Bourbon barrel-aged cigars might be nothing new, but that doesn’t mean that the average cigar smoker knows how this influences a cigar flavor profile. Unbeknownst to much of the public, legacy cigar manufacturers like Perdomo have been aging a vast array of cigar tobacco selections in bourbon barrels for decades and just not blatantly advertising the act. 

The only reason the cigar-smoking masses finally got hip to this fact was due to the promotion of this methodology as a form of marketing, which in many cases did not occur until well into the modern century.

But there are plenty of boutique cigar brands out there who have also been taking old booze-laden barrels and giving them fresh purpose as tobacco aging vessels. 

Perhaps one of the most widely recognized of these fresh boozy tobacco leaf faces is AJ Fernandez’s “Diesel Whiskey Row Rabbit Hole Bourbon Barrel Aged” line of cigars. A tobacco offering that pushes the envelope and then makes you want to lick it and seal it with a kiss, all but in a refined, tasteful manner.

Speaking of taste, how does this oversized “Whiskey Row” Toro-shaped cigar type from Diesel smoke once set ablaze with a cedar spill or torch lighter? And should it be accompanied by a glass of bourbon? 

Or should one take this boutique premium cigar blend, and attempt to pair that cigar type with other forms of alcohol for an entirely different cigar flavor profile? Let’s find out, shall we?

Unlit Impressions

Double-banded top and bottom, with both bands being of significant size, this 60 ring gauged, 6-inch long “Gigante” sized Toro from Diesel Cigars is a hefty serving of damn near everything. 

Gorgeously rolled, with nary a sign of blemish or rough vein to be seen, the five-year-aged Ecuadorian Habano cigar wrapper on the outside comes cleanly capped, and due to its slick packaging, is strikingly stylish.

A whiff or two from the unlit foot is all sticky sweet bourbon barrel goodness, unrefined sugar, and a spicy pop of farmhouse funk and Nicaraguan tobacco. There’s also splashes of vanilla and a hint of allspice on the nose when whiffing on that shiny red Habano cigar wrapper.

Dry tasting cold pulls are nuanced by a surprisingly subtle level of sweetness, and a peppery nicotine punch along the palate that is impossible to misidentify. As a cigar type, Diesel’s “Gigante” version of this collab project is a giant drunken stick of tobacco dynamite that’s set to explode in a blast of boozy brilliance at any moment.

Tobacco Nerd Note: According to sources close to the project, repurposed Rabbit Hole Distillery bourbon barrels first began arriving at AJ Fernandez’s facilities in 2016, leaving him ample room to tinker with this previously unfamiliar form of alcohol-infused tobacco aging. 

Initial Smoke

Fuse lit, this creative collaboration venture between the two very different boutique adult-oriented brands slowly began to burn. 

Due to its intensely sweet whiskey aroma, one might expect to find loads of bourbon flavor right away. But for this large cigar, Rabbit Hole’s bourbon ingenuity doesn’t truly begin to hop onto the scene until well into the 5 minute mark. Subtle yet welcoming, the sticky mash sweetness caramelizes and blends with retro nasal exhales that showcase a fair deal of nicotine strength.

There’s also a prominent scent of cedar shavings that starts to form once the first half begins to transition. The result is aromatic plumes of dense smoke that will likely prove to be quite pleasing to those around you, regardless of whether or not they are cigar smokers.

Tobacco Nerd Note: After many months of testing, AJ discovered that utilizing a blend of five to eight-year vintage long-filler tobaccos was the card that had been missing from the deck all along. Plucked from his farms in the Ometepe, Jalapa, and Condega regions of Nicaragua, AJ’s proprietary blend of bold internal tobacco strains provide the backbone that the bourbon barrel-aged Mexican San Andres binder leaf required from the get-go. 

The Second Half

As the prodigy of skilled distillery artisanal minds and the ever inquisitive inclinations of one of the world’s finest next-generation master blenders begins to transform from medium to full at the halfway point, a few things happen.

First of all, there’s the flavor of the cigar, which to this point has been sweet and sticky But it  starts to get a bit drier toward the halfway mark, and forms a far more cedar-focused flavor and aroma. This is likely due to the slow yet steady burn rate of that 60-gauge ash that’s been, as well as the toasted notes that the Ecuadorian Habano wrapper imparts upon the palate.  

Thus far construction has been nothing short of sturdy (thanks again to that 60-ring gauge), with Diesel’s signature “Gigante” cigar type holding a very nice dark gray ash all the way up to the 50-yard line.

Ash discarded, a potent char flavor begins to build, one that is primed with oaky tannins stemming  from the San Andres bourbon barrel-aged cigar binder. It is here that things take a turn toward the nicotine-rich side of the street too, so be sure to take it easy on whatever booze you’ve been pairing with this bad boy. 

Much like the reenvisioned version of the H. Upmann by AJ Fernandez we recently reviewed, sitting down and buckling up for the final portion of the ride is a calling card for this Nicaraguan cigar manufacturer.

Parting Puffs

As the final half of “Whiskey Row” comes into sight, a “Gigante” slug of intensity forms, with the body, strength, and flavor of the cigar all receiving injections of adrenaline. Forget all of those prior notions of medium-strength smoking pleasure and subtle nuances. AJ Fernandez is flexing all of his cigar blending muscles in the best possible way, and there’s nothing you can do about it but sit back and soak it all in.

By now, those cedar smells from the first few inches of the cigar have returned to tango with your tonsils, and with it so too emerges that dryness from earlier. And as a hazelnut flavor forms, an intensely aromatic, pleasantly long finish reminds you that this cigar has been built for those who prefer to go all-in. 

It may not be taking the cigar world by storm, but Diesel’s “Whiskey Row Rabbit Hole Bourbon Barrel Aged Gigante” is a rollercoaster of smoking sensations. This monolith of a premium cigar blend is about as fun as it gets if full-bodied cigars are your jam.

Brilliantly executed from start to finish, this collaborative endeavor between master distillers and master cigar tobacco blenders serves as a shining example of what boutique cigar making is, and should always be, all about. Making amazing adult-oriented consumable products that are guaranteed to be remembered and revisited for years to come. 

Stogie Specs

Shape: “Gigante” Toro

Wrapper: Ecuadorian Habano

Wrapper Shade: Colorado Claro/Rosado

Binder: Mexican San Andres

Filler: Nicaraguan (Condega, Jalapa, and Ometepe Blend)

Origin: Nicaragua

Strength: Medium-Full

Length: 6-inches

Ring Gauge: 60

Smoke Time: 90-120 minutes