Deadwood Tobacco Co. Chasing the Dragon Midnight Oil 54 x 6 1/4

While they may have never smoked one, seemingly any seasoned cigar smoker has at least heard of a flavored or infused cigar. But a steeped cigar? Not likely.

I hadn’t either until I attended the 2023 Total Product Expo (TPE) this past February in Las Vegas, which is where I was introduced to a collection of steeped cigars from Deadwood Tobacco Co. that are produced in collaboration with Asylum and CLE. It’s called Chasing the Dragon and is offered in three lines: Auntie, Zero, and Midnight Oil.

Editor’s Note: On June 14, 2023, Vaughn Boyd, the former owner of Deadwood Tobacco Co., and Drew Estate filed a lawsuit against Deadwood Tobacco Co. claiming, amongst other things, infringement of a licensing agreement that gives Drew Estate the exclusive rights regarding the “Deadwood” name for cigars.

This cigar, Chasing the Dragon, is one of the cigars the plaintiffs allege is infringing on the agreement.

On June 15, 2023, Christian Eiroa of CLE/Asylum left a comment on this review indicating that the brand would now be known as Asylum 867. 

Given that this cigar was marketed and sold as “Deadwood Tobacco Co. Chasing the Dragon Midnight Oil,” we are leaving the name of this review as it was originally published. 

You can read more about the lawsuit here.

All three versions are Honduran puros with sweetened caps that undergo similar steeping processes to enhance the flavor profile, but the three lines reflect differences in the size and intensity of the steeping process. On the whole, Tom Lazuka of Asylum said the line is about a 4 out of 10 on the flavor intensity scale, with the smaller ring gauges a bit lighter than the thicker ring gauges. The Auntie line is made up of the thinner ring gauges and includes a lancero and corona, Zero includes a robusto, toro and Churchill, while Midnight Oil is made up of the largest vitolas, including a 6 x 60, 7 x 70 and this 6 1/4 x 54 toro extra.

Additionally, all three lines were slated to get a 4 x 32 vitola that comes in 10-count tins, though they were not on the most recent price list and have been put on hold, according to a company representative.

• Deadwood Tobacco Co. Chasing the Dragon Midnight Oil 54 x 6 1/4 (6 1/4 x 54) — $12 (Box of 20, $240)
• Deadwood Tobacco Co. Chasing the Dragon Midnight Oil 60 x 6 (6 x 60) — $12.50 (Box of 20, $250)
• Deadwood Tobacco Co. Chasing the Dragon Midnight Oil 70 x 7 (7 x 70) — $14 (Box of 20, $250)

The cigars officially debuted in March 2022 but were an exclusive release to Deadwood Tobacco Co. in Deadwood, S.D. After that first year of availability, the company decided to make them available nationally, with Asylum, technically CLE Cigar Co., serving as the distributor. While you won’t see Asylum’s name on the cigar or the packaging, its skull logo does appear in the background of the bands.

• Cigar Reviewed: Deadwood Tobacco Co. Chasing the Dragon Midnight Oil 54 x 6 1/4
• Country of Origin: Honduras
• Factory: The CLE Factory
• Wrapper: Honduras
• Binder: Honduras
• Filler: Honduras
• Length: 6 1/4 Inches
• Ring Gauge: 54
• Vitola: Toro Extra
• MSRP: $12 (Box of 20, $240)
• Release Date: April 2023
• Number of Cigars Released: Regular Production
• Number of Cigars Smoked For Review: 3

There’s no indication from looking at the cigars in the bag in which they were sent that these are steeped cigars, as there’s nothing on the band or the paper that wraps the lower portion of the cigar that would indicate such a treatment. The cigars don’t come in cellophane, so I’m intrigued by what kind of aroma I’ll be greeted by once I open up the bag. It’s fairly mild in the sense that it doesn’t jump out of the bag, but if I stick my nose in, I get an aroma of grape bubble gum, and that aroma seems to stick around after I pull a cigar out and set it on my desk. The cigar itself looks good at first glance, though the lower half of the cigar is covered with a thin piece of printed paper, feeling a bit thicker than tissue paper but not as thick as a regular band. Once removed, I see that the wrappers are all evenly hued, with an average amount and size of veins. I’m a bit concerned by the firmness of the cigars, as the first one is firm at first touch but gives way with just a bit of a squeeze, sort of like a thick dough would do. They don’t feel underfilled, just like they have more give than they otherwise should, almost like the internal leaves are a bit damp. The foot has an aroma that reminds me of a fruity tea, with the scent leading me toward red apples, peaches and blueberries at first. Old lumber, tea leaves and dried tobacco follow behind that, with a dry creaminess rounding things out. Two of the three cigars smell like they have had something done to them, while one is a bit more traditional in its aroma. I don’t get any appreciable amount of pepper from the feet of the three cigars. Air moves well on the cold draw, with the flavor a bit less vibrant than the aroma was, showing a subtler, thicker version of that fruit tea sensation. I thought that would be it, but as soon as I take the cigar out of my mouth, I find that the cigar has a very sweet head, though the intensity dials back a bit with each subsequent taste. It’s a bit fruity and reminds me of grape bubble gum at first, though given how long it has been since I’ve had bubble gum, I’m not sure that’s completely accurate, and the fruitiness varies from cigar to cigar. All three of the cigars have the unmistakable taste of a sweetened cap, leaving no doubt that there’s more going on than just tobacco.

