Trinidad is a name that will forever be associated with the legendary “diplomatic” cigar that Fidel Castro bequeathed to lucky statesmen visiting Cuba. It was considered by many to be the most exclusive and presumably the finest cigar of its time. So it came as a surprise when Castro revealed to Marvin Shanken in a Cigar Aficionado interview that he never offered the Trinidad brand to visiting dignitaries — he always presented them Cohibas. In fact, he even denies knowing about the Trinidad brand in that sense.

Perhaps, just perhaps, there is a reason for that.

The Trinidad 100th Anniversary line was created by Altadis USA to celebrate the founding of the brand by Diego and Ramon Trinidad around 1905. The Trinidad brothers were originally hardware traders who bought their wares in the city of Santa Clara, Cuba, and then transported them for sale to the remote villages of the region. One day they were hauling their empty wagons back to Santa Clara to resupply and they noticed the magnificent tobacco crops of the Pinar del Rio around them. It occurred to them that they might as well fill their wagons and try to sell some of this commodity in Santa Clara when they got there. They did this, and subsequently found themselves in the tobacco business. But eventually they noticed that there was an even greater profit to be had in the final product, cigars. They hired a number of cigar rollers and set up shop in the nearby town of Ranchuelo. The Trinidad y Hermano brand was born.

The business continued to grow and the brothers hired more workers and moved to larger factories. The company was thriving until it was beset by what seemed at first to be a disaster: a large crop of tobacco leaf destined for cigars was attacked by the fearsome tobacco beetle. All seemed lost, so Diego ordered that the remains be chopped up and salvaged for cigarettes. But instead of a loss this turned out to be a windfall. They saw their profits double, and the cigar factory quickly became a cigarette factory.

And while they continued to make cigars, the Trinidads were primarily cigarette producers. By the 1950’s, Diego’s American-educated son, Diego Jr., had refitted and modernized the Trinidad factory into what Cuba’s weekly Bohemia called “An Industrial Giant of Cuba.” In 1959 their earnings were in excess of one million U.S. dollars. But within a few years this wealth and power would fall prey to the treachery of Fidel Castro in a very personal way.

Diego Trinidad was opposed to the Batista government which had seized power in 1952. Batista was a dictator of the first order, and Trinidad saw that if he was overthrown democracy might return to Cuba. This would be good for both Cuba, and his business. Fidel Castro’s revolution presented an opportunity for a return to democracy, the progressive constitution of 1940, and a better life. There was no indication at this point that Castro would seize power for himself and socialize the country’s industries. Documents exist that show Trinidad was approached by Castro for funding, and he thereafter made sizable contributions to Castro’s movement. In part this was to promote safe delivery of cigarettes through hostile territory in the countryside, but in part it had to be because he had faith in the movement. If only Trinidad had known that Castro’s victory would destroy private industry and rob him of his livelihood, he would no doubt have done differently.

So one wonders what goes through Castro’s mind when he hears the name Trinidad. Maybe there’s a very good reason why he denies knowledge of the name of this legendary cigar. It’s pure speculation on my part, but perhaps acknowledgement of a friendship betrayed — especially in the name of the world’s finest cigar — just doesn’t sit well with him.

The Trinidad Anniversary cigar celebrates one hundred years of struggles and success on the part of the Trinidad family. Altadis, who now owns the brand, appears to have released very few of these and I feel privileged to happen upon a few. Data on the release date and number of cigars produced is lacking, but we do know the nature of the blend: a Nicaraguan corojo wrapper, Connecticut broadleaf binder, and filler from Nicaragua, Peru and the Dominican Republic.

Upon first examination I thought there was something wrong with the head of this cigar. It looked like there was some stray tobacco caked or pasted on the cap, so I picked at it a little and to my surprise up popped a thin little pig tail! It was crushed down on top the head so completely that I didn’t even see it when I took the photo above. This, along with a quadruple cap, was my first indication that this was a finely constructed cigar.

The wrapper is an oily, darkish natural color with a little bit of tooth. Prelight the scent was a little grassy, but otherwise unremarkable. A somewhat difficult cut and an easy light later I was greeted with the sweet smell of corojo and gobs of smooth cool smoke. The first half of this cigar is perfectly balanced between sweet caramel flavors and a slightly salty cedar. The draw is a little on the tight side, but accommodating enough to bring a nice tasty cloud with each pull. The burn is even and trouble free, while the ash that builds is a solid white trophy that I proudly display to the dog. The dog is not impressed. I am.

Into the second third the body builds from an easy medium to something approaching full. The flavor wanders into the vicinity of cocoa, backtracks to leather, and then reminds me again of the salty cedar from the start. The last third develops a peppery core on the tongue while caramel and cocoa continue their jig in my nose. At this point I am almost ready to call this robusto “Pepinesque,” but it lacks the horsepower. The finish lengthens and the aftertaste grows spicier, while the smoke remains smooth to the end, departing with a sharp tang as it waves goodbye.

Take a look around your B&Ms for this one. It’s not much more expensive than the regular line Trinidads — around 8 or 10 bucks a pop — but in my opinion it’s light years better. It’s not as full bodied as the standard line, so if that’s what you’re expecting look elsewhere. But if you like a solid medium bodied cigar with a lot of complexity and classic corojo flavors, you won’t regret picking up a few. If you can find them.