And so we end where we really should have begun: with the H. Upmann Connoisseur No. 1.

Many moons ago when I began my Upmann chronicles I lamented my inability to find a Connie 1. As the cigar you most often hear talked about by cigar aficionados, I think of it as the consensus building Upmann, and presumed that were I to run a simple query of the holdings of the members of the cigar encyclopaedia I edit, the Connie 1 would be by far the most widely held Upmann. As it turns out however, I was mistaken: the honour goes to the H. Upmann Half Corona (at 8^th overall), followed closely by the Magnum 46 (9^th); even the Royal Robusto (22^nd), an exotic cigar, outranks the humble Connie 1 (25^th).

I didn’t seek the Connie 1 out after that first fateful day, content to run with what I had and keep the mediocre Petite Corona (a miserable 81^st) as my comparison point, but as it turned out a Connie 1 found me. I was at a herf, a small gathering of friends and brothers in the leaf when, as often happens at these events, everyone started handing out cigars. I’m not sure who handed this one to me, but whoever you are: thank you. The afternoon is sunny and I’m in the courtyard with a friend, a few beers and a mostly full bottle of mid-range blended scotch, an environment where the Connie 1 is sure to thrive.

The cigar is a little hot on the light, and feels a bit dry. I neglected to give this one a rinse before smoking, which I think might have helped it. I puff enough to make sure it’s fully lit, and then let it sit awhile. When I return the cigar has mellowed out to a light tobacco with barnyard notes and a herbal tang.  At this early stage it has all the makings of a very pleasant casual smoke.

The whisky of the day is Johnny Walker Gold Label, a drop I’ve had both more and less than my fair share of over the years. In Japan Gold costs less than Black Label does in Australia, and I used to drink a ton of the stuff in the time I lived there. My apartment in China had a feature wall that was boldly decorated with a swirling pattern of red paint and gold leaf, and to complement it I maintained a bar of only red and gold labelled bottles, in which Johnny Gold figured heavily. It’s not a great scotch, but it is a very easy scotch: not very challenging, but it goes down quietly. A little like the Connie 1, come to think of it.

In Australia Gold Label is too expensive to buy casually. If I want a nice scotch then my coin is better spent on an interesting single malt, and if I want to put scotch inside of my coke at the movies then the Red Label will do just fine. On rare occasion though I will bring a bottle back through duty free, and it was such a bottle that many years ago figured in the crime.

Throughout my teens and early twenties, I was blessed with the two key elements for the youthful party host: a large house and parents who went away a lot. I’ve never quite understood my parents’ thinking in their renovation schemes; they are barely drinkers, and have little interest in entertaining. Over the thirty years they’ve owned their home I can think of maybe five occasions when they hosted a gathering of more than ten people there, and yet, over the years they have consistently and methodically renovated a ramshackle, pokey mess of a place into a party palace. The house today has huge, open rooms, two big enough for dance floors, and a large billiard room complete with a bar, wood panelling, and bench seats set into the walls. The big rooms are at the back of the house, far from the street and the neighbours’ bedrooms, so nobody ever complains about the noise. At the front of the house there are many small nooks, intimate spaces with couches and beds where people can slip away to. Outside there is a big area with tables that can be covered in summer and heated in winter. There is a spa for goodness sake! Suffice to say, the bacchanals of my late teens were legendary.

I was about twenty two on the night of the crime, and was burning the party card pretty hard, throwing at least ten a year. Perhaps because of this, enthusiasm for my elaborate themes was waning, and attendance had dropped considerably from the days when I could expect at least a hundred guests at any bash I threw. The night in question was in the middle of winter, cold and wet, and just sixteen guests showed up, all of them close friends. I had recently returned from Singapore, and so my already substantial bar had been bolstered by the booty of duty free, one bottle of Glenfiddich 21, and my first ever bottle of Johnny Walker Gold. I stashed the whisky in the oven, my traditional hiding place for the good stuff, the theory being that I could point those I considered worthy in the right direction, but that the hoi polloi could content themselves with the plentiful cheap booze that had been laid out, and not pour my $100 scotch into their glasses of coke. By the night in question the scheme was compromised somewhat as most of my intimates already knew about the hiding place, but I didn’t fret it: “once worthy, forever worthy” I decreed.

