As Thanksgiving approaches each year, many families gather around the table to reflect on gratitude, love, and the people who matter most.
For Jessi Colter, Thanksgiving carries a deeper, more personal meaning.
It was on Thanksgiving Day in 2001 that her husband of more than three decades, Waylon Jennings, made a decision that forever changed his heart.
From Preacher’s Daughter to Outlaw’s Wife
Jessi grew up in Arizona, the daughter of a Pentecostal minister. By 11, she was playing piano in her mother’s church. Faith was woven into her childhood.
When she met Waylon in the 1960s at JD’s nightclub in Phoenix, she had drifted from that faith. On their first date — a long drive through the Painted Desert — they talked about religion. Waylon remembered “fire and brimstone” sermons from his youth that pushed him away from church. Jessi told him her experience had been different — love, not fear, was the message.
They married in October 1969 and moved to Nashville, becoming central figures in country music’s outlaw movement. Their life was electric, creative, and often chaotic.
And it was far from perfect.
The Battle With Addiction
Waylon’s struggles with amphetamines and cocaine are well documented. Jessi loved nearly everything about him — his humor, his stage presence, his sincerity — but she could not abide his addiction.
She considered staging an intervention, like the one that helped Johnny Cash. But in her heart, she felt it wouldn’t work for Waylon. He had to choose sobriety himself.
So she prayed. And waited.
In March 1984, Waylon made that choice. They retreated to a rented house in the Arizona desert. He quit cold turkey. The withdrawal was brutal. But he did it — and remained sober for the rest of his life.
Jessi later emphasized that his method was not a model for others. It was dangerous, painful, and deeply personal. But for him, it worked.
The Toll of the Past
Even after sobriety, the years of hard living had taken their toll. Diabetes, heart problems, surgeries — the body keeps score.
In their later years, they moved back to Arizona. Waylon could no longer drive because of pain in his legs, and Jessi would take him to their favorite desert spots. He spoke openly of regrets.
“I did foolish things,” he told her. “I hurt people.”
“God is forgiving,” she replied.
“God may be,” he answered quietly, “but I’m not.”
Thanksgiving 2001 — The Conversation
On Thanksgiving Day in 2001, Waylon was in the hospital. Jessi felt in her spirit that the time had come to ask the question she had carried for years.
From his hospital bed, he sensed it.
“Looks like you want to say something to me, darlin’,” he said.
She asked him plainly:
“Are you ready to accept the Lord? Are you ready to be God’s man?”
He smiled. “I knew you were going to ