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Foundation The Upsetters The Skipper Cigar - 1 Single

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  • THE UPSETTERS

    Jamaica has a deep-rooted tradition of embracing the underdog - the anti-hero who defies the odds. Upsetters are rule-breakers, the game-changers, the ones who challenge convention. In the 1960s, Jamaica's "rude boys" watched old spaghetti westerns, seeing themselves in gunslingers like Django, figures who stood tall against the establishment. It was this same rebellious spirit that gave birth to reggae music, a sound that shook the world.

    The Upsetters cigar line is a celebration of Jamaican. At its core is the legendary Jamaican Cow Tongue tobacco, a rare and unique leaf cultivated in the very same hills where the indigenous Arawak people first planted tobacco centuries ago. The Upsetters honour Jamaica's rich history, blending tradition with a bold new edge - because pioneers don't follow rules, they rewrite them.

    Dare to be different. Be an Upsetter.

    Length: 4 1/2"
    Ring Gauge: 38
    Strength: Medium

    Packaging: 1 Single
    Vitola: Figurado
    Smoking Time: 30 Minutes

    Wrapper: Connecticut Broadleaf Maduro
    Binder: Nicaragua and Jamaican Cow Tongue
    Filler: Nicaragua and Jamaican Cow Tongue

  • Earthy and sweet, with notes of cocoa, black pepper, dark fruit, and espresso layered over the signature herbal infusion.

  • FOUNDATION CIGARS

    In 2014 Nick Melillo faced a stark choice - He could well have stayed on as Executive Vice President of International Operations and Head Blender of Drew Estate (a role he had held since 2003), or he could seize the chance to finally use his 20 years of hard-earned experience and his access to the highest quality cigar tobacco to make his own cigars – the cigars of his dreams!

    The choice was easy, and in 2015 Foundation Cigar Company was born, all for the love of the leaf.

    Nick’s cigar journey started in high school, on Saturdays he would go for a smoke with his grandfather and brother at their local shop in New Haven, Connecticut. After memorising all details of every cigar in the humidor; Nick persuaded them to give him a weekend job.

    Nick’s passion for working with cigars was immediately apparent, but following four years at Calabash Shoppe, the wide world was calling, and Nick took off to travel the globe. Following a lengthy global trip remarkably reminiscent of Raiders Of The Lost Ark, it was in 2003 that Nick received a call from Jonathan Drew...

    Jonathan needed someone who knew and loved cigars and was willing to move to Nicaragua to oversee the setup and operations of his new cigar company - Drew Estate. Nick jumped on board and immediately started blending cigars and fermenting tobacco; cigars and tobacco that completely changed the cigar industry in the early 21st Century.

    In 2015 Melillo branched out on his own, finally forming the Foundation Cigar Company.

    Famously and without being prompted, paid or promoted, the cigars are now regularly being championed as the best cigars available by Joe Rogan (the world’s most popular podcaster) and winning awards and ratings such as #1 Best Buy (Cigar Afficionado), Cigar Of The Year (Cigar Snob) and #3 in Cigar Afficionado’s top 25 2019.

    But what is at the heart of Foundation Cigar Company is the cigar smoker themselves – that smoke-filled moment of pure presence, that quietly thunderous connection to ancient heritage, modern science, and genuine passion for the leaf. This is something that Melillo and Foundation Cigar Company will provide endlessly to any who will sit and take audience. All for the love of the leaf.

Packaging
Single Cigar
Ring Gauge
40
Length
4.5000000000 inches
Strength
Medium
Region
Nicaraguan
Smoke Time
30 minutes

Reviews

Displaying 1 to 3 (of 3 reviews)
Result Pages:  1 
by Ollie on Sunday 03 May, 2026
Hard to light, uneven burn and just not an enjoyable smoke at all, gave up after 10 mins
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by Joshua on Saturday 25 April, 2026
Not the worst cigar I've ever smoked but awful nonetheless. I bought this cigar based on Lewis' video review where he said it is not an infused cigar but tastes like one. I should have read the description because this is indeed an infused cigar. I was already hesitant at the threat of an artificial sweetened flavour but the alure of a unique tobacco drew me in. I would liken this cigar to smoking a scented candle. It has a sickly sweet, almost perfumed, aroma and taste. It immediately began to unravel from where I cut it and also from the burning end as well. I had to give up in the last third because it was only burning down one side and had practically fallen apart. And honestly the flavour wasn't worth the struggle. I'm surprised this is part of Foundation's range.
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by Lee on Friday 27 February, 2026
Got to say I was disappointed with this one, after a couple of the ska cigarillos I was looking forward to trying this out but it became apparent rather quickly that this smoke was going to be hard work!!! The burn was very uneven and required more touch ups with the lighter than I'd have liked,the draw was ok but occasionally gave abit of pop n fizz,something I wasn't expecting!!! The wrapper cracked quite early on into the smoke which added to my woes,all in all for me it was a disappointment for me. The only positive for me was that unique cow tongue tobacco taste.
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Displaying 1 to 3 (of 3 reviews)
Result Pages:  1 

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