Like many bourbon brands, cigar companies are often family businesses that are kept alive or revived by determined relatives. We’ve seen this play out a lot recently in Kentucky with brands that were snuffed out by Prohibition being revived by family members generations away from the last relatives who owned or worked in a distillery. The same happens in the cigar industry with relatives bringing back lost brands after years of hearing family legends. One great example of this is La Palina.

Samuel Paley emigrated from Ukraine in the late 1800s and ended up in Chicago, Illinois where he started the Congress Street Cigar Company. La Palina was his flagship brand. He retired in 1926 and the brand was lost to time until his grandson Bill Paley brought the brand back.

For this bourbon and cigar pairing study in addition to Michael, Wayne, and me we invited a local Louisville Bourbon Hound to join us. J.J. Valentine is new to the cigar world and this was his first time studying pairing them with cigars.

His overarching opinion of the process: “One thing that was solidified that night is that a good cigar and bourbon with great company can make any night remarkable. The cigar you had me try had to be one of the best cigars I’ve had. As it got to the end I did not want it to be finished. This was my first experience with a v cutter and I was amazed at the difference.”

Four Roses Yellow Label – The smoke brings out oak and a fall apple orchard in the bourbon, while the bourbon brings out creaminess in the smoke.

Michter’s US1 Bourbon – The cigar brings out excess spice in this bourbon and deadens everything else. The bourbon makes the smoke grassy.

Early Times Bonded – The smoke brings out sweet allspice and leather in the bourbon, while the bourbon brings out chocolate in the smoke.

Henry McKenna 10 Year Bonded – The cigar makes the bourbon very sweet and fruity with pie spice, while the bourbon makes the smoke very chocolatey.

There were some surprising results here and I’m glad we worked some different bourbons into the rotation this time around. We all agreed that the Henry McKenna and Early Times were our favorites, but we disagreed about which order they came in. I personally liked the McKenna best while Wayne preferred the Early Times.

“The pairings we did to see what the bourbon did to the cigar and vice versa was quite and experience,” reports Valentine. “I enjoyed the Early Times Bottled in Bond and Henry McKenna Bottle in bond the most of the night. The cigar gave the Early Times Bottled in Bond a little more spice in the end and cut some of the sweetness I’ve experienced. The cigar also made the Henry McKenna more sweeter up front and emphasized the spiciness.”

I had commented right as we were getting started that we didn’t have a wheater in the lineup, and Valentine agreed with me that it would have been a nice one to add to the lineup: “After thinking more since I love wheat bourbons I wished we had paired a wheat bourbon with the cigar.”

So how was it for a first-timer to try our process? “This is something I will do in the future to see how things change with my favorite bourbons. I truly look forward to more pairings and if you ever need a seat filled let me know and I’ll come right over.”

You bet, J.J.!

Photos Courtesy of Maggie Kimberl