When Toasted Oak Meets Dark Tobacco

As I prepared to head out to the screen porch for an evening smoke and sip, I was in the mood for an Old Fashioned. I quickly mixed the drink right in the glass and dropped in a large ice cube. In the interest of brevity, I skipped grabbing an orange peel. A dash of orange bitters made up for its absence. I did not, however, forgo the requisite Luxardo cherry.

For the spirit, I opted for Elijah Craig Toasted Barrel, hoping its toasted oak and caramelized character would give the cocktail a slightly smoky edge. Despite the mixologist shortcuts, the drink proved enjoyable and flavorful.

I selected an Aganorsa Leaf Rare Leaf Reserve Maduro to accompany the Old Fashioned. The cigar uses a Mexican San Andrés Maduro wrapper over Nicaraguan binder and filler. It’s a full-bodied cigar that delivers rich and complex flavors of dark chocolate, coffee, and cedar, with mild pepper and a touch of sweetness emerging on the finish.

The Toasted Barrel Old Fashioned brought a mild smoky, caramelized character that echoed the dark, sweet profile of the cigar. Early in the pairing, the cocktail’s vanilla and caramel notes balanced the cigar’s sweeter chocolate and creamy notes. As the smoke progressed, the Aganorsa’s darker espresso, cocoa, and spice notes increasingly came to the forefront.

The tobaccos combined to produce a substantial, earthy Nicaraguan core beneath the cocoa and coffee. Even as the cigar became richer, the toasted oak and vanilla of the Old Fashioned complemented that richness while adding a subtle lift to the pairing.

Overall, this was a natural match. The maduro’s dark, sweet tobacco character paired especially well with the toasted oak and caramel notes of the cocktail, with the whiskey’s vanilla helping to soften and balance the cigar’s deeper flavors. The compact cigar also made for a relatively short smoke, lasting just about 50 minutes — long enough to enjoy the pairing without turning it into an all-evening affair.

Sometimes taking a few shortcuts is worth it.

Cheers!

A Cigar with a Mission: Surpassion King of Battle

Last week I finally found time to drive out to Slow Burn Cigar Co. in Remington. Travel and a busy schedule had conspired to keep me away for more than a month. I was excited to get back and see what was new on the shelves.

The Comfortable Lounge at Slow Burn Cigar Co.

I was also thrilled to finally try a cigar I’d been wanting to smoke for some time: the Surpassion King of Battle.

Surpassion is a veteran-owned cigar company founded in 2024. A portion of every sale goes directly to charities supporting our nation’s veterans and their families. I’ve been seeing praise for the company’s cigars online with increasing frequency, and Slow Burn only recently began carrying them. Surpassion currently offers three core lines, with more on the way.

I selected the Surpassion King of Battle Toro, a cigar whose name pays tribute to the 250th anniversary of the U.S. Army. It features a smooth, oily American Connecticut Broadleaf wrapper over a Mexican San Andrés binder and a blend of Dominican and American fillers. All of the tobaccos have been aged for at least five years.

The King of Battle is a full-bodied, richly flavorful smoke. Dark cocoa and black pepper start things off right out of the gate. Before long, the cigar settles into its rhythm as notes of espresso emerge, accompanied by rich fudge sweetness complemented by a pleasantly bittersweet finish. Smoke production is abundant, while the burn progresses slowly and evenly.

Bold but never heavy-handed, the King of Battle rewards a leisurely pace. Waves of espresso, dark cocoa, and touches of black pepper ebb and flow throughout the smoke, keeping the profile engaging from first light to the final inch. I happily smoked it for more than two hours, down to a warm nub.

I paired the cigar with a bottled green tea, which proved surprisingly refreshing. Even so, I couldn’t help imagining how well the King of Battle would complement one of my favorite bourbons. Since I happened to buy the last one in the box at Slow Burn, I’ll definitely be picking up a few more on my next visit.

Cheers!

Maple, Cedar, and a Summer Evening

We’ve experienced a very wet summer this year, with more days of rain than sunshine. Or at least that’s how it has felt of late, even if we’re told the region is still rated “extremely dry.” For my part, I know there are new washouts in the yard that weren’t there before, and the grass still needs mowing every week.

When the sun does shine for an entire day, it’s an occasion to get outside. On a recent weekday evening, I took advantage of the sunshine to listen to some music, sip a fine whiskey, and enjoy a delicious smoke. Despite temperatures in the upper 80s, with a “feels like” reading pushing 95°, the porch was surprisingly comfortable thanks to a gentle natural breeze and a couple of fans.

