General Cigar Co. had a very successful launch this past winter. Rick Rodriguez, who is more or less the face of CAO, modified the CAO La Traviata blend slightly and placed the cigars in aggressive holiday-themed packaging. The cigars were Angry Santa and Evil Snowman, both of which sold well for the company. 

We began hearing murmurs regarding a follow-up summer release shortly thereafter with even more aggressive packaging. It was originally set to be known as CAO Son of Uncle Sam, a modified CAO blend made for the July 4th holiday with its name coming from Uncle Sam and Son of Sam, a serial killer.

After some negative feedback regarding the name, the company opted to call it Sinister Sam. It’s a take on the company’s CAO America blend using dual Connecticut shade and Connecticut broadleaf wrappers, a broadleaf binder and fillers that include Colombian tobacco.

CAO Sinister Sam Box 1

CAO Sinister Sam Box 2

CAO Sinister Sam Box 3

CAO Sinister Sam Box 4

It also features brand new artwork on both the box and main band, while the CAO America’s foot band is retained.

CAO Angry Santa Evil Snowman  Sinister Sam

  • CAO La Traviata Angry Santa (6 1/2 x 52) — November 5, 2013 — 1,500 Boxes of 14 Cigars (21,000 Total Cigars)
  • CAO La Traviata Maduro Evil Snowman (6 1/2 x 52) — November 5, 2013 — 1,500 Boxes of 14 Cigars (21,000 Total Cigars)
  • CAO America Sinister Sam (6 1/2 x 52) — June 12, 2014 — 2,000 Boxes of 14 Cigars (28,000 Total Cigars)

CAO Angry Santa Evil Snowman  Sinister Sam Box 

Like the winter releases, it s 6 1/2 x 52 and comes boxes of 14.

CAO America Sinister Sam 1

  • Cigar Reviewed: CAO America Sinister Sam
  • Country of Origin: Nicaragua
  • Factory: STG Estelí
  • Wrapper: Connecticut Broadleaf & Connecticut Shade
  • Binder: Broadleaf
  • Filler: Colombia & Undisclosed
  • Size: 6 1/2 Inches
  • Ring Gauge: 52
  • Vitola: Toro
  • MSRP: $8.50 (Boxes of 14, $102.00)
  • Date Released: June 12, 2014
  • Number of Cigars Released: 2,000 Boxes of 14 Cigars (28,000 Total Cigars)
  • Number of Cigars Smoked for Review: 3

While you must remove the foot band, there’s definitely a choice that you will have to make regarding the Sinister Sam’s gigantic main band. I opt to remove it on every cigar I smoke except the one I photographed. I find the cigar looks quite awkward without it, because as big as the band is—the dark wrapper is even larger and has a somewhat flat texture once the color from the band is removed. The odd part is, the wrapper has plenty of texture and veins, but it just cannot compete with the band. I pick up some ammonia notes from the darker wrapper with sweetness, hay and grass present. The foot is more appetizing: sweet earth and leather. The cold draw is somewhat similar with muted sweetness, earth, leather and a spice on the middle of the tongue that cuts through things a bit.

CAO America Sinister Sam 2

From the first puff I get a big nuttiness with sweetness following right behind. There’s salty notes and a touch of harshness on the finish, but it does not combine for a much of a bang. Toastiness picks up in both the mouth and around me, which adds another definition. Midway through the first third, shortly before the transition between the two wrappers, I am getting a wonderful salty banana pudding flavor, which is utterly surprising given the start. There’s more predictable flavors, mainly grass and spices, but the core semi-sweet earth and leather notes are the core. Smoke production is great, but on two of the samples the first chunk of ash falls off right around the quarter-inch mark, which was an annoyance.

CAO America Sinister Sam 3

The second third was rather inconsistent draw-wise between the three samples. While all started slightly loose, one sample significantly tightened up, one remained constant and the other loosened up a bit. I preferred the two latter examples compared to the former, which required a re-cut. Flavor-wise there’s a lot of roasted notes added to the core as well as more pronounced paprika and sassafras, a sort of root beer-like flavor. Wet earth is present on the finish, which isn’t the greatest of thing. Strength is medium, a bit lighter than the first third although still very much in range.

CAO America Sinister Sam 4

While I had some concerns about the increasing temperature in the second third, the final third sees the cigar lose a bit of momentum and cools down. More forceful draws are required to keep the Sinister Sam from going out. A big earthy note emerges in the process and an espresso note adds itself into the finish. Unfortunately, grass is now added to the wet earth flavor, which overwhelms some of the more positive aspects.

 Final Notes

  • Credit to General Cigar Co. for disclosing the use of Colombian tobacco. Most companies chose to call Colombian tobacco “Peruvian tobacco.” 
  • As for the original name—is it the most offensive thing we’ve seen in the cigar business? No. Is it the first time we’ve named a cigar for someone who murdered a whole bunch of people? Nope. But was it a good idea? Probably not.
  • There was a ton of work put into the packaging, which includes the Uncle Sam character to smoking a CAO America.
CAO America Sinister Sam Band
  • Speaking of CAO America, it’s probably my least favorite blend in the CAO portfolio. The Sinister Sam was a massive step in the right direction as far as I was concerned.
  • I found the strength to be medium throughout, although it definitely starts out a bit stronger.
  • The inconsistent draws were annoying and troubling.
  • I was a bit concerned about some of the glue I found on these cigars. It’s a problem that appears more with these type of art cigars, which makes a bit of sense, but is still not pretty regardless.
  • Personally, I think the cigar looks quite awkward without its massive band.
  • On that note, I think it would have been good to put a secondary (or I suppose third) band underneath the large band similar to how La Sirena has handled its massive bands
  • I smoked the new CAO Extreme and found it to be a pretty good cigar, I would definitely recommend it over the Sinister Sam, even if the artwork isn’t as great.
  • The band does a good job masking how big this cigar is, it took me two hours to finish on average, although a large part of that was thanks to the last two inches.
  • Cigars for this review were purchased by halfwheel.
  • Site sponsor Atlantic Cigar has the CAO Sinister Sam in stock, but you must call to order at 800.887.7877.
80 Overall Score

There were a lot of very redeeming qualities flavor-wise for the Sinister Sam. The salty banana pudding note was unique, sassafras—the slightly less sweet root beer note—is a favorite and I think the spices did a good job to provide contrast. Unfortunately, for much of the cigar it was a boring mixture of earth—in varying degrees of wetness—oftentimes overwhelming the unique characteristics. Furthermore, never once did the flavors seem to work at developing a profile that was greater than the sum of its parts. Construction was not perfect—the draw was an issue, but otherwise smoke production and burn were more than acceptable. I do not have any objections to smoking another Sinister Sam, but I’m not sure it’s good enough to recommend purchasing one.

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Charlie Minato

I am an editor and co-founder of Media, LLC. I previously co-founded and published TheCigarFeed, one of the two predecessors of halfwheel. I have written about the cigar industry for more than a decade, covering everything from product launches to regulation to M&A. In addition, I handle a lot of the behind-the-scenes stuff here at halfwheel. I enjoy playing tennis, watching boxing, falling asleep to the Le Mans 24, wearing sweatshirts year-round and eating gyros. echte liebe.