tobacco industry - decided to stay and start his own enterprise

Hermann Dietrich's professional trajectory:

• 1843: Arrived in Havana and handled business for a Bremen company
• 1844: Purchased the cigar factory at 85 San Miguel Street and established H. Upmann & Co. bank
• From the 1850s onward: H. Upmann cigars and banking operations ran in parallel
• 1894: Passed away in Havana at the age of 78

The Dual Commercial Structure of H. Upmann in 1844

In 1844, Hermann Dietrich simultaneously did two key things widely recognized in the industry:

Event 1: Purchased the cigar factory at 85 San Miguel Street

• Located in Old Havana, the core district of the tobacco industry
• The H. Upmann cigar brand was officially established, and its first products appeared in 1844
• The factory site is still widely circulated in the industry as the origin point of H. Upmann

Event 2: Established H. Upmann & Co. bank

• Mainly served clients in the Cuban tobacco industry (tobacco merchants, manufacturers, exporters)
• Bound the cigar industry and banking into a single commercial empire
• One of the most important banks in 19th-century Cuba, later expanding into an international bank in the early 20th century

This dual commercial structure (banking + cigars) is regarded by industry consensus as one of the rarest business combinations in 19th-century Cuba, and it shaped H. Upmann's gentleman positioning for the following 80 years:

From the very beginning, H. Upmann cigars were "gentlemen's cigars for bankers, merchants, and diplomats", not tobacco smoked by ordinary workers over beer.

Cedar-Box Cigar Packaging: Hermann Upmann's Historic Invention

Hermann Dietrich Upmann is widely credited in the industry with inventing "cedar-box cigar packaging", the standard packaging format of the modern cigar industry.

Historical background:

• Before the 1840s: Cigars were usually sold in paper wrapping, sacks, or loose form
• To provide bank clients with "luxury gift-grade" cigars, Hermann Dietrich invented packaging in Spanish cedar boxes
• The aroma of cedar is compatible with cigars and does not contaminate their flavor
• This packaging design has since become the global standard of the cigar industry, unchanged for 180 years to this day

It is widely circulated in the industry that early H. Upmann boxes from the late 1840s bore the "H. Upmann" brand name, but contained cigars from other manufacturers - as brand advertising and a display of craftsmanship. Only after Upmann purchased his own factory in 1844 did the boxes contain H. Upmann cigars produced in-house.

The contemporary significance of cedar-box packaging:

• All top cigar brands use cedar boxes (Cohiba, Davidoff, Romeo y Julieta, Montecristo, and Partagás all continue the practice)
• The aging function of Spanish cedar (adding cedar aroma during cigar aging and enhancing complexity)
• It is an extension of 19th-century gentlemanly luxury packaging aesthetics

Industry consensus: Hermann Dietrich Upmann's contribution to the cigar industry was not only the H. Upmann brand, but also his role as the founder of the global industry standard of "cedar-box packaging".

1862-1893: H. Upmann Wins 7 International Gold Medals in Succession

It is widely circulated in the industry that between 1862 and 1893, H. Upmann won 7 international gold medals in succession. These medals are still printed on cigar boxes today, making it one of the Cuban cigar brands widely recognized in the industry as having the greatest number of gold medals.

Background of the gold medals:

• The late 19th century was the golden age of international industrial expositions (World's Fairs)
• The Paris Exposition, London Exposition, Vienna Exposition, and others all held cigar appreciation competitions
• H. Upmann's consecutive awards reflected international recognition of its craftsmanship
• The designs of these gold medals are still printed on H. Upmann cigar boxes today, serving as historical archives of the brand's visual identity

From the 1860s Onward: The Creation of the Gentleman Gift Market

It is widely circulated in the industry (some historical details are not absolute): H. Upmann began positioning cigars as high-end gifts for banking clients in the 1860s.

The revolutionary nature of this marketing model:

• For the first time, cigars were positioned as "high-end business gifts" (not merely consumer goods)
• Banking clients included German nobility, British industrialists, and American business magnates
• By the late 19th century, H. Upmann had established its high-end positioning in European and American gentlemen's clubs

This gift-market strategy laid an 80-year foundation for the later positioning of "H. Upmann = the cigar of bankers, merchants, and diplomats" - until the Menéndez family went into exile after the 1959 revolution and the H. Upmann factory was nationalized.

The Menéndez Family Acquires H. Upmann in 1937

1937: The company Menéndez, García y Cía, owned by Alonso Menéndez and Pepe García, acquired the H. Upmann factory from J. Frankau SA (also bringing the Montecristo brand into production at this factory).

