Island Jim #2 by Oscar Valladares Tobacco and Company | Cigar Review

Wrapper: Undisclosed
Binder: Undisclosed
Filler: Undisclosed
Size: 6.25 x 54 “Figurado-Torpedo”
Body: Medium
Price: $10.00





Today we take a look at the Island Jim #2 by Oscar Valladares Tobacco and Company.
Thank you John.



Island Jim #2 debuted at the 2014 IPCPR trade show.
Factory: Oscar Valladares Tobacco & Company.

Jim Robinson, a Pittsburgh businessman, collaborated with wild man extraordinaire Oscar Valladeres to come up with the Leaf by Oscar line.
Robinson must make a helluva an impression on cigar makers as Ortega used the Island Jim name for one of his 12 cigars in the Wild Bunch series back in 2013. (Each and every stick reviewed here).

Robinson chose not disclose the leaf stats. Why buddy? This isn’t the cure for cancer. It ain’t friggin missile codes. Go figure.
I’ve read several reviews where there is more than enough information about everyone involved. Zzzzzz….If you need to read about the lives of these people, there are plenty of reviews out there to glean that info.

The Island Jim #2 by Oscar Valladares is certainly an odd looking bird. The pencil point cap is a nice work of art with a maduro tip and a Connie strip beneath it. According to Rodrigo Cigars, the #2 designation is a pencil reference.
About half an inch of shaggy foot makes it appear wild and crazy.

This is a solid stick. A gorgeous wrapper that appears to be a Colorado or Rosado hue. A medium brown with hints of red. It looks like my shooting belt with a nice organic leather sense to it.

Seams are invisible. Very few veins. And of course, the wild and crazy Island Jim on the cigar band completes the immaculate presentation.
Now does it taste good?

From the shaft, I smell a sweet fruity aroma, spice, cocoa, and coffee.
From the shaggy foot, I smell strong barnyard and spiciness. Also bits of anise and marzipan.
From the carefully clipped cap (I feel like a moil), I smell cocoa, spice, leather, and cedar.

Lighting up a shaggy foot has never been a strong point for me. But here goes nuttin’ honey.
There is a plug creating a draw problem. I pull out my cigar awl and clear it. The draw is now perfect.

The first flavors are: Sweetness, spice, extremely rich tobacco, massive quantities of chocolate and coffee, something I can’t put my finger on but I will nail it soon, nuts, creamy, cedar, and leather.
The chocolate is serious hot cocoa with marshmallows.
I got the missing link: Floral notes. Huzzah!


Strength is medium body.
This is probably the first time I’ve had zero problems with lighting a shaggy foot. Nicely done Uncle Katman. (Yes, I talk about myself in the third person now.)

I thought I was told by someone that this cigar had a sweet tip. It doesn’t. Another blend maybe? I can’t remember.
This is a real candy bar of a blend.

Side Note: This is very cool. I won something for the first time from a cigar contest. I entered a contest that Ventura Cigar Co. promoted. I always enter using my real name. No Katman bullshit. And I won this back lit poster in a nice Plexiglas frame. It’s over 2 feet high and came in this giant, massive box from UPS.


It immediately reminded me of the movie, “Christmas Story.” Where the dad gets a plastic woman’s leg lamp in a giant box and yells out, “I’ve won a major award!”
Dad: “Aaah! “Fra-GEE-leh!” It must be Italian!”
Mom: “Uh, I think that says FRAGILE, honey.”
Dad: “Huh? Oh, yeah.”


Back to the Island Jim #2 by Oscar Valladares. This cigar is so jam packed that I might finish it by noon. Or 4-1/2 hours.
35 minutes in, I’ve smoked 1-1/2”. And the ash is really boss. Hanging Ten, dude. (Yeah we really talked like that growing up in So. Cal.).
Almost a perfect char line. Perfect draw. And to top it off, a chocolate nutty creamy candy bar to smoke.


