On February 13, 2026, country music paused to remember Waylon Jennings, who passed away 24 years earlier in 2002 at his Arizona home due to complications from Type 2 diabetes. For fans, the date marks the loss of one of the founding architects of outlaw country. But for Struggle Jennings, it marks something even more personal — the anniversary of losing the man he called “Paw Paw.”
Taking to Instagram, Struggle shared a moving tribute. One image showed him kneeling beside Waylon’s grave. Another captured a tender family moment: Waylon with Struggle’s young daughter, while Jessi Colter looked on. The photos weren’t staged publicity shots — they felt intimate and deeply personal.
“Rest in peace Paw Paw.. 24 years later and I can still hear your voice,” Struggle wrote. “I still use your advice and I’m still down here trying to make you proud! I love you!”
Born William Harness Jr., Struggle Jennings grew especially close to Waylon after the tragic murder of his biological father in 1990. In interviews, he has spoken openly about how Waylon stepped in as a father figure during formative years.
“He taught me about family… about standing your ground… about sticking to your guns,” Struggle once shared. “He taught me what being a man is.”
Those lessons echo loudly in Struggle’s own career.
Launching his music path in 2002 — the same year Waylon died — Struggle carved out a hybrid sound blending country roots with hip-hop edge. Like his grandfather, he has lived through public struggles, including incarceration on drug-related charges before rebuilding his life and career. His collaborations with Jelly Roll and the release of albums under the “Waylon & Willie” banner were clear nods to the outlaw lineage that shaped him.
Waylon Jennings, born June 15, 1937, near Littlefield, Texas, built his legacy by challenging Nashville’s rules. As both a solo artist and member of The Highwaymen, alongside Willie Nelson, Kris Kristofferson, and Johnny Cash, he demanded creative freedom and reshaped country music forever.
But beyond the legend, beyond the outlaw persona, he was a grandfather who offered guidance, discipline, and love.
Twenty-four years later, Struggle’s words remind us that legacy is not just measured in hit records or Hall of Fame plaques. It is measured in advice passed down, in values taught, and in voices that linger long after they’ve gone quiet.
And for Struggle Jennings, that voice — steady, deep, unmistakable — still speaks.