See montecristo-no2-piramide-deep-dive for the full context of the Menéndez family's acquisition of the H. Upmann factory.

Churchill and the Gentleman-President Bloodline of the Sir Winston Specification

The Naming of the Sir Winston Specification

The naming of the Sir Winston specification is widely recognized in the industry as H. Upmann's gentlemanly tribute to Churchill after the end of World War II.

The Churchill format (ring gauge 47, length 178 mm) was originally a version named by Romeo y Julieta for Churchill in 1946 (see romeo-y-julieta-gentleman-culture) - but industry consensus recognizes that Churchill himself, in addition to Romeo y Julieta, also favored many H. Upmann cigars.

Widely circulated in the industry (some historical details are not absolute):

• H. Upmann lines accounted for a considerable proportion of Churchill's private collection
• The Sir Winston specification in particular is regarded by industry consensus as one of the H. Upmann specifications Churchill smoked most often
• The name Sir Winston directly pays tribute to the knightly title of Sir Winston Churchill

Three Differences Between Sir Winston and Romeo y Julieta Churchills

Differences widely recognized in the industry:

Difference 1: Blend tendency

• Sir Winston: The rounded H. Upmann style, "leather, roasted nuts, dark coffee"
• Romeo y Julieta Churchills: "green foliage, cream, light floral aroma"
• The same Churchill format, but two gentlemanly flavor profiles created by different brand blends

Difference 2: Burn time (consistent)

• The same 47×178 mm specification
• Burns for 75-90 minutes
• Corresponds to the same gentlemen's club time slot (after dinner to midnight)

Difference 3: Market positioning

• Sir Winston: Preferred by bankers and business gentlemen (an extension of H. Upmann's banking-client gift tradition from the 1860s onward)
• Romeo y Julieta Churchills: Preferred by politicians and literary gentlemen (Shakespeare + Churchill's literary temperament)

It is widely recognized in the industry that this difference has not changed for 100 years - the same Churchill format, two brands, two gentlemanly positionings.

February 7, 1961: The Legend of Kennedy's 1,200-Cigar Rush Purchase

Story Background: The Eve of the Embargo Order

H. Upmann has a story widely recognized in the industry as one of the most frequently cited in gentlemen's clubs worldwide - February 7, 1961.

Background:

• President Kennedy was about to sign the comprehensive U.S. embargo order against Cuba
• Kennedy himself was a long-time enthusiast of H. Upmann cigars
• Signing the embargo order meant that the President of the United States would no longer be able to legally possess Cuban cigars

Pierre Salinger's Historic Mission

On the eve of the embargo order signing (the night of February 6 to the morning of February 7, 1961):

• Kennedy dispatched his press secretary Pierre Salinger
• Overnight, Salinger searched Washington, D.C. and purchased 1,200 H. Upmann cigars
• This ensured that Kennedy's private collection would still have ample stock after the embargo

Only after Pierre Salinger successfully completed the 1,200-cigar purchasing mission did Kennedy sign the embargo order the next day.

Widely circulated in the industry:

• Specific specification: Early records identify them as H. Upmann Petit Corona, while Salinger himself later recalled them as "Petit H. Upmann"
• Quantity: 1,200 is widely circulated in the industry, while some versions record 1,000
• Core fact remains consistent: Kennedy rushed to purchase H. Upmann cigars on the eve of signing the embargo order

Three Gentlemen's Club Cultural Meanings of This Story

Meaning 1: A gentleman-president's personal preference can coexist with political decisions

Kennedy signed the embargo order but retained his personal collection - industry consensus regards this as a representative event of the "clear distinction between public and private" principle in 200 years of gentlemen's club culture:

• Public decision: Signing the embargo order based on national interests
• Private preference: Retaining a personal cigar collection
• The two do not conflict - a gentleman does not use policy to force himself to give up personal taste

Meaning 2: H. Upmann's status among modern gentleman-presidents

After the 1961 event, it became widely recognized in the industry that:

• H. Upmann became a "gentleman's sacred object under embargo" in American gentleman circles
• Industry consensus holds that "owning 1959-1962 H. Upmann Pre-Embargo means owning Kennedy's gentleman bloodline"
• Pre-Embargo H. Upmann remains one of the most sought-after categories of vintage cigars at auction houses more than 60 years later

Meaning 3: The special status of the Sir Winston specification

In this story, it is widely circulated in the industry (some details are not absolute) that the Sir Winston specification was also one of the formats with the highest share in Kennedy's final batches of private collection.