I selected the Arturo Fuente Don Carlos Robusto for the evening. The 5 x 50 stick is a relatively short smoke, offering about 45 to 50 minutes of enjoyment. A dark African Cameroon wrapper encases a binder and filler of Dominican tobaccos, with vintage filler leaves aged for as long as ten years. The cigar delivers a medium-bodied profile featuring cedar, sweet coffee, and roasted nuts, with just a touch of pepper on the finish. A natural creamy sweetness remains at the forefront, while the darker, spicier notes provide balance and depth. After six months of rest in the humidor, the cigar performed flawlessly.

Redwood Empire Lost Monarch is an American whiskey created from a blend of 60% straight rye whiskey (aged three to five years) and 40% straight bourbon whiskey (aged four to twelve years). This “bourye” combines bourbon’s sweetness with rye’s spice — the best of both worlds, if you will. On the nose, Lost Monarch offers familiar aromas of vanilla, cinnamon, and a hint of citrus zest. It’s on the palate, however, that the whiskey truly distinguishes itself. Vanilla and maple syrup arrive first, followed by honey and orange peel. The finish brings oak and pepper while allowing the maple sweetness to linger. At 90 proof, it’s smooth and exceptionally easy to sip — perhaps a little too easy.

I chose Lost Monarch to pair with the Don Carlos because its easy-drinking profile seemed well suited to both the cigar’s smoking time and the warm evening. As it turned out, the combination was exceptionally well suited to the occasion. Rather than competing for attention, the cigar and whiskey each emphasized the other’s sweeter side, making for a relaxed, uncomplicated pairing that was perfectly suited to a hot summer evening. The cedar, cream, and gentle coffee notes of the Don Carlos allowed the whiskey’s maple sweetness to shine. The maple syrup note was greatly enhanced compared to when I have sipped the whiskey alone. As the cigar progressed toward richer coffee and espresso notes, the maple character continued to deepen as well, though it never became overly sweet or cloying.

The coffee, maple, and cinnamon notes of the pairing soon had me thinking about breakfast — specifically, a plate of French toast dripping with butter and maple syrup. The flavors in a cigar or whiskey don’t have to be exact matches for the foods they bring to mind. Sometimes the images and memories they evoke are just as enjoyable. It’s all part of the fun.

Cheers!

The Benefits of Procrastination

Lately, as I’ve looked back over many of my cigar and beverage pairings, I’ve noticed an unintended trend. Many — if not most — of the cigars I’ve been enjoying recently had been resting in my humidor for at least a year, and often closer to two. That got me wondering why.

While I regularly pick up new releases that catch my interest, I don’t always get around to smoking them right away. Even after my usual month-long rest following travel, many cigars — new releases and old favorites alike — end up waiting patiently for their turn in the rotation.

As it turns out, that delay isn’t necessarily a bad thing. Several cigars I’ve smoked recently had been aging quietly for more than two years, and nearly every one has been outstanding. (I’m not talking about the truly old “special occasion” cigars that have been tucked away for sentimental reasons. Those are a different story altogether.) Time has generally been kind to these forgotten treasures.

The same phenomenon has crept into my whiskey cabinet. I’ve slowed my bourbon purchases recently, mostly because the shelves are already full. It’s time to work through a few of the older bottles before bringing home more. Whenever I post a picture showing a partially empty bottle, someone inevitably comments, “Looks like you need to replace that one.”

Unlike cigars, opened whiskey doesn’t really improve with age. But stretching a bottle over months — or even years — does have one advantage. Every revisit offers another opportunity to discover a new cigar pairing that I might have missed the first time around.

I recently came across a meme that perfectly summed up my approach to whiskey buying:

I had to laugh because it’s true.

If I’m honest, I’m generally much better at resisting a bourbon purchase than I am at walking away from a cigar shop empty-handed. In fact, I was much better at resisting cigars before I bought the large humidor. Apparently, empty space has a way of convincing you it needs to be filled.

Maybe the solution isn’t to buy fewer cigars.

Maybe I just need more shelves for whiskey.

After all, serious problems call for creative solutions.

Cheers!

Still Has the Muscle: When Boldness Finds Balance

There are evenings when only a full-bodied cigar will do. With plenty of time to relax on the porch, I reached for the lone CAO Flathead V660 remaining in my humidor. After two years of rest, I was curious whether the big Broadleaf-wrapped cigar had mellowed or if it still possessed the muscle that made it memorable.

