This post sponsored by the Glencairn Whisky Glass

Five Brothers Bourbon is Heaven Hill’s newest release. It is a label that honors the five Shapira brothers who founded Heaven Hill Distillery. It is made from five different ages of Bourbon from 5-9 years of age. One year for each of the brothers. This new expression was introduced at the ribbon cutting ceremony for the Bourbon Heritage Center expansion in June 2021. 

Readers from Owensboro are going to say “wait a minute, Five Brothers was a Medley brand named after the five Medley brothers and their distillery!” Yes, that is true, but in 1992 Medley Brothers and their labels became part of United Distillers. In 1993, United Distillers sold the Medley brands to Heaven Hill and this label was part of that sale. Once again, Heaven Hill has prevented an old label from disappearing from the market completely. Heaven Hill has perfectly re-imagined this historical brand.

Five Brothers Bourbon

Proof: 90

Age: No Age Statement – No age statement is necessary since it contains Bourbons 5-9 years of age. It is technically considered a five years old Bourbon.


  • Mike: Caramel and orchard fruits – pears and apples, with a little sweet oak wood.
  • Matt: Caramel, pears and apples with a little oak.


  • Mike: Caramel and apples with some ginger spice and oak. Tasted with a dried cranberry and vanilla and citrus come forward to join the party. Tasted with a pecan and it becomes full of fruit with apples, citrus and dried fruit – apricots and prunes.
  • Matt: Caramel corn and apples with a little oak. The dried cranberry brought out notes of vanilla and orange cream. The pecan brought out notes of apples and grapes with a hint of lavender. 


  • Mike: Oak and ginger spice with a hint of floral white pepper. The dried cranberry made the finish very dry with lots of oak tannins. The pecan made the finish very long with notes of chocolate and oak.
  • Matt: Hot pepper jelly and sour apples. The dried cranberry brought out cinnamon spice and oak tannins. The pecan brought out notes of apple and chocolate.

I would pair this Bourbon with my pipe. A little Kremer’s Black Royal with its notes of coffee, chocolate and rich tobacco would complement the flavors in this Bourbon quite well.

Photos Courtesy of Rosemary Miller