Like most good parties, my memory of the morning after is clearer than the night before. I was going about my usual ritual, collecting the bottles that were scattered around my house, when I came upon the first offence: the bottle of Glenfiddich 21 on the floor in the library, half empty. I snorted in disgust at the presumption, but let it go. A little while later I was in the billiard room where, on the bar, I discovered a far greater crime. My father had, years before, inherited a large collection of old wine from my great uncle. It had been kept without much care in a damp garage, and much of it had spoiled, but he had hung onto a few bottles anyway, including the bottle of 1970 Penfold’s Grange that now sat, open on the bar. It was two thirds full, and the remains of the cork were floating on the top of the liquid, having been pushed into the bottle. I sniffed it: pure vinegar. I was sure my father would never notice – to him they were just a few old, mouldy bottles, but still… the presumption! The final crime I didn’t discover until the clean-up was complete: the bottle of Johnny Gold, unopened at the start of the evening, was gone. No empty bottle. No box. Nothing. A straight up abduction.

That afternoon I fired off a furious email to the sixteen attendees, outlining the offences. Eight replied with denials. There were no confessions. Had it been one of my regular bacchanals I wouldn’t have given it a second thought, but this was not: each of the sixteen guests was an intimate friend, and many of them remain so. Over the intervening decade I have eyed every bottle of Johnny Gold that they have produced with great suspicion, but I am still no closer to an answer than I was that first morning; the thief, the vandal, the wolf: they walk among us still!

My friend catches me inspecting the bottle of Johnny Gold he has brought for us, looking for a mark that would indicate its date of manufacture, and knowing the story well, he winks at me. “Nah mate,” he says, “I filed off the VIN.”

The Connoisseur No. 1 ends extremely well with no tar and a lighter tobacco note than it has had at any point before. It’s not the richest smoke in the world, but it isn’t supposed to be, and is fantastic for it. I always smoke faster when I’m talking, and I demolished this one in less than 45 minutes. Generally the faster you smoke a cigar the hotter it burns and the worse it is, but this one did not suffer at all for the brevity; it was better, say, than the 160^th Anniversary version of the same thing that took me at least twice as long. A great, business like smoke. Better than the Petite Coronas.

H. Upmann Connoisseur No. 1 on the Cuban Cigar Website.

And so we come to the Sir Winston.

There are only about six famous cigar smokers in history (seven if you count Bill Clinton, although his tobacco habit is more infamous than famous), and of them none more so than Sir Winston Churchill.

Cuba’s contribution to the Second World War involved the sinking of one U-Boat, the execution of one bumbling spy, arming Ernest Hemmingway’s fishing sloop and, most importantly, sending the British Prime Minister case upon case of cigars. The most famous is Romeo y Julieta, but almost every factory offered Churchill a similar deal: an unlimited supply of gratis custom cigars as a small token of thanks to the leader of the free world. After the war many of these brands released Churchill’s customs to the general public, and at one time Romeo, Bolivar, Hoyo de Monterrey, Saint Luis Rey, Partagás, Punch and H. Upmann all had a cigar named after him, and the Julieta No. 2, the vitola that he preferred, and of which nearly every marque has a representative, became forever known as the Churchill.

All of which seems a bit excessive to me, as by all accounts he smoked ten cigars a day and dipped them all in cognac, a perfectly good way to ruin any nuance that fine tobacco might possess.

The H. Upmann Sir Winston is the flagship of the Upmann line. It comes in a substantial box, especially designed for aging, and commands a higher price than its colleagues for its allegedly superior tobacco. This particular example is about fifteen years old: not quite the twenty that the Min Ron Nee encyclopaedia recommends for the cigar to reveal its full character, but well beyond the minimum eight.