With its Connecticut Broadleaf wrapper, Ecuadorian Connecticut binder, and Nicaraguan fillers, the cigar delivers rich notes of semi-sweet chocolate and espresso. Sweet molasses and vanilla undertones balance out the dense, darker flavors, and a bit of pepper adds further interest.

The box-pressed 6 x 60 stick is heavy in the hand, and the red and silver American muscle car-themed banding over the dark chocolate-hued wrapper adds to the imposing presence. Although 60-ring-gauge cigars look impressive, they are not comfortable to hold and smoke in my opinion. However, the box-pressed shape narrows one dimension enough to make it feel noticeably less cumbersome in the hand and between the teeth.

Knowing the Flathead’s reputation for bold flavors, I wanted a bourbon with enough proof and richness to avoid being overshadowed. Elijah Craig Barrel Proof seemed the obvious choice.

This bottle is Batch A124, the first of the three releases for 2024. Bottled at 119 proof and aged 10 years, 9 months, it is one of the lower-proof and younger releases in the series, making it especially approachable. The proof is high enough to add interest but never becomes overwhelming. I’ve greatly enjoyed this bottle and will surely miss it once it’s empty.

This bourbon treats the palate with a robust profile of brown sugar, dark caramel, vanilla, and charred oak, along with a moderate cinnamon-laced finish. Vanilla and a hint of tobacco linger in the finish, which is sweet without becoming syrupy, and there’s just enough rye spice to provide a lively finish.

The Flathead’s black pepper and espresso notes dominated the pairing initially. As I slowly sipped the Elijah Craig Barrel Proof, its caramel and brown sugar notes began to balance and soften the cigar’s pepper. Soon, I found myself thinking of richly caramelized crème brûlée.

As the smoke moved into its second half, the cigar's darker espresso and cocoa notes came into the forefront. The crème brûlée impression gave way to chocolate-covered espresso beans as the culinary imagery continued to fill my thoughts.

The CAO Flathead V660 and Elijah Craig Barrel Proof proved to be a balanced and thoroughly satisfying pairing. Even after two years in the humidor, the Flathead had lost none of the muscle that first made it memorable, standing up easily to the bourbon’s richness and proof. In turn, the bourbon’s sweetness tempered the cigar’s pepper, allowing notes of dark chocolate, espresso, cinnamon, and crème brûlée to shine.

Cheers!

A Porch Pairing for a Summer Afternoon

Here’s a summertime pairing that I tried on a whim, and it turned out even better than expected. Samuel Adams Summer Ale is a seasonal release from the Boston brewery that has been a staple of summer cookouts since 1995. The refreshing 5.3% ABV ale features Hallertau Mittelfrüh noble hops, lemon, lime, and orange peels, along with Grains of Paradise. The result is a crisp beer with a light herbal hop character, bright citrus notes, subtle wheat sweetness, and a gentle peppery spice in the finish.

Summer Ale seemed the perfect choice for a warm, rainy afternoon on the screened porch. Wanting a cigar that wouldn’t overpower the beer, yet still offered a satisfying depth of flavor, I reached for a Rocky Patel A.L.R. (Aged, Limited, and Rare) Second Edition in the Robusto vitola.

The A.L.R. Second Edition is a cigar I’ve enjoyed frequently over the years, resulting in numerous mentions here in these Musings. Wrapped in Mexican San Andrés leaf over a Honduran binder and fillers from Honduras and Nicaragua, the medium-bodied smoke delivers satisfying richness while remaining remarkably balanced. Rocky Patel ages the cigars for two years after rolling, and this particular example had spent an additional 22 months resting in my humidor.

The cigar kicks off with notes of espresso and cocoa. As expected from the San Andrés wrapper, a sweet earthiness balances those darker flavors. Rather than dominating the palate, the wrapper’s natural sweetness softens the bitterness of the espresso and cocoa, creating a rich yet approachable combination.

Medium-bodied rather than powerhouse in strength, the A.L.R. Second Edition emphasizes balance over intensity, making it an ideal companion for Samuel Adams Summer Ale. The beer’s bright citrus, wheat, and subtle spice refresh the palate between draws, lifting the cigar’s espresso, chocolate, and earthy sweetness while providing a crisp contrast to its darker flavors.

Pairing cigars and beer isn’t always about matching intensity. Sometimes the better approach is finding complementary flavors that allow each to shine. In this case, the citrus brightness of the Summer Ale and the earthy sweetness of the San Andrés-wrapped A.L.R. Second Edition came together in a way that was both balanced and thoroughly enjoyable.

Cheers!

