This episode is being re-released due to a significant growth in the audience since its original airing. It falls under the classic material series, intended to familiarize the listeners with the guest, Jr Boss, ahead of an upcoming event in Alabama on August 23. This episode is particularly special as Jr Boss is The Wolf of Wine’s best friend, marking their first performance together. Additionally, The Wolf of Wine discusses his new book.

In this episode, The Wolf of Wine sits down with Montgomery, AL rapper and street legend Jr Boss. The conversation spans from their shared upbringing in The Bronx to Jr Boss's survival through life-threatening situations and time in prison. Jr Boss shares his story of perseverance through dark times, drawing a parallel between his journey and the resilience of old vines in winemaking, which endure rough vintages to produce greatness, just like Jr Boss.