First's the Worst, Second's the Best

Whats one of your top favorite cigars?


Pencils down.

Or in this case, pencils down and cigars up.

The Island Jim #2 is an amazingly tasty cigar that is the shape of a pencil. Funny right? A #2 pencil specifically. A torpedo shaped cigar, the tip of the cap is a dark maduro color, and then theres a light tan Connecticut wrapper color. Following it is the same dark maduro color that makes up the remainder of the cigar, literally making it look like a fat pencil.

The Island Jim #2 is a collaboration with Oscar Valladares, the owner and found of Oscar Cigars. Oscar loves a local cigar shop in Pittsburgh, Pennsylvania called the Leaf and Bean. Its a cigar shop ran by none-other than Jim… who would’ve thought? Haha.

If you want to picture who this crazy but passionate cigar shop owner is, simply look to your label. It’s an exact replica of Jim, in his island-esque appearance. Often seen in a Hawaiian shirt, with frizzy grey hair. Now neither of the two will spill what exactly the cigar leaves are, but we do know that Oscar makes his cigars in Honduras.

Looking at the cigar, it has a foot that is not completely wrapped by a wrapper leaf. That means the binder leaf frays out a bit to give the pencil a unique appearance. The cigar looks like a pencil used to write a review about a cigar, then erased what they wrote, only to change it and erase it again! Thats not the case today though. I felt like I got everything the Island Jim has to offer and I was not disappointed. Oscar’s cigars tend to always have some unique quality with their appearance using tobacco.

I decided to go with the advised route. That was to cut just the tip of the cap off so that the Connecticut wrapper is exposed. A cold draw gave a sweetness that I couldn’t put my finger on. I then gave it a light.

Boom, it him me.

It was sweet tea! Not that crappy McDonalds sweet tea that tastes like syrup, but a strong southern sweet tea. The good kind.

The initial light of the cigar was difficult, I’ll admit. Due to the leaves fanning out some, it was hard to get/keep an even burn until the burn line got to the wrapper. The cigar doesn’t give you a ton of smoke not the draw, which I normally prefer. It stays on the lighter side, but the cigar itself smokes like a champ. I get hints of wet hay, newer oak barrels that are empty, and a flavor profile that wants to make an appearance but is not ready.

As it burns, the burn line started to canoe (where one side is further down than the other) so I gave it a very minor touch-up (note, this ends up being the only time a touch-up is needed). Slightly weird, but the cigar gave me a dry mouth for the beginning of it. I used to get dry mouth when I first started smoking cigars, but I haven’t experienced that in a very long time. So strange.

As it burned I caught a whiff of smoke that brought me back to the flavor earlier that didn’t want to show itself. It was cherry. A strong cherry wood profile that lingered in the smoke that left the foot of the cigar. One of my favorite smells.

Now this is a medium to full body cigar, but it never kicked me out of the ring. As it progressed to the second third the dry mouth disappeared. There’s a slight chocolate after taste. Not enough to say it has a chocolate profile, but enough that I can detect it. By this point the main odor I detect in the smoke is strong cherry wood. This second third has been extremely consistent.

Before the burn takes the label I decide to transition into the final third. I cut the head of the cigar again to remove the Connecticut wrapper. This leaves me with nothing but the dark maduro cigar. Of course because the top of the torpedo is gone, the draw is even easier. Now I can experience a whole new cigar!

Instantly I get hit with strong chocolate and cherry wood tastes. Theres a slight pepper hint, but to be fair I feel like I can always taste pepper on a final third. Maybe thats the heat trying to singe my moustache. Need to be careful… the finance likes the moustache.

As I wrap up the cigar before it singes the ‘stash, I pull in strong cherry notes. Not the traditional cherry like the fruit but more of a cherry soda. Such a unique flavor to detect in a cigar.

I take my final draw on the cigar, and lay it down to rest. Overall a wonderful experience. I have yet to have a cigar made by Oscar that wasn’t a wonderful experience. Although the cigar is labeled #2, I’d say it’s a #1 in my book.

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