Smoking a cigar that is formed into a whimsical shape, or adorned in some unique fashion is not an experience that is meant for the masses. There's a reason why most of the cars you see on the road are different shades of the same color, and the same is true for the cigar-smoking community.
According to Premium Cigar Association (PCA) Retailer Member Survey Results for 2024, the standard parejo vitola commonly known as the toro continues its reign as the most popular stogie size accounting for 79% of all cigar sales at brick-and-mortar retailers. Take a look at the Klaro portfolio, and you will find that the vast majority of the cigars that we stock mirror these statistics. Not because we personally prefer to puff on a toro, but because it's what people want for whatever reason. At least as of late...
Personally, I find the toro vitola to be incredibly unexciting. Especially since I know that anything of a significantly smaller or larger ring-gauge has the potential to provide a vastly different smoking experience, and in many cases, a twist on the flavors and aromatics detected. Even more enticing to me is the mighty figurado cigar vitola, which has long been lauded for its ability to enhance smoking sensations, as well as the taste bud tantalizing attributes of various premium cigar blends.
Oscar Valladares knows this better than anyone and continues to roll some of the most creative cigars on the market today. And while the Honduran boutique cigar brand does still produce a ton of toros every year, it's just a means to an end, with the goal being the ability to produce some really wacky stogies for those of us who truly don't give a shit about smoking the same shaped cigar as everyone else at the local lounge.
Let's take a look at the Island Jim Connecticut No. 2 by Oscar Valladares for a moment, and hopefully, it will help determine whether or not stepping outside the cigar-rolling norm is truly beneficial, or pure tomfoolery.
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Unlit Impressions
The first time I saw someone smoking a pencil, pretending that it was a cigar, it was the incorrigible "Albert the Alligator" from Walt Kelly's Pogo comic strip. Something about the image of that stogie-smoking reptile stuck with me, and for the better part of my life I have pined for the chance to spark a pencil and puff away in earnest.
So when I learned that there was a cigar with a Connecticut wrapper serving as the yellow-painted pencil sides, a scrap of maduro for the tapered wooden shavings on the shoulder, and some reddish mystery leaf representing the lead tip, I knew that my adolescent dream of someday smoking a pencil was finally within reach. Oh, and let's not forget that shaggy foot, which doubles as the eraser section of the pencil, and makes for a wonderful open-ended aromatic accent.
What sort of smells could these be, you ask? How about piping hot cinnamon rolls fresh out of the oven, glazed in sweet cream icing, and served atop a cedar cutting board? Wrapper aromas might produce more of a mellow milk and honey-drenched moment of contemplation, but at least it isn't a total hay and dried toast smell like many of these varietals tend to favor.
Cold draws can only be pulled once the "lead" of the pencil has been removed, and then they unravel with a cedar-strong, nutmeg, and clove taste that gradually grows into a similar cinnamon roll flavor profile.
Cigar band fans may enjoy the caricature of Mr. Jim Robinson himself on the band, but I personally find it a bit overly glossed, and with the gold trimming it becomes damn near impossible to photograph without glare. Cigar review woes run rampant some days, I swear...
Initial Smoke
Like an unsuspecting gringo going half a chip too deep into a seemingly harmless bowl of salsa verde, the combustion of this blend's shaggy "eraser" catches me off guard once again. Spicy, resinous, and unrelenting, the intensity continues until the wrapper is reached and starts to sizzle. What emerges at this moment is an aromatic incense-like experience that does not last long, and makes you wonder what the hell you've gotten yourself into before going creamy cashew and almond all of the sudden.
1st Half
The "island" side of this premium cigar blend wastes little time in letting its presence become known, with the creamy texture and mild milkiness of coconut erasing all thought of initial impressions. Cashews and almonds manage to hang on though, and with the taste of cedar and cinnamon swaddling the tongue, a unique spice note develops. It's not clear as to what kind of tobacco strains are layered inside this version of the Island Jim line, but I wouldn't be the least bit surprised to find a pinch of Sumatran leaf in there somewhere.