Smoke time is 40+ minutes.
And it is here that the ash disembarks the mother ship.

All of my expectations about the Island Jim #2 by Oscar Valladares were wrong. I must be thinking about another brand or blend. This is a dynamite cigar.
The stick is very complex now. But only a medium finish.


The hole I made with my cigar awl seems to have healed itself because the draw is tight again. So once more with feeling.
Fixed. This time the plug was beneath the cigar band which I had not traversed the first time. I stopped just short of it. I’m always afraid of cracking the wrapper. But then, I’m a master poker. (?)

I’ve hit the sweet spot. Major flavors. Major complexity. Nice balance. Long finish.

Chocolate and creaminess really run the show. The black pepper has been here from the start but seems to have settled in at the halfway point of the flavor list.
Strength is medium/full.

And then flavors flatten out. It got me all excited and then let me down.
What the hell happened? There was a blackout.


Most of the flavors are gone. I hope this is momentary. I was on the road of rating this cigar with a very nice number.
All that is left is some sweetness, spice, and a touch of chocolate. That’s it!
Lawdy, lawdy mama.

It’s like a Stephen King story. The man sitting in a dimly lit den smoking his favorite cigar and sipping only the finest brandy. The lights go off. The cigar loses its taste. The brandy snifter crashes to the floor. And a dark ninja dressed figure walks in quietly and from behind the man, slashes his throat. That’s what I’m feeling.
Who says Alzheimer’s ain’t fun? LOL.

I guess I shouldn’t make this a laughing matter but it is the only way I can get through this. Charlotte cries a lot. I see the shocked faces in friends, and daughter, when I can’t remember their names or events. They think I’m being funny. And we all know that I’m not funny. It’s a shame. I’m even having trouble processing my cigar photos now. I get confused about how to do it.

I believe that the Island Jim #2 by Oscar Valladares is beginning to return. Small steps.
“Bob Wiley: You ever hear of Tourette’s syndrome? Involuntarily shouting profanity?
Dr. Leo Marvin: It’s exceptionally rare.
Bob Wiley: Shit-eating son-of-a-bitch! Bastard, douche-bag, twat, numb-nuts, dickhead, BITCH!
Dr. Leo Marvin: Why exactly are you doing this?
Bob Wiley: If I fake it, then I don’t have it.

The sweetness is now dominating the flavor profile. The spice is gone. So is the chocolate…almost.

Smoke time is 65 minutes.
The halfway point photo is sort of weird. Jim’s face is so big it reminds of Slim Pickens riding the nuclear bomb in “Dr. Strangelove.”


The comeback has risen from the grave. Plus a few new flavors.
Here it is in living color: Chocolate, creaminess, coffee, spice, nuts, toasty, floral notes, anise, raw almonds, cedar, leather, and that very rich tobacco.
Wow. That scared the shit out of me.


Anytime you have a figurado, torpedo, or belicoso, using the halfway point isn’t really right. Because the last inch of the cigar is usually unsmokeable because it is too small.

The flavors are back but not at the fiendish blood curdling excess that was the first third.
I don’t get it. It is a roller coaster for “shore.”

It’s a nice cigar but something is wrong. Most of the big guy reviewers always smoke 3 cigars before the review cigar. It allows them to compare and look for consistency. When one has only one cigar, I gots to takes my chances, Bub.
So I have no idea if this is typical of this blend. I hope not.

This smoke is a long one. Too long for a roller coaster of flavors coming and going.
I re-light the cigar and suck the shit out of it. That’s the ticket. It brings the monster back to life, Eye-gor.

Flavors are back. Although, I find it hard to believe that really hard sucking did the trick. But at least I get to finish the cigar with a very nice blend in my mouth.
Construction is superb. Char line is spot one. Only a couple minor corrections.

Smoke time is one hour 25 minutes.

I’m conflicted. There are no major transitions. Same flavors. All day, all of the time.
Transitions is what makes a great cigar. Instead of a lumbering ox.


