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Whiskey Pairings with Alan Rubin

​Bread and butter, meat and potatoes, wine and cheese, these items have paired on taste buds for centuries. But when Alan Rubin owner of Alec Bradley cigars shows up, there will be no baguettes and herbed butter. The menu is simple – cigars and whiskey, better yet, make that whiskies. Over the years Alan has conducted 50+ pairings for tens of thousands of cigar enthusiasts. Alec Bradley has a close partnership with William Grant & Sons, one of the world’s foremost independent distillers, offering cigars to match with their fine spirits at events around the globe. The liquid lineup includes the likes of Glenfiddich, The Balvenie, and Grant’s latest partner Tuthilltown’s Hudson Whiskey, a handmade American craft whiskey. Great cigars and great whiskey, and no one can pair them up better than Alan Rubin. Trust us, he has done the research. At we sat down with Alan to do some pairings which we’d like to share with you today.

Alec Bradley Prensado & Glenfiddich 15 Year Old
This consistent and finely balanced single malt Scotch contains an intensity of flavor not usually associated with a whisky of this age.  The Glendiddich 15 year old undergoes a distinct maturation process including aging in three types of oak casks before the whisky is finished in the unique Glenfiddich Solera System – a large wood vat that is always kept at least half full.  

Alan feels the Alec Bradley Prensado, Cigar Aficionado’s 2011 Cigar of the Year, is a perfect cigar to pair with the Glenfiddich 15 year old whisky.  The single malt’s complex profile, including notes of dried fruit, honey, warm spice and marzipan, marries beautifully with the Prensado’s spicy, sweet chocolate, and leathery character.   After trying this pairing, you’ll agree that the Alec Bradley Prensado and Glenfiddich 15 year old single malt Scotch is a match made in heaven.

Alec Bradley Coyol & Glenfiddich 21 Year Old

Glenfiddich 21 year old Scotch has an exceptionally complex and evolving profile that progressively discloses more depth. The Malt Master carefully guides the finish process, which takes around 4 months and includes aging in barrels that formerly held Caribbean rum, by regularly sampling the casks to guarantee the Scotch has achieved the ideal finish.

A whisky that has been so painstakingly crafted should be matched with a premium cigar that has been fashioned with similar attention to detail and artistry.  To that end, Alan considers the Alec Bradley Coyol as a perfect companion for the Glenfiddich 21 year old.  The Coyol’s bold spice and sweet notes of cherry and nutmeg mesh marvelously with Glenfiddich 21’s notes of pepper, earth, lime, and vanilla.  The interplay between this cigar and whisky will have you revisiting this indulgent combination time and again.  

Alec Bradley Connecticut & Monkey Shoulder
Monkey Shoulder’s name pays homage to the plight of malt-men working long shifts turning barley by hand.  Over time, one arm would hang down a bit lower than the other, resembling a monkey, hence the nickname “monkey shoulder.”  Monkey Shoulder Blended Malt Scotch Whisky is the world’s first triple malt which signifies the blending of three single malts from three of Speyside’s premier distilleries.  The end result is an exceptionally smooth and rich whisky.

Alan chose the Alec Bradley Connecticut to pair with Monkey Shoulder Scotch due to the mellow characteristics of both cigar and whisky.  The vanilla and whispers of spice in Monkey Shoulder harmonizes beautifully with the Alec Bradley Connecticut’s sweet cedar, earth, and creamy nuances.  Sit down with the Alec Bradley Connecticut and Monkey Shoulder Blended Malt Scotch Whisky and you’ll concur they are a dynamic duo.  

Alec Bradley Black Market & Hudson Four Grain Bourbon
Hudson Four Grain Bourbon is the first pot-distilled whiskey to be made in Hudson Valley, NY since the Prohibition.  This small batch artisanal bourbon uses locally sourced heirloom corn, rye, wheat, and barley, to achieve a complex and expansive character.  The bourbon is patiently aged in petite new American Oak barrels, which provide more contact with the wood, providing greater depth and a warm soothing finish.

While many of his blends would complement Hudson Four Grain Bourbon, Alan selected the Alec Bradley Black Market.  This particular cigar has the requisite complexity and flavor profile that relates ideally to the essence of Hudson Four Grain Bourbon.  Alec Bradley Black Market’s bountiful bevy of spice and pepper and its long dry finish dance perfectly with Hudson Four Grain Bourbon’s balanced, peppery, and rich qualities.  You won’t find a better union than the Alec Bradley Black Market and Hudson Four Grain Bourbon.

Alec Bradley Mundial & Hudson Manhattan Rye
From grain to glass, the award winning Hudson Rye is meticulously crafted and produced using only the finest locally sourced ingredients.  Exemplifying the artisanal spirit, the distillery-men take a hands on approach and wrestle with the rye grain, which is notoriously difficult to work with, to achieve an honest rye whiskey that’s both bold and smooth.

The Alec Bradley Mundial, a special blend that features two binders and four distinct fillers, is Alan’s recommendation to enjoy with Hudson Manhattan Rye.  The Mundial’s bold, meaty, and spicy profile exquisitely partners with Hudson Manhattan Rye’s balanced rustic, spicy vibrancy.  As the decadent flavors from the whiskey and cigar intermingle you’ll wile away the hours in a state of true bliss.

At the end of the day, any glass of whiskey will make a fine accompaniment to your cigar as long as you enjoy it. To get to the level where the subtle flavors of the cigar and whiskey perfectly complement each other will take some time and exploration. Alan suggests matching the intensity of whiskey with the intensity of the cigar so the pairing works together instead of one component overshadowing other. To become an expert in pairing, you’ll then need to pick out flavors that work well together. Spicy and sweet, toasty and creamy, peaty and earthy, the list is never ending. Doing the testing is half the fun, we encourage you to develop your own pairings and share them with a friend.

Share your pairings on our community forum at:​.

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