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Big Boss is one of the most iconic video game characters for his duel role as a hero and a sympathetic villain. With Metal Gear Solid: Ground Zeroes and The Phantom Pain on the horizon, gamers are excited to once again take on the role of the legendary soldier. Yet one thing some gamers have always wondered is, what cigar does Big Boss smoke?

Many have asked this question on message boards but have received no clear answer. Most people have just listed common cigars followed by a discussion about what cigarette Solid Snake smokes, and after that, everyone just gives up. Someone has even asked this question on Answers.com to no avail.

Besides being an avid gamer (also a Metal Gear fan) who has written about video game culture, I’m also an avid cigar smoker and a cigar critic in the Bay Area. I’ve had the opportunity to sample a verity of premium cigars, meet respected people in the cigar industry, and blog for the Campbell Cigar Club.

To answer this great cigar riddle, I visually examined the cigar Big Boss smokes in the beginning of Metal Gear Solid 3: Snake Eater and then compared and crossmatched it with other cigars. The one Big Boss is smoking has the following details:

It has a pyramid figure (often mistaken for a torpedo figure)

It has a mild to full-bodied strength (based on the cigar’s texture)

It’s of Cuban origin

The cigar brand Habano (a reference to the Cuban state tobacco company Habanos S.A.) is obviously fictitious. However, given the small number of details and hidden content in the series, the cigar has to be inspired by a real brand.

I have speculate that the cigar was inspired by the H. Upmann No. 2, along with the Montecristo No. 2. Both brands are among the most popular and sought after Cuban cigars, and they’re almost identical. Besides a pyramid figure and identical ring gauge, the two cigars also share a similarly designed cigar band. They’re also well known for having a smooth draw along with a cream and cedar flavor.

It’s no accident that the cigar Big Boss is smoking is inspired by an H. Upmann as it was also the favorite cigar of President John F. Kennedy. A day before authorizing the trade embargo against Cuba, President Kennedy had Pierre Salinger, the White House press secretary, acquire 1,200 H. Upmanns. The Kennedy administration is also credited with establishing the modern Special Forces to combat the rise of communist insurgences in Asia and Latin America.

With the historical context — along with his background in the Special Forces and being a protege of The Boss — it could be speculated that Big Boss was given a few H. Upmann No. 2s as a gift from President Kennedy.

This is, however, not the same cigar that he is smoking in Metal Gear Solid 4: Guns of the Patriots and Metal Gear Solid V: The Phantom Pain. Despite several good opportunities to examine the cigar band, I was unable to identify or guess the last cigar Big Boss smoked in Guns of the Patriots. I was able to identify the cigar smoked in The Phantom Pain, though. After closely examining the cigar featured in trailers and previews from the Electronic Entertainment Expo, it’s obviously a generic Cohiba based on the yellow, white, and black decor of the cigar band.

All these conclusions are based on the details presented and critically analyzed using my knowledge of premium cigars. Other gamers who also have a rich knowledge on cigars are welcome to offer their own hypothesis on what cigar Big Boss smokes.