Although the main focus of Salinger's 1,200-cigar purchase was Petit Corona / Petit H. Upmann, the industry believes that the Sir Winston specification also accounted for an important proportion of Kennedy's overall private collection.

The Contemporary Extension of the Gentleman-President Cigar Lineage

Sir Winston Connects 183 Years of Gentleman-President Bloodline

The Sir Winston specification is widely recognized in the industry as connecting the complete lineage of gentleman-president culture:

• Late 19th century: The commercial-class gentleman of German banker Hermann Dietrich Upmann
• Mid-20th century: Churchill's statesman gentleman (Prime Minister, Nobel Prize in Literature, British nobility)
• Mid-to-late 20th century: Kennedy's presidential gentleman (35th President of the United States, rush purchase before signing the embargo order in 1961)
• 21st century: Top Asian gentlemen among the gentlemen's club members of the contemporary W Cigar Bar Da'an flagship store

Sir Winston is regarded by industry consensus as the "unchanged gentlemanly standard across three generations".

Three Characteristics of Asia-Pacific Gentleman-President Culture

The contemporary extension of gentleman-president culture in the Asia-Pacific region is widely recognized in the industry:

Characteristic 1: The H. Upmann collection combination of top Asia-Pacific gentlemen

H. Upmann specifications preferred by industry consensus:

• Sir Winston (Churchill specification) - the gentleman-president canon
• H. Upmann Magnum 50 (50×160 mm)
• H. Upmann Magnum 54 (54×120 mm)
• Connoisseur No.1 (48×127 mm)
• Sir Winston Gran Reserva (launched in 2017, specially aged tobacco harvested in 2011)

These 5 specifications are jointly regarded as the "H. Upmann collection combination of top Asia-Pacific gentlemen".

Characteristic 2: Emphasis on "gentlemanly judgment" rather than "political power"

The Asian version of gentleman-president cigar culture is widely recognized in the industry as no longer emphasizing "political power", but instead emphasizing "gentlemanly judgment":

• The ability to maintain gentlemanly composure during important decisions
• Personal boundaries with a clear distinction between public and private
• Patience in long-term investment decisions
• A perspective for horizontal exchange with global gentlemen

Characteristic 3: The status of Sir Winston at W Cigar Bar Da'an flagship store

Sir Winston is widely recognized in the industry as one of the H. Upmann specifications most popular among gentlemen's club members in the inventory of the 33 VIP cigar lockers at W Cigar Bar Da'an flagship store (24-hour constant-temperature aging, professional 70% / 18°C environment, dedicated maintenance).

Sir Winston Gran Reserva: The Historical Continuation of a Contemporary Flagship

The Historic 2017 Release

2017: H. Upmann launched the first Sir Winston Gran Reserva:

• Tobacco harvested in 2011 (top production area of Vuelta Abajo San Juan y Martínez)
• Released in 2017 after 6 years of deep aging
• Limited release, numbered at the factory
• Widely recognized in the industry as the pinnacle of contemporary H. Upmann collecting

The Status of the Gran Reserva Series in the Habanos S.A. System

The Gran Reserva series is regarded by industry consensus as the highest-echelon aged series under Habanos S.A.:

• Only a very small number of specifications from each brand receive Gran Reserva treatment
• Mandatory deep aging of tobacco leaves for more than 5 years
• Limited release
• Sought after by collectors

Cigar specifications that have received Gran Reserva treatment:

• Cohiba Behike BHK series (specific-year Gran Reserva)
• Partagás Lusitanias Gran Reserva 2007
• Romeo y Julieta Wide Churchills Gran Reserva
• Montecristo No.2 Gran Reserva (limited years)
• H. Upmann Sir Winston Gran Reserva 2017 - the official coronation of a 70+ year gentleman-president bloodline

Appreciation Characteristics of Sir Winston Gran Reserva

Widely recognized appreciation characteristics of Sir Winston Gran Reserva:

• Tobacco harvested in 2011, released in 2017 after 6 years of deep aging
• Widely recognized in the industry that the blend is consistent with standard Sir Winston, but the flavor is more rounded
• Deeper leather layers and more evident sweetness in the later stage
• Long finish and high complexity

For gentlemen's club members, Sir Winston Gran Reserva is regarded by industry consensus as a "single-specification flagship suited to the most important commemorative moments" - not for everyday appreciation, but a "ceremonial moment paying tribute to 183 years of gentleman-president cigar lineage".

