Penelope Bourbon's Cigar Sessions: Chapter 2 Is Built Different — and the Alec Bradley Partnership Proves It
When Penelope Bourbon launched its Cigar Sessions series in June 2025, the concept was clear enough: craft a whiskey from the ground up with the express purpose of pairing alongside a cigar. Not just a marketing angle, not a label slapped on an existing release — an honest-to-goodness functional pairing designed in collaboration with people who actually make cigars for a living. That first chapter earned its share of attention and set the stage for an annual series with momentum. Now, with Chapter 2 arriving in fall 2026, the St. Louis-based brand isn't just continuing the series — it's escalating it in every measurable way.
Penelope Bourbon has teamed up with Alec Bradley Cigars for the second installment of its annual Cigar Sessions whiskey series. The collaboration signals a meaningful evolution in how the brand is approaching this project — moving from working with boutique cigar blenders to bringing in one of the most recognized names in premium American cigar culture. The resulting whiskey is harder, higher-proof, and deliberately bolder than its predecessor, the kind of bottle that doesn't whisper but carries its weight with intention.
From Chapter 1 to Chapter 2: How the Series Has Grown
Understanding what makes Chapter 2 a genuine step forward requires a look at where the series started. Penelope Bourbon aimed to elevate the classic pairing of whiskey and cigars with the debut of Cigar Sessions Chapter 1, the first release in the annual Cigar Sessions, with future chapters designed to explore a range of cigar pairings. It was an ambitious opening statement — not just a product launch but a declared intention to build out an entire category of pairing-specific whiskeys.
The blend of American whiskeys featured in Cigar Sessions Chapter 1 — Straight Bourbon, 100% American Single Malt, and American Light Whiskey — results in a profile developed specifically to enhance the enjoyment of medium-bodied cigar pairings. Made in small batches and aged six years with a mash bill of 72% corn, 15% rye, and 13% malt, Penelope Cigar Sessions Chapter 1 was bottled at 101 proof. That three-whiskey blend was genuinely unusual — American Light Whiskey is not a component that shows up in this corner of the market with any regularity — and the approach of mixing whiskey categories rather than staying within a single style gave it textural character that a straight bourbon alone wouldn't deliver.
The new addition to Penelope's Limited Releases expressions was crafted in collaboration with cigar blenders Cynn Coburn of Dissident Cigars and Lee Marsh of Stolen Throne Cigars. These were independent craftspeople operating in the boutique cigar world, and the partnership with them reinforced what Penelope was trying to accomplish: actual input from people whose livelihood depends on understanding how tobacco behaves on the palate. Danny Polise, Penelope Bourbon founder and master blender, explained that the development process was extensive: "We explored 19 various mash bills with the cigar blender team trying countless blend combinations." That's not a marketing embellishment. Nineteen mash bills is a serious research process, the kind of thing that takes months of iterative blending and tasting sessions.
A limited allocation of 7,500 cases was available in select markets, with a minimum suggested retail price of $79.99 per 750mL bottle. The size of the allocation gave it enough reach to generate real consumer feedback without flooding the market — a strategic call that has clearly informed how the team approached Chapter 2.
What Chapter 2 Brings to the Table
The Specs: Higher Proof, Different Grain, Different Beast
Cigar Sessions: Chapter 2 is a six-year-old American whiskey bottled at 117.4 proof, with the blend developed specifically to pair with medium to full-bodied cigars. That proof jump from Chapter 1's 101 is not incidental. Moving from 50.5% ABV to 58.7% ABV changes the fundamental character of a whiskey — it brings more heat, obviously, but it also carries more barrel extract, more spice intensity, and a longer finish. All of those qualities matter when you're trying to hold your own against a full-bodied smoke that can easily overwhelm a lighter pour.
The full spec sheet reads: Chapter 2, 117.4 proof, 58.7% ABV, 750mL, cask-strength American whiskey, with a mash bill of 69% corn, 19% rye, and 12% malted barley, non-chill filtered, bottled by Penelope Bourbon Bottling Co. That rye content — climbing to 19% from Chapter 1's 15% — adds backbone and pepper character without tipping into a full high-rye profile. The corn stays dominant, keeping the sweetness structure intact, while the malted barley rounds out the grain complexity. Non-chill filtration is the right call at this proof level; stripping fats and fatty acids from a 117-proof whiskey would be counterproductive, and keeping them in the bottle means the mouthfeel is as substantial as the heat suggests it will be.
