Penelope Bourbon is taking its annual Cigar Sessions series to a bolder place with the release of Cigar Sessions: Chapter 2, a high-proof American whiskey crafted in collaboration with renowned cigar-makers Alec Bradley. 

The new expression brings together Penelope’s blending skill and Alec Bradley’s decades of cigar making experience to create a whiskey specifically designed to complement medium to full bodied cigars. 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. 

“Whiskey and cigars have always been an iconic pairing, built around the same appreciation for craft, patience and ritual,” Michael Paladini, founder and vice president of strategy at Penelope Bourbon, said in a news release. “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.” 

“A full-bodied cigar needs a whiskey that won’t back down from it,” Alec Rubin, brand manager of strategic partnerships at Alec Bradley, added. “Working with Penelope’s blending team from the start let us build something bold without either one overpowering the other.” 

Bottled at 117.4 proof and aged six years, Cigar Sessions: Chapter 2 features a mash bill of 69% corn, 19% rye and 12% malt. 

“Chapter 2 was an exciting collaboration between cigar and whiskey blenders,” Danny Polise, founder and master blender of Penelope Bourbon, said. “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.” 

The partnership brings together two brands with family woven into their stories from the start. Penelope Bourbon was named after Michael Paladini’s daughter, while Alec Bradley was named for founder Alan Rubin’s sons, Alec and Bradley. That shared connection adds a personal dimension to a partnership rooted in shared passion for craftsmanship. 

“Family has always been at the heart of Alec Bradley, so it’s especially meaningful to be partnering with a brand that carries that same spirit,” Bradley Rubin, brand manager and ambassador at Alec Bradley, said. “Bringing our two teams together on Cigar Sessions: Chapter 2 felt like a natural fit. We share a deep respect for the craft behind what we make, and we’re excited to see how that shared passion comes through in the pairing.” 

Penelope Bourbon Cigar Sessions: Chapter 2 (SRP $79.99) is currently available for purchase at select retailers nationwide while supplies last. 

Read more: Penelope Bourbon Launches New Classic Series

About Penelope Bourbon 

Founded in 2018, Penelope Bourbon has become one of the fastest-growing award-winning premium whiskey brands. The brand includes the Cooper Series, Limited Releases and Estate Collection. For more information, visit PenelopeBourbon.com.