The Advanced H. Upmann Appreciation Path for Gentlemen's Club Members

For gentlemen who want to experience the complete gentleman-president cigar lineage, the advanced appreciation path widely recognized in the industry is:

Stage 1: H. Upmann Style Baseline

H. Upmann Magnum 50 or Connoisseur No.1

• Experience the medium strength and rounded foundation of the H. Upmann style
• Establish an understanding of H. Upmann flavor

Stage 2: Entry into the Gentleman-President Bloodline

Standard Sir Winston specification (47×178 mm Churchill)

• Experience the gentleman-president bloodline of the Churchill format under the H. Upmann blend
• Compare with Romeo y Julieta Churchills and experience the differences between the two brands
• 75-90 minutes of gentlemen's club appreciation time

Stage 3: Contemporary Flagship

Sir Winston Gran Reserva 2017

• A rounded version after 6 years of deep aging
• Reserved for important commemorative moments in life
• Paired with 25-year single-cask Scotch whisky

Stage 4: Historical Archive Grade (if obtainable)

Pre-Embargo H. Upmann (1959-1962 three-year window)

• Regarded by industry consensus as a flagship collectible with a complete paper trail
• Final production before Kennedy signed the embargo order in 1961
• Auction value can reach several thousand USD / stick
• It is the highest-echelon collection for contemporary gentlemen's club members

Pairing suggestions:

• Single-cask Scotch whisky aged 25 years or more (Macallan 25, Highland Park 25)
• Or Cognac VSOP / XO (Hennessy Paradis, Rémy Martin Louis XIII)
• Recreate the Kennedy / Churchill gentleman-president ritual widely recognized in the industry

Conclusion

H. Upmann Sir Winston is widely recognized in the industry through a 180-year gentlemen's club consensus:

A gentleman-president is not a title, but judgment.

This sentence condenses the core spirit of H. Upmann's 183-year brand history:

• 1843 Hermann Dietrich Upmann arrives in Havana - gentlemanly judgment from a banker's perspective
• 1844 invention of cedar-box packaging - judgment in gentlemanly luxury aesthetics
• 1862-1893 winning 7 international gold medals in succession - judgment in craft quality
• 1937 Menéndez, García y Cía acquires the H. Upmann factory - judgment in business strategy
• Post-World War II naming of the Sir Winston specification - gentlemanly judgment paying tribute to Churchill
• 1961 Kennedy's rush purchase of 1,200 cigars before signing the embargo order - gentlemanly judgment with a clear distinction between public and private
• 2017 release of Sir Winston Gran Reserva - the contemporary coronation of the gentleman-president bloodline
• 2026 W Cigar Bar Da'an flagship store's 33 VIP cigar lockers and Sir Winston collection - the continuation of judgment among Asian gentlemen's club members

For gentlemen's club members of W Cigar Bar, collecting H. Upmann Sir Winston is not only possessing a top Cuban cigar, but also possessing 183 years of complete gentlemanly judgment lineage from a Bremen banker to the Washington White House to Taipei's Da'an District.

When you light a Sir Winston, you are not merely smoking a Churchill specification. You are taking part in a 183-year river of gentleman-president culture, from Hermann Dietrich Upmann's cedar box, to Churchill's speeches in the House of Commons, to the final 1,200 cigars before Kennedy signed the embargo order, and on to today's top Asian gentlemen.

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Source of inventory: Cuban cigars from four major authorized channels (PCC authorized dealers, official Cuban state-run stores, Swiss general distributor, Spanish general distributor). W Cigar Bar Gentlemen's Cigar Lounge - Taipei Da'an District - complete H. Upmann series: Línea Habana / Magnum / Connoisseur / Sir Winston / Sir Winston Gran Reserva 2017 / Edición Limitada / Pre-Embargo vintage collection (if obtainable).

LUBINSKI Italy accessories general distributor - cigar bistro - Da'an flagship store with 33 VIP cigar lockers (24-hour aging - professional 70% / 18°C aging) dedicated maintenance - founding store of the Capadura cigar brand.

Cigar Prince Wilson Tsai personally plans the advanced H. Upmann path for VIP clients - from the entry-level Magnum 50 to the flagship-level Sir Winston Gran Reserva 2017, including Pre-Embargo vintage collection appreciation.

Venue information: https://share.google/d9NIeFEetij9qWKj0

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

This site is for adults aged 20 and above only. Smoking is harmful to health. Smoking cessation hotline: 0800-636363.

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