Medium everywhere but in strength, spiced berry tea and touches of cedar send retrohales skyward. Elevated aromatics leave a lingering dark fruit jam taste upon the taste buds, along with the slightest hint of honey and dried hay. Shortbread cookies and saucers of cream come to mind and then refuse to leave, clearing the way for what will soon be one of the milkiest cigar second halves money can buy.
2nd Half
Even though cedar-powered retrohales grow gradually more intense and spicy, the milk-and-honey mixture on the palate smooths over most of the sharper edges. Sweet, satiny, and very much vanilla ice cream at moments, this section of the cigar is its simplest and smoothest moment. The only thing about the blend that maintains medium status is the body, as even the spicier scents on retrohale temporarily fizzle and turn cedar sappy and suave.
This is the "point" in the cigar where Connecticut Shade-Grown blend enthusiasts will surely start squirming in their seats. Although I personally find the majority of this portion of the barrel of the cigar to be a tad too tame for my personal taste, I cannot deny how clean and creamy it becomes. All of those subtle baking spice notes and hot milk spiked with honey are exquisitely implemented, and with the Spanish cedar still lingering in the background it all makes for a most magical smoking sensation.
Parting Puffs
Oh, how I do love it when a premium cigar blend transitions into parting puffs with an organized plan of action, and a damn delicious one to boot. For the Oscar Valladares Island Jim Connecticut No. 2, that means taking all that milky magic I just described and then serving it to you with a piping hot plate of cinnamon rolls. This resurrection of flavor profiles from the start of the stick is astoundingly scrumptious, and with the creaminess of the smoke's texture levels reaching maximum levels, I cannot think of a more appropriate way to finish off this blend.
Clean and focused on a mellow mixture, the last minute or two of this cigar reminds you of its wrapper leaf's roots, as stray flavors of South American cedar and rainforest soil mix within the folds of heavily fermented tobacco tastes. Brilliant.
The only moment of unpleasantness was when a random touch of under-fermented leaf hit the tongue, which luckily did not last too long, and was not too astringent or ammonia-heavy.
Ash / Burn / Smoke / Draw
Another badass burner from Oscar Valladares. As long as you are properly storing and dry-boxing your cigars, you have nothing to worry about when it comes to the construction and combustion of this blend. Just be wary when lighting that shaggy foot, as this style of cigar aesthetic is notorious for sending scraps of ash everywhere if you aren't careful.
Final Thoughts
I have, and will continue to, smoke and savor anything with the name "Island Jim" on it just as long as it is produced by Oscar Valladares. Each one of the blends in this line brings something unique to the table, with this Connecticut version being the most milky and at moments, mild.
While my personal smoking preferences push me toward bolder, darker blends 90% of the time, I do dearly love a good Connecticut Shade smoke when the mood strikes me. Especially when it has a fair deal of backbone and a mixture of spice and cedar upon retrohale.
But perhaps the primary reason why I adore this cigar is because it reminds me of one of my cigar-smoking heroes: Albert the Alligator. The creature that made me laugh out loud when I saw him sparking a No. 2 pencil in a random comic strip, as he had burned through the entirety of his cigar box and had nothing left to spark save for what was tucked behind his ear.
Listen to me. Here I am rambling on about alligators having ears. Take a break from your boring-ass toro routine and buy a box of this boutique blend instead. You might just find that puffing a pencil for a change and smoking outside the box is more fun than you could ever have imagined...
Flavor, Aroma & Transitions
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Depth & Complexity
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Construction, Burn & Physical Appeal
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Backstory & Branding
Overall Balance & Repeatability
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Stogie Specs
Cigar |
Oscar Valladares "Island Jim Connecticut No. 2" |
Wrapper |
Connecticut Shade-Grown (Honduras) |
Binder |
Undisclosed |
Filler |
Undisclosed |
Factory |
Honduras |
Size |
6½" x 52 (No. 2 pencil torpedo) |
Strength |
Medium |
Pairing Drink |
H20 & Homemade Mocha |
Rating |
4.6/5 |