The Old Glory Society is a gentlemen’s cigar club that exists, not only in the physical world, but in your mind. In the Society’s formative years, I served as lead propagandist and I still write words about cigars and the groovy, historic vibe that surrounds them under the Society’s sacred banner.

Cigar Salutations From The Old Glory Society

Today’s lesson, my leaf-toking brethren is about two gentlemen you may have, quite literally, had your lips around recently. The dudes of whom I speak are Henry Clay and Simon Bolivar. Today, each has his name wrapped around various tobacco concoctions, but in their day, both of these cigar idols were potent political moguls and leaders of men.

Clay, born in ol’ Virginny in 1777, was a key figure in American politics for a good portion on the 19th century. They called him the Great Compromiser and he was a staunch advocate for the emerging Western territories, served in both the Senate and The House, devised the Missouri Compromise and ran for president twice—twenty years apart. All in all, he was a legendary American, and as it was a sign of great affection and respect back in the day, a cigar brand was named after him. The signature Henry Clay brand we know today is typically a Dominican-made cigar with a simple band that bears the man’s name. It’s nothing fancy, in fact by some measure, it’s pretty rough, packaged in box-pressed bundles with a no-nonsense construction and, often, leaf stems clearly visible. The smoke is hard-charging, leaning toward harsh and it produces a dark gray mottled ash, like the dappled gray gelding that runs at Santa Anita. Like the man, what you see is what you get, and I’ve smoked thousands of them. Relatively cheap and very consistent, I think you should have a box in your humidor at all times, the perfect cigar for occasions that aren’t special. (I write extensively about Henry Clay in my upcoming book, Leaf of Liberty, The American Cigar Story.)

Simon Bolivar is a Venezuelan, born in 1783. He is generally considered one of the most important, profound voices in the struggle against Spanish authority in what became known as the Bolivarian countries (Venezuela, Colombia, Ecuador, Peru and Bolivia). They called him The Liberator and he was a respected intellectual and an influential military and political figure. No single person did more to promote freedom and independence in South America than Bolivar. There are now cigars from the Dominican and elsewhere that bear the Bolivar name, but the flagship Bolivars are from Cuba. They feature a wonderful cigar band with a uniformed Bolivar and the cigars themselves are simply some of the best in the world. I prefer the Belicosos Finos, but the Royal Coronas and Petit Coronas are excellent as well. I find the experience just a bit south of full bodied with a refined gray ash, and I like to fill the room with smoke and bath in the purple-white cloud and think back to a time when real men had countries, and cigars, named after them.