This pairing matches Foursquare‘s complex 12 Year Private Cask Selection Rum with the bold & robust, Sinistro Mr. Red toro cigar.

They were chosen for the likelihood of the prominent sherry taste in the rum lending itself well to the commonly perceived bold chocolate notes within the cigar.

The Sip:

Foursquare Owner and Master Distiller Richard Seale is a 4th generation Barbados rum distiller who has been awarded IWSC Rum Producer of the Year for 2015, 2016 and 2018. Among serious rum enthusiasts, Foursquare releases are highly sought after, and at times difficult to come across.

This 12 year 2020 release, which has received finishing in ex-bourbon and ex-sherry casks, is said to have notes of dried fruit vanilla and toasted oak. Its color exhibits a dark brown with a cherry red tint and has no added sugar or coloring.

Its finish is purported to be long and honeyed sweetness with a touch more oak.

The Smoke:

Featuring an attractive, smooth and relatively oily Mexican San Andres wrapper, Ecuadorian binder and combination of Dominican, Nicaraguan and Pennsylvanian (USA) fillers, the Sinistro Mr. Red is touted as being a bold and rich cigar that is known to release plenty of cocoa, coffee, nuts and white pepper spice.

It is expertly assembled and brought to life by La Aurora in The Dominican Republic.

Today, I smoke the toro sized release.

The Pairing:

Initially, I nose The Foursquare before I implement a straight cut on the shoulder of the cigar with a pair of cigar scissors. The nose quickly gives off some oak, vanilla, sherry and candied fruit such as apricot. I have not added water. As this is my first experience with the rum – I decide to sip this one truly neat.

A Corkcicle glass with rum and a dark-wrapper cigar

Taking a first sip prior to lighting the Sinistro hits me with a strawberry’ Twizzlers’ licorice sweetness, a tannic wine quality and caramel.

Prominent strawberry on the finish with oak.

Mr. Red (which has an easy-to-light shaggy foot) releases plenty of smoke off the hop, with a salted chocolate essence on my lips from the wrapper. The first few puffs produce ample cocoa and salty cashew (tactile salt taste from the wrapper fusing with a nut taste from the smoke). Additional black pepper for sure.

Some mesquite and cinnamon appear after I sip the Fourquare.

[NOTE: Upon pairing a cigar with brown spirits (especially bourbon), I very frequently perceive cinnamon. Rum, cognac or whiskey. The heat from the cigar, coupled with the sweetness of the rum forge an unmistakable cinnamon hearts taste in this cigar – the kind your secret crush may have given you on Valentine’s day as a kid in school alongside a cute animated scratch n sniff card…]

Deep into the 2/3, Mr. Red bears plenty of chocolate and cedar, and evolves into a rich, dark roasted coffee flavor. Mesquite pops up along with the ever present cashew – which hangs around pretty much throughout the entire cigar from start to finish. I enjoy the nutiness of this cigar.

Some bit of anise becomes present in the Mr. Red, which begins to create a slight grassy, vegetal finish to the rum, which is medium in length and somewhat drying. Having some water eases this as always. The Mr. Red turns into a burnt coffee and dark chocolate bomb as it burns deep towards the final third.

And So…

A lovely combination is formed between this Foursquare 12 Year Private Cask Selection Rum and Sinistro Mr. Red.

Foursquare’s finishing in sherry casks is very evident, and lends sweet cherry and strawberry notes to the experience with a red fruit-sweet, oaky finish (the only single downside is because of its dry character).

Total smoking time was 1 hour and 23 minutes and required 1 touch up. A beautiful, tight, salt and pepper ash held on strong into the bottom of the 2/3 of the cigar.

As expected, the Mr. Red’s powerful chocolate notes meld wonderfully with the rum’s natural sweetness, and a slight vegetal grassy element made things very interesting (but never unenjoyable), therefore, I’ll do these two again, no doubt.

Kurt Bradley

Kurt Bradley is the founder of The Gentleman’s Flavor, to which he is also a contributing editor, host and curator.

Kurt is a certified Whisky Ambassador accredited by The Scotch Whisky Association and has achieved Level 2 Award in Wine & Spirits Education Trust with distinction.

For the purpose of reviewing, he enjoys a cigar alone – but much prefers the company of others.