An After-Dinner Pairing: Angel’s Envy & Perdomo Reserve Maduro

The run of pleasant weather offered another opportunity for an after-dinner smoke and sip on the screened porch. I reached into the humidor for an aged Perdomo Reserve 10th Anniversary Maduro Epicure, one remaining from a purchase about two and a half years ago. After that extended rest, I expected the cigar’s flavors to have melded beautifully.

The Epicure vitola is a 6 × 54 box-pressed cigar featuring a six-year-old Cuban-seed Nicaraguan Maduro wrapper that spent an additional 14 months aging in bourbon barrels. The binder and filler are also said to be 6-year-aged Cuban-seed Nicaraguan tobaccos. Remembering the espresso and nutty sweetness I’d enjoyed from this cigar in the past, I searched for a bourbon with a similarly dessert-like profile.

I selected an old favorite, Angel's Envy Bourbon Port Wine Barrel Finish. One of the first examples of secondary barrel finishing in American whiskey, Angel's Envy helped popularize the concept. The bourbon undergoes a standard four to six years of aging in new charred oak before spending an additional six months in Portuguese ruby port wine barrels. Although bottled at a modest 86.6 proof, the added layer of dark-fruit richness never obscures the bourbon’s familiar caramel, vanilla, and oak character.

The bourbon barrel aging of the wrapper leaf for the Perdomo Reserve 10th Anniversary Maduro adds a layer of sweetness, softening the darker notes typical of the Maduro wrapper. That added sweetness, combined with the dark fruit and vanilla of the whiskey, created an indulgent pairing for this evening's repast.

The Perdomo cigar kicks off with espresso and cocoa notes. Alongside Angel’s Envy’s vanilla and caramel sweetness, the pairing felt decadent from the first draw. As the cigar developed, the molasses and dark chocolate notes became more pronounced. The bourbon’s candied fruit gently softens the cigar’s peppery edge. As the pairing continues and the fruit, chocolate, and coffee notes intertwine, my thoughts drifted to crème brûlée and tiramisu.

The cigar picks up more of a roasted character toward the finish. Rich tobacco and dark chocolate move to the forefront. The rich fruit sweetness from the Angel’s Envy lingers alongside those flavors, bringing to mind dark chocolate-covered coffee beans and cherries.

Secondary barrel finishing has become increasingly popular in recent years, helped in no small part by the growing number of “cigar blend” whiskies. Whether bourbon- or Scotch-based, I can rarely resist these releases when I spot them on store shelves. As I savored this after-dinner pairing this evening, it struck me that Angel’s Envy is particularly well suited to cigar pairing, even though it wasn’t conceived or marketed with that purpose in mind.

“Dessert-like” may be an overused description in bourbon, cigar, beer, and cocktail reviews — even here in these Musings. In the case of Angel’s Envy Bourbon Port Wine Barrel Finish paired with the Perdomo Reserve 10th Anniversary Maduro, however, the description seems entirely appropriate.

Cheers!

The Overnighter: A Bold Cocktail and Cigar Pairing

The Overnighter cocktail is a four-ingredient drink that’s right up my alley as a fan of bitter and sweet combinations. It’s a flavorful, well-balanced cocktail that’s every bit as enjoyable as it is easy to make.

The Overnighter

• 1.5 oz Rye Whiskey
• .75 oz 22.5 ml Campari
• 1 oz Dry Vermouth
• .25 oz Bénédictine
• Orange wheel for garnish

Combine the liquid ingredients in a mixing glass with ice and stir until well chilled. Strain over a large ice cube into a rocks glass and garnish with the orange wheel. Some recipes call for a smoked orange wheel, which would undoubtedly add another layer of complexity.

I used 90-proof Sazerac Rye for my drink. The Overnighter is moderately strong and meant to be sipped slowly, allowing its contrasting bitter and sweet notes to unfold with each taste.

I’ve seen some versions of the recipe call for ¾ ounce of Bénédictine. I tried one using ½ ounce and found the resulting drink a bit too sweet for my taste. The quarter-ounce measure keeps the herbal liqueur in balance, adding depth without overwhelming the other ingredients.

A bold cocktail like the Overnighter calls for an equally bold, well-balanced cigar. I reached for the El Pulpo by Artesano del Tobacco, a cigar I’ve enjoyed often and was one of my favorite cigars of 2025.

The cigar’s rich notes of dark chocolate, black coffee, and roasted nuts paired beautifully with the Overnighter. It had been a while since I’d smoked an El Pulpo, despite still having an unopened box resting in the humidor. This smoke served as a welcome reminder to crack open that box in the near future.

Cheers!