On the nose, the whiskey opens with toasted oak, caramel, vanilla, baking spice, roasted grain, and a subtle tobacco sweetness. The palate delivers rich caramel, seasoned oak, pepper spice, toasted malt, brown sugar, and warm barrel character. That tobacco note on the nose is particularly interesting — whether it's an artifact of the oak interaction at cask strength, or a deliberate outcome of the pairing-focused development process, it creates an aromatic bridge between the glass and whatever cigar sits in the ashtray next to it. The finish is long and warming, with lingering spice, oak, caramel sweetness, and a cigar-friendly depth.
The Development Process: Built Together, Not Just Labeled Together
The most important distinction between Chapter 2 and the wave of whiskey-cigar crossover products that have populated the market in recent years is how it was actually made. Unlike simply attaching a cigar brand to the release, Penelope's blending team worked with Alec Bradley's cigar blenders throughout the development process. That's a real difference. Licensing a name for a label is one thing. Having cigar blenders at the tasting table while the whiskey blend is being dialed in is another thing entirely.
Polise described the iterative nature of the process in direct terms. "Chapter 2 was an exciting collaboration between cigar and whiskey blenders," said Danny Polise, founder and master blender of Penelope Bourbon. "We would adjust the blend, taste it alongside the cigars, get the Alec Bradley team's feedback and keep dialing it together. That process helped us find the right balance of proof, depth, and flavor so the whiskey could stand up to a fuller-bodied cigar without either one overpowering the other."
That phrase — "without either one overpowering the other" — is the central engineering challenge of any serious whiskey-cigar pairing. Too light, and the cigar turns the whiskey into a background note you barely register. Too aggressive, and the whiskey flattens the tobacco's complexity. The target is a dynamic where each element enhances what the other is doing — where the pepper in the rye amplifies the spice in the tobacco, where the caramel of the barrel softens the cigar's bite, where the finish of both converge into something that exceeds either one standing alone.
Michael Paladini, Penelope's founder and vice president of strategy, framed the ambition behind the collaboration with characteristic directness. "Whiskey and cigars have always been an iconic pairing, built around the same appreciation for craft, patience and ritual," Paladini said. "With Chapter 2, we wanted to take that classic pairing a step further by bringing the people behind both to the table. The goal was to create a whiskey purpose-built for a smoke, and the Alec Bradley team brought the same obsession with craft that we bring to blending whiskey."
Alec Bradley: A Family-Built Brand With Real Industry Credibility
The choice of Alec Bradley as a collaborator for Chapter 2 carries weight beyond name recognition. Alan Rubin started an obscure cigar company named after his two sons and almost went bust before the turn of the millennium, but once he was able to partner with the right people and secure the right tobaccos, Alec Bradley Cigar Co. went from an unknown maker of mediocre smokes to an established name in the premium cigar industry. That story arc — from near-failure to industry credibility through sheer product refinement — mirrors the kind of tenacity that serious enthusiasts respect.
A high-water mark for Alec Bradley came in 2011, when the beloved Prensado line claimed the top spot on Cigar Aficionado's Top 25 list. In the intervening years, Alec Bradley would develop a wide range of exciting cigars, including Black Market, Magic Toast, and Project 40. Cigar of the Year from Cigar Aficionado is roughly the equivalent of a double gold at the San Francisco World Spirits Competition — it carries real institutional weight, the kind that doesn't come from marketing spend alone. It comes from the tobacco.
Alec Bradley is the name of a popular brand of handmade cigars established in 1996 by Alan Rubin. Rubin launched the brand, named after his children, at the tail end of the cigar boom of the 1990s and entered a clogged market. Three decades later, the brand has expanded from its original identity into a full family enterprise. In the mid-2010s, Alan Rubin began to give his sons, Alec and Bradley, greater roles at the company. Today the Rubin family runs what amounts to a generational institution in premium cigars, and that accumulated expertise in tobacco blending is exactly what Penelope was tapping into for Chapter 2.
