Leaf by Oscar – Connecticut – Cigar Review

It’s good to have some vacation time and not have to go anywhere. Today I will review the “Leaf by Oscar” cigar. Before I get into the review allow me to introduce the man behind the Leaf – “Island Jim” Robinson. He is the man who owns the world-famous Leaf and Bean cigar cafe in McMurray, PA. established in 1999. He has second location in Pittsburgh, PA.  Jim is by far the most campy cigar man I have ever met. This man can only be described as the Jimmy Buffet of cigars. He has a passion for cigars that drives him to produce some of the most tasty and interesting creations in the business.


The “Leaf by Oscar”  is one of those creations. As he explained to me at this years IPCPR, he went down to Danli Honduras to work with Oscar Valladares on this new blend and left it in the hands of Oscar. As Jim was leaving he asked them to wrap the cigars in a leaf  to bring back to the US. When Jim returned he noticed that the leaf preserved the cigars perfectly.  So the “Leaf” was born. Island Jim didn’t stop there. He decided that the band on the cigar should be organic paper, and we say organic we mean the band is made from the stems and veins of the tobacco leaf; kind of like hemp paper is made. He created a small factory to make the bands and hired single mothers to work there so that they could support their families.  One other point about the band as you will see later, Jim explained to me that since it is made of tobacco it is the only band on cigar that you can actually smoke through. The Leaf by Oscar is truly a unique cigar in today’s crowded field of cigars on the market. The burning question of course is; How does it perform and taste. So allow me to answer that question….

Leaf by Oscar Review

When you first see a Leaf by Oscar cigar on the shelf you may not think it is anything special. In fact if you don’t know what it is you may walk past it, you may pick it up and look at it curiously, and if you are inquisitive enough you would ask the tobacconist about it. What you will learn is that the outer wrapper is a cigar leaf used in lieu of the standard plastic encasements. You will also notice that the Leaf by Oscar comes in 4 different blends presented in a cedar box with wooden placards labeling each tray.







Each blend comes in a 6 x 50 Toro and I was given the Connecticut by Island Jim to review. This blend is constructed from a Honduran binder and filler and an Ecuadorian Connecticut Shade wrapper. The sample has been resting in my Humidor for 5 months  now and I am glad I had there for that long. Based on some previous reviews I would say the time helped it to blend some morre and develop a balanced flavor.

The outer leaf wrap was still pliable and opened up nicely to reveal the prize inside. A lovely Ecuadorian Connecticut wrapped cigar. The wrapper is a little veiny and there were some small green blotches here and there, but overall it looked ready to be smoked. It has a perfect triple cap and had a scent like that of fresh tea and sweet tobacco.

Leaf by Oscar - Connecticut

Leaf by Oscar – Connecticut


Clipping the head and giving it a dry draw the Leaf by Oscar demonstrates that it is going to be a wide open, unrestricted smoke, and should give mouthfuls of flavor. The band is simple, an off-color tan and black simply stating LEAF by Oscar. This is truly a tribute to Oscar Valladares and Jim is quite proud of this creation.

Firing it up there was a little touch of spice and no typical Connecticut Shade bitterness. There was an incredible smoke coming through that offered flavors of deep mocha and nuts. I would describe it as an ultra creamy smoke. The burn was perfect  and the ash was a nice light grey to white.

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As it transitioned towards the second third the was a delightful citrus note coming through  that stayed for quite some time. The retro-hale was clean and easy on the nostrils. The smoke is still rich and creamy and the wrapper is developing a nice oily sheen to it.  The burn line has been razor-sharp and the ash is impeccable so far.  I only hope the ash would hold tight for longer but it fell near the middle of the second third. I am glad I have a wardrobe of shirts dedicated to smoking cigars. I am a candidate for a smoking jacket.

It is a pleasant December afternoon here in Florida, the birds are chirping and there is not a cloud in the sky. It is a perfect day to relax with such a fine cigar  while starting a end of year vacation at home. I am tempted to get some rum as Jim would but I will wait till the end of the second half.

Taking it down to the final third, a peppery retro-hale has developed and the strength has stepped up a notch. I really like the rich blue smoke coming off the foot. There is a sweet molasses aroma off the foot now along with a roasted nut flavor. Of course on the best features of this cigar is that you can smoke it through the cigar band since it is also made of tobacco.


Island Jim and Oscar, you have a wonderful smoking experience here. I look forward to more creations coming out of this collaboration.

– Boston Jimmie


2 thoughts on “Leaf by Oscar – Connecticut – Cigar Review

  • I am always flattered to hear the reviews of the “Leaf by Oscar” cigar. Overwhelmed that you would take the time and effort to share your thoughts on our cigar. For us it is an experience that we are proud to be part of. With so many great cigars by so many great people to be recognized is more than I can put into words. Wahoo! Livin’ the Dream!

    • Jim it was a pleasure hanging out with you in vegas, and yes I did enjoy the Leaf by Oscar a lot. I need to sample the other blends sometime. Live the dream brother it is the only way.

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