The sun really shows off how beautiful the wrapper is. (My English teachers would have a shit seeing me use a preposition to end a sentence).
At this point, I can’t conjecture any further than say the Island Jim #2 by Oscar Valladares is anything more than a very pleasant cigar.

I read some reviews and they are split down the middle. To me, that reads as inconsistency. If I were a rich man and had a second stick, I’d open this cigar and take a look inside. Doing an autopsy if necessary. There might be an answer there.
The Island Jim #2 by Oscar Valladares smokes like a short filler cigar. Bursts of excitement met by bouts of boredom.

I’m going to review the La Mission du L’Atelier from Pete Johnson tomorrow. I am really looking forward to that. Pete is a monster blender. No pun intended.

I’ve reviewed a few of the Leaf by Oscar blends and they were OK but not exciting. The presentation overwhelmed the flavor profile. If you have some of these sticks, they will never mature correctly if you leave the corn husk tobacco leaf on the cigar. Get rid of it and leave the cigars to rest in your humidor naked.


The strength falls back to medium+ body. It is losing its oomph.

The draw returns to being very stiff. This shouldn’t happen. Too many plugs. I use the cigar awl and clear the plug and in doing so, crack the wrapper near the foot. My bad.


Taking huge sips of water helps bring back the flavor profile temporarily.
The Island Jim #2 by Oscar Valladares ends very cool. No nicotine. And not a hint of harshness.
But where are those wonderful flavors?
Once again, the cigar is plugged.
The last 1-1/4″ sees the flavors all return in force. But too little too late.
Final smoke time is just shy of two hours.

I just don’t know is this cigar is worth $10. The inventive construction can’t be cheap as it must be rolled by very experienced rollers. And from what I’ve read, that’s all Jim uses.
Plus he is a small boutique brand. Nothing is cheap with these guys. I’m pretty sure his mark up is low.
I would need a couple more sticks before I could make an educated assessment. Sorry.

The Island Jim #2 by Oscar Valladares started off with a big bang. It was full of rich flavors. I thought I was going to be blown away by it. Instead, disappointment reigned the day.
It’s a shame really. Such beautiful construction.
Based on a single sample, I cannot recommend this cigar.
The last third was as dull as a butter knife.

Maybe the blend needs 6-12 months of humidor time.
The problem is that most reviewers don’t tell you how long they’ve had the stick. Especially, the very young guys. There are exceptions of course.
OK. I’ve dug a hole for myself by promising to rate cigars. Here it is: 86.
If you had a completely different experience than me, leave me a comment. I don’t feel I’ve been fair with only one sample.

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7 replies

  1. Sorry you are going through this Phil. Nice review, and I have been wanting to try these.

    BTW I would like to read your reviews on all of the WILD BUNCH, but I don’t see a link for them, can I just search for them or what???

  2. I had a very similar experience…although (like you have) really enjoyed the Leaf by Oscar.

  3. Simply go to the “Search Window” and type in Wild Bunch.
    Thanks Mickey for your thoughts and kind wishes.

  4. I always enjoy your reviews for your honesty…(shooting from the hip if you will). Where do you find these cigars? Many of them I’ve never heard of. Thanks for shooting straight

  5. I have the good fortune of living in Pittsburgh and met Jim just this past weekend at his location in the Strip District. I also want getting a ton of variety out of this cigar – so I pulled out my bottle of whiskey and mixed it with a little seltzer. Something about that combination set this cigar off on a different plane. The two sets of flavors (a blended scotch and this cigar) just played exceptionally well together, The price point is a little steep, but I don’t mind paying it for the positive atmosphere (live music, good people, and a location as eccentric as its owner).

  6. Dear kattmann you need to cut the Connecticut end off the cigar off at about the halfway point of the smoke you will get a different flavor profile I don’t have a clue how this works but it does just as the website says it will I love your reviews God speed to you

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