There is also the matter of the Alec Bradley Uncut Series, which was already building a relationship between the two brands before Chapter 2 was announced. Alec Bradley unveiled a release in its limited Uncut Series, partnering with Penelope Bourbon for a highly exclusive cigar-and-whiskey pairing. The release brought together two Alec Bradley Do Not Disturb Robustos and a 750ml bottle of Penelope Bourbon Estate Series Single Barrel, marking the eighth installment in the Uncut Series and the first collaboration with Penelope Bourbon. That prior working relationship meant that when Penelope came to Alec Bradley to develop Chapter 2, both teams already understood how the other thought about craft. Chapter 2 isn't a cold collaboration — it's a deepening of something already started.
A Shared DNA: Two Brands Named After Someone's Kids
One of the more quietly interesting aspects of this partnership is the biographical symmetry between the two brands. The collaboration has a family connection between the two brands: Penelope Bourbon was named after founder Michael Paladini's daughter, while Alec Bradley takes its name from company founder Alan Rubin's sons, Alec and Bradley. Both brands were built by men who cared enough about what they were making to put their children's names on it. That's not a minor detail — it speaks to the kind of personal investment and identity that shapes how a company operates, the corners it doesn't cut, the pride it takes in individual releases.
Founded in 2018, Penelope Bourbon has become one of the fastest-growing award-winning premium whiskey brands, offering a range of uniquely blended and finished straight bourbon and whiskey expressions known for their smoothness and rich flavor, and premium handcrafted ready-to-serve cocktails. The brand's growth trajectory has been sustained by a consistent willingness to push category boundaries — using American Single Malt when that style was still being largely overlooked by the bourbon crowd, leaning into creative finishing and blending rather than chasing age statements as the primary value proposition. The Penelope Core Series expressions have won more than 40 spirits industry awards, including double platinum at the 2024 ASCOT Awards and double gold at the 2024 San Francisco World Spirits Competition for Barrel Strength.
The Industry Context: Why Cigar-Whiskey Pairings Are Serious Business Now
The concept of designing a whiskey around a cigar is not new, but it has historically been executed with varying degrees of commitment. For most of the past decade, "cigar blend" on a whiskey label was shorthand for something sweet, approachable, and broadly inoffensive — a whiskey that wouldn't clash with a cigar, as opposed to one engineered to complement it. The term "cigar blend" is undefined, and as a result, has different meanings to different drinkers and companies. As the name suggests, it is typically meant to be paired with a cigar, but it has become more than that over the years. The vagueness of the category has allowed some brands to coast on the association without doing the actual work.
Penelope's Cigar Sessions series is a direct challenge to that low-effort approach. By bringing actual cigar blenders — not consultants, not advisory board members, but practicing craftspeople actively shaping the blend — into the development process for both chapters, the brand is making a functional argument: that the pairing is the product, and the product was built around the pairing. Cigar Sessions: Chapter 2 was developed as a true collaboration, with Penelope's blending team and Alec Bradley's cigar blenders working together from the start. The result is a whiskey purposely built for a smoke, with the depth and intensity to stand alongside a bolder cigar while maintaining the balance and complexity that define Penelope Bourbon.
That word — "purposely" — is doing real work in that sentence. Purposely built implies that choices about proof, mash bill, filtration, and flavor development were all made with the cigar in mind at every decision point, not retrofitted with a pairing suggestion at the end. That's a higher bar, and Chapter 2's 117.4 proof is perhaps the clearest evidence that the team was willing to make decisions that serve the pairing even when they complicate the product's standalone accessibility. A cask-strength whiskey demands more from the drinker — requires slower sipping, possibly a few drops of water, and active engagement rather than passive consumption. That's exactly the mindset that a long cigar session rewards.
What the Whiskey Actually Tastes Like in Context
The tasting notes for Chapter 2 read like they were designed for the pairing environment. The nose opens with toasted oak, caramel, vanilla, baking spice, roasted grain, and subtle tobacco sweetness. The palate brings rich caramel, seasoned oak, pepper spice, toasted malt, brown sugar, and warm barrel character. The key flavor vectors here — pepper, oak, caramel, tobacco — are precisely the elements that create harmonic resonance with a medium-to-full-bodied cigar rather than competing against its earthiness or leather.
The jump in rye content from Chapter 1's 15% to Chapter 2's 19% is audible on the palate, particularly in that pepper spice note. It gives the whiskey a drier, more assertive midpalate that doesn't collapse under the weight of a fuller smoke. At the same time, 69% corn ensures that the sweetness base is solid — caramel, brown sugar, and vanilla provide the counterbalance that keeps the whiskey from turning bitter when it meets the tannins in tobacco. Adding a few drops of water is said to open the oak, caramel, and spice notes further — a useful option for those who want to push the whiskey's aromatic complexity to the foreground while working through a longer smoke.
Compare those characteristics to Chapter 1's profile, which opens with notes of milk chocolate, vanilla, and candied apple on the nose, with chocolate, dried peach, tobacco, and warm caramel on the palate, and a finish of toffee, dark fruit, and light oak. Chapter 1 was built for the medium-bodied cigar experience — softer, rounder, with more fruit and confectionery notes. Chapter 2 trades some of that softness for intensity. The fruit notes dial back, the oak becomes more pronounced, the heat is more present. It's a deliberate evolution, calibrated to pair with a heavier smoke rather than simply producing a crowd-pleasing whiskey with a cigar on the label.
Availability and Pricing
Penelope Bourbon Cigar Sessions: Chapter 2 is priced at $79.99 and is now shipping to select retailers nationwide. The price point matches Chapter 1 exactly, which matters in a market where cask-strength releases regularly clear $100 without blinking. Holding the price at $79.99 for a 117.4-proof, non-chill-filtered, six-year whiskey developed through a genuine cross-category collaboration is a defensible value proposition — it costs the same as the gentler first chapter but delivers significantly more whiskey in the traditional sense of what that means: more barrel intensity, more proof, more of everything that makes a long sit on the porch with a serious cigar feel like time well spent.
The limited-release nature of the series means availability will vary by market. Cigar Sessions Chapter 1 joined Penelope's celebrated Limited Releases lineup, which also includes American Light Whiskey, Toasted Rye, and F*ck Cancer — offerings that showcase the brand's commitment to blending innovation and rare barrel selections. Chapter 2 joins that same lineup, which means buyers who are already plugged into the Penelope ecosystem will know to move quickly when it lands on shelves locally.
Looking Ahead: What the Cigar Sessions Series Signals
Two chapters in, the Cigar Sessions series is already one of the more coherent product stories in the limited-release American whiskey space. Most annual series chase some form of variation for its own sake — different finishes, different barrel types, different age statements — without a clear conceptual through-line connecting each release. Penelope's series has a through-line built into its DNA: each chapter is a functional pairing product, designed with practicing cigar blenders, calibrated to a specific body weight of smoke, and released at a proof and profile that serves that purpose.
The logical question is where Chapter 3 goes. Chapter 1 targeted medium-bodied cigars at 101 proof. Chapter 2 targets medium-to-full-bodied at 117.4 proof. The natural next move would be something aimed squarely at the fullest end of the cigar spectrum — Maduros, big Robustos, heavily pressed parejos with dense, heavy tobacco that demands a whiskey with real structural presence. Whether that means more proof, more rye, or a different grain architecture entirely remains to be seen. But if the development rigor that produced Chapters 1 and 2 continues, the outcome should be worth the wait.
What Penelope has established with this series is something more valuable than a single successful product: a credible methodology for cross-category collaboration that produces results you can taste rather than just describe. The partnership with Alec Bradley — a brand built over three decades of hard-won credibility in premium tobacco — gives Chapter 2 a co-signer whose expertise is proven and whose standards are publicly documented. For the man who likes to spend a Saturday afternoon on the patio with a serious cigar and a glass of something worth thinking about, Chapter 2 is not just a release worth finding. It's a case study in what happens when two industries with parallel traditions of craft, patience, and obsessive refinement decide to stop running parallel and start working together.