As should come as no surprise, the first puffs of the Deadwood Tobacco Co. Chasing the Dragon Midnight Oil 54 x 6 1/4 have berry sweetness, reminding me of the juice from a bag of mixed berries, and occasionally with a bit of condensed milk sweetness mixed in as well. The tobacco has a touch of edge in the first puffs that cuts right through that, a flavor that seems to be common among cigars that get this or a similar treatment. My first retrohale offers a good bit of black pepper, which provides both a contrast to the flavor and some more traditional cigar sensations. I can already sense the effects of the steeping beginning to subside by the one-inch mark, either because it actually is subsiding or I’m just more acclimated to it, but the sweetened cap lingers to remind me. Likewise, one cigar has fresh red grapes in the retrohale that catch my attention for their brightness and for being the most natural smelling or tasting sensation thus far. After my palate adjusts to the flavor in the first half-inch or so of puffs, I find that it’s a fairly enjoyable if not traditional profile, marked by some raspberry and tons of creamy smoke, and outside of the sweetened cap, whatever the steeping process is adding is far from obtrusive. Flavor is medium, maybe medium-plus in intensity, body is a fairly creamy medium, and strength is mild, though I’m curious if the steeping process might result in a slightly different physical sensation. Construction is good on the whole, though the ash can be a bit flaky and fragile. The draw, burn line and smoke production are all very good.

There is still some sweetness to the profile as the Deadwood Tobacco Co. Chasing the Dragon Midnight Oil 54 x 6 1/4 gets into its second third, though the vast majority seems like it’s coming from the sweetened head of the cigar. Incorporating a retrohale or two helps to push that aside by way of dry lumber, some light pepper and a bit of creaminess. One cigar leans a bit more into the creaminess than the others do, and it helps to soften the flavors, making them accents more than drivers at times, avoiding something that I’ve found leads other cigars of this ilk astray. Just shy of the midway point, the cigar seems to have arrived at an ideal balance, holding onto enough of the steeped accents to make them known but not dominating the profile with them. Depending on the puff, this balancing brings out a bit of apricot and peach, with neither being too dominant. This new, balanced profile carries through the rest of the second third, keeping the cigar flavorful and enjoyable, though combustion steadily becomes an issue and the cigars need either a faster puffing rate or relights, leading me to wonder if the steeping process has added moisture that has not yet evaporated.

I mentioned that there were some rougher tobacco notes in the first puffs of the cigar, and they seem to return at the start of the final third. It’s a bit woodier than it was earlier, but the way in which the finish hits my taste buds and throat is pretty similar. I don’t know if the increasing need for relights is helping anything, but I can’t imagine they are. The Deadwood Tobacco Co. Chasing the Dragon Midnight Oil 54 x 6 1/4 isn’t dominated by harshness and does a pretty admirable job pushing it out of the profile before long, bringing back the sweet creaminess with its berry accents, specifically some blackberry with a light tea note behind that. While I don’t drink fruit-infused tea these days, this does seem like a flavor I have tasted in the past. I’m surprised to still be getting some the sweetened cap’s flavor as the band comes off, as it seems like it would have dissipated by now. Retrohales in the final third have more pepper than they have to this point, and taking one or two spreads the sensation of black pepper down to my taste buds, which is fascinating since I haven’t tasted much in the way of pepper by puffs alone. Combustion issues make getting all the way to the end of the cigar a challenge, but after more than three hours for each cigar, I’m not complaining about being shortchanged. Flavor finishes medium-plus, body is medium-full, and strength is medium-minus. Were it not for combustion issues, construction would be much better, though I would like the ash to be more durable.

Final Notes

• “Chasing the dragon” is a reference to “inhaling the vapor from a heated solution of a powdered psychoactive drug on a sheet of aluminum foil,” according to Wikipedia.
• Additionally, it can mean trying to recreate the high of one’s first experience with a drug.
• The abbreviations for Deadwood Tobacco Co. (DTC) and Chasing the Dragon (CTD) are inverses of each other.
• The right side of the band has Chinese characters on it, and when I ran them through Google Translate using my phone’s camera, I got both Chasing the Dragon and Chasing Orchids.
• Since we’re talking about definitions, to steep, in this instance, means to soak (food or tea) in water or other liquid so as to extract its flavor or to soften it.” as well as to “soak or saturate (cloth) in water or other liquid” according to Oxford Languages.
• If you look closely, you’ll see the Asylum skull logo repeated in the background of the main band.
• The tissue paper band was affixed very snugly, so much so that I could not slide it off or even attempt to slide it off without running the risk of damaging the wrapper leaf. It’s best to just remove the SKU sticker, or tear around it, before trying to remove that covering.
• I am intrigued by the lack of cellophane on these cigars, as it would seem a good idea not just for the protection of the cigars but also to help keep some of the steeping process in the cigars.
• I would be fascinated to try this cigar without the sweetened cap, as I found that to be far too dominant for my palate. I also don’t quite understand what the benefit is beyond sweetness being a familiar and comforting flavor.
• For an academic look at why humans—and many other animals—like sweet things, I’d suggest this article from Oxford University Press.
• I didn’t get any appreciable strength from the Deadwood Tobacco Co. Chasing the Dragon Midnight Oil 54 x 6 1/4. There are some moments when it felt like something was about to hit my system, but it never materialized.
• The cigars for this review were purchased by halfwheel.
• Final smoking time was three hours and 15 minutes on average.
• Site sponsor Cigars Direct carries the Deadwood Tobacco Co. Chasing the Dragon Midnight Oil 54 x 6 1/4, though it is out of stock at the moment.