Transformation is at the heart of Struggle Jennings’ powerful story. This conversation begins where many legendary stories do: in the middle of a struggle. For Struggle, life has been a constant tug-of-war between the country music legacy he was born into and the outlaw world he found himself in.
Ten years after his release from prison, Struggle joins TURTZED to share a testimony of what happens when you stop running from your past and start using it to “refind” yourself. This isn’t just about music; it’s about the grit required to break generational cycles and the bravery it takes to look in the mirror and finally take full accountability.
Turning Pain Into a Testimony
One of the core motivations driving Struggle today is the refusal to let his past suffering go to waste. Having lost friends to gang violence and overdoses, and having served a long-term prison sentence himself, he views his life as a responsibility.
- Moving Beyond the “Badge of Honor”: In the “outlaw” world, bad decisions are often worn as a badge of honor. Struggle realized that using those same experiences as a testimony of overcoming is far more impactful.
- A Guide for Others: He acknowledges that his fans use his life and music as a guide for what they can accomplish.
- The Price of Failure: For Struggle, staying on the right path is a way to prove that the narrative “people can’t change” is fundamentally wrong.
The Breaking Point: Macaroni and Cheese
Transformation rarely happens without a moment of total surrender. For Struggle, that moment arrived during a phone call from a prison cell.
“I had to teach [my daughter] how to make macaroni and cheese over the phone so that she could feed her siblings… that was one of those moments that I was like, these babies are not going to make it… I’m the cause of this.”.
This visceral realization forced a shift from blaming “the judge” or “the snitch” to taking full accountability for his actions. He realized his “hand” in life wasn’t actually that bad—he just needed to learn how to play it better.
Defining True Resilience
While Struggle has survived high-stakes chaos, he defines true resilience through the eyes of his children. Even while he was incarcerated and their lives were in turmoil, they never lost hope that “Daddy was coming home and going to fix it all”.
The Legacy of the Fight
Today, his children aren’t just surviving; they are leading.
- Foster the Future: His daughter, Courtesy, started a foundation to support children aging out of foster care, inspired by her own time in the system.
- Breaking the Cycle: Despite a childhood that included drug houses and homelessness, Courtesy is now an honors student heading to Wofford College.
- The Mirror Test: Struggle emphasizes that real change only begins when you are honest in the mirror about what needs to be fixed.
Unapologetically Authentic Music
As the grandson of the legendary Waylon Jennings, Struggle was born into a legacy of anti-establishment thinking. He pioneered “Country Rap” by blending the storytelling of country with the raw struggle of hip-hop.
Whether it was filming the “Black Curtain” music video while literally inside a prison or sampling his grandfather’s old records, Struggle’s career is defined by a refusal to sugarcoat the truth.
The Message to Carry With You: “Clear Your Field”
Struggle leaves listeners with a powerful analogy shared by a friend in New Mexico: God is a farmer, but He doesn’t plant seeds in rocks and weeds.
- The Work of Preparation: Accountability means doing the hard work of pulling the weeds and digging up the gravel in your own life so you are ready to receive the harvest.
- The Bottom is a Foundation: Having been to the bottom numerous times, Struggle explains that he thrives when his back is against the wall because he refuses to quit until the buzzer rings.
“Don’t let your past define you. Make it refind you.”.
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