The cigar begins badly: for the first few puffs it is bitter, the sting of my botched light leaving it hot with a chemical note. Once the initial heat fades I would expect an Upmann this old, especially a Sir Winston, to become mild, but it doesn’t at all. Once it settles down it is dark and brooding, medium strength tobacco and earth notes. Strong coffee. Cocoa. Floral on the aftertaste. Fantastic.

There’s an olive grove that sits on a hill an hour or so out of Melbourne, and I am vaguely acquainted with its owner, Samwise. He’s seventy five or so now, with three divorces and two strokes under his belt, and his faculties aren’t what they used to be. His estate is large and very beautiful, with the long, straight lines of the groves sweeping down from the house to the lake far below, and he rules it like something of a demented king. Once I enquired about the trap on his porch, a steel cage big enough for a lion, baited with a hefty chunk of steak. “It’s for the neighbour’s cat” he told me. “If I catch him I will shoot him.”

Samwise is a true epicurean, who maintains a full bar, a comprehensive wine cellar, and can casually throw together a feast in a matter of minutes, but it is in his humidor that our interests primarily intersect. I have great fondness of our time together, long evenings looking out over the valley with the leaf, him sharing the tales of his lifetime of adventures, and me sharing mine of the imprudence of youth. It is bittersweet, however, as his decline is plainly visible: his stories ramble or trail off, or repeat themselves, and sometimes his jokes don’t make a lot of sense.

There is, however, one sure fire way to get old Samwise back to the top of his game: introduce the scent of a woman.

At the mid-point the cigar has weakened, light herbaceous tobacco with an aromatic, hoppy aftertaste. It is very pleasant.

Samwise is always at his best around women, if your version of best is a quick witted, flirtatious letch. Once I watched him spruiking his olive oil at a farmer’s market, proclaiming it as the oil of a thousand uses. A middle aged woman enquired as to what they might be, and when she looked put off by his first suggestion of “massage oil” he simply winked and said “well, if you don’t like that one I’d better not tell you the rest.”

My favourite moment came as we enjoyed some cigars (for the sake of cohesiveness let’s say they were Sir Winstons) outside a café in town. The waitress was in her early twenties, blonde haired and blue eyed, with that freshly scrubbed country charm. “That smells great,” she said, as she cleared away our coffee cups. “Is it a good one?” Samwise grinned. “Yes, yes, it’s the best” he said. “I got it from Bill Clinton.” The smile falling from his face, he looked at her intently. “Would you like to try it?”

The girl turned beet red, and giggled nervously, and stood before us for fifteen seconds or so. Searching for a retort but not finding one, she turned and went back inside, giggle all the way. I congratulated Samwise on his joke, and he looked at me seriously. “Did you see her reaction?” he said. “I think she is in love with me.” A guy brought out our cheque.

Throughout the last half the cigar has been growing steadily thicker, and with a third left it has a heavy, smoky note that borders on tar. It feels a little ridiculous to say that a burning leaf tastes like smoke, and then to opine that one kind of smoke is superior to another, but that’s exactly what I propose to do. This is smoky in the same way that Highland scotch is smoky: there is a hint of charcoal, of iodine, and of long dead monsters. It is an acquired taste, but I have acquired it. It does not taste like a tire fire.

In the last inch or so it does begin to taste like a tire fire: it is bitter, with ash and tar, although not unreasonably so for a two and a half hour cigar. The lingering aftertaste is straw and oats. It is notable that I have had two cold beers in my bag this entire time, and never felt a need to touch them.

The real cigar to compare this one to is not the H. Upmann Petite Coronas, but rather the Romeo y Julieta Churchills that I smoked last year. Both cigars are exactly the same size and of a similar vintage, have been kept in similar conditions, and were combusted in a similar way. The difference between them, however, is night and day. Where the Romeo was bland and papery, the Sir Winston is punchy, rich, and anything but tasteless. The Upmann wins.

H. Upmann Sir Winston. Lives up to the hype.

H. Upmann Sir Winston on the Cuban Cigar Website