Trouble in Blues: Celebrating 100 Years of Chicago Blues with Good Trouble's Kentucky Bourbon
- Jes Smyth
- Dec 19, 2025
- 4 min read
Updated: Dec 20, 2025

Good Trouble Bourbon is on a mission to spread meaningful impact beyond what's inside a bottle. Founded by Dee M. Robinson, a Chicago entrepreneur and social impact advocate, the brand's focus is not just on how the bourbon tastes but also on connections and the impactful conversations you can find when you "look for good trouble"—a phrase rooted in activism and positive change. Guided by this mantra, the brand donates a portion of the proceeds from Good Trouble bourbon sales to Shine Your Light Foundation, a nonprofit focused on equity, inclusivity, and community programs.
"Most brands only focus on what's inside the bottle, we're focused on what the bottle can inspire, since we know the bourbon is amazing."
Additional accolades should be noted for the brand's transparency, as it publicly discloses where its bourbon is sourced, a practice not often seen among smaller whiskey brands. The label includes the DSP number (DSP-KY-10), which is Green River Distilling Company, the 10th-oldest licensed distillery that entered its revival in 2020. I would also be remiss not to highlight Dee's perspective on bourbon, which many enthusiasts in the whiskey community would likely agree with: that bourbon can be a catalyst for conversation, connection, and positive social change.

The limited edition release, Trouble in Blues, is inspired by the soul of blues and the heart of Chicago. This bottle pays homage to some of Chicago's blues legends, including Buddy Guy, Muddy Waters, and Little Walter, who sparked a movement in music history. In the press release for Trouble in Blues, Robinson says:
With Trouble in Blues, we're raising a glass to the legends who paved the way—and inviting a new generation to honor the rhythm, resistance, and roots of this city. This bottle is our tribute to the sound that helped shape America.

As a Chicago-area native with a professional saxophonist brother, I was certainly intrigued when Good Trouble reached out with a media sample for Trouble in Blues. I want to thank the team at Good Trouble for introducing me to their brand and allowing me to taste the bourbon inside. As always, this review is in accordance with the ATW editorial policy, which I tasted before spending time researching the disclosed distillery source. So, let's sit back, dim the lights, and see what this glass of Trouble in Blues has to say, shall we?
Company on Label: Good Trouble Bourbon (sourced by Green River Distilling Company)
Whiskey Type: Kentucky straight bourbon whiskey
Mash Bill Percentages: 70% corn, 21% rye, 9% malted barley
Proof: 100°
Age: 5 years
MSRP: $169
Further Identification: This is a limited edition release with only 445 bottles, some of which are signed by Chicago Blues legend, Buddy Guy
Nose: I'm pleasantly greeted by a sweet, oily note as I lift the glass to my nose, accompanied by classic notes of vanilla and caramel, a melody that invites me to settle in and explore further. What I find, as I sit and swirl the liquid around, complements my expectations in an exciting way: raspberry compote, cherry syrup, vanilla wafers, and a soft dash of cinnamon and clove. Digging my nose deeper in, I notice a note often found on longer-aged whiskies: soft leather and old books. The longer I nose my glass, the more the foundation of classic bourbon notes builds into sweet fruits, turning more candied, like raspberry Tootsie Rolls, with just a touch of overripe strawberries. I think it's time for a sip! What I find after a few sips supports the oakiness in this pour, amplifying the once-subdued cinnamon notes into a more robust crack of black pepper. As I near the end of my tasting experience, the fruit and vanilla take a back seat, and notes of cereal come forward, a lovely welcome against the sweet and spice. The empty glass smells of honeycomb, cappuccino froth, and Hershey Kisses.
Palate: Oh, this is easy sipping—silk on my tongue with little to no heat. The flavors are gentle but cohesive and align with the nose: vanilla, caramel, sweet tarts, and maraschino cherries. There's a gentle ginger ale spice with a dash of cinnamon, not overpowering, but a nice balance to the sweetness. The finish is medium in length and leaves a lingering warmth in my throat. There is a slight drying sensation on my tongue as I swallow and let the flavors linger, but nothing off-putting. Additional sips reveal earthy undertones, steeped tea leaves, and hay, as vanilla, caramel, and cherry continue to champion my taste buds. My final sip is as easy as the first, a perfect companion on a cold winter's night, like the easy yet emotive music of the blues.
TL;DR: A delightful dram filled with all the notes one would expect from a well-composed bourbon
Rating: 4/5
Like listening to a blues song filled with expressive notes and lyrics, this pour mimics much of the same foundation. While it's not super complex, the flavors this pour offered demanded attention and are well-suited to the patient taster who can sit through a late set of expressive, unhurried notes. I'm impressed with my introduction to Good Trouble Bourbon and certainly have them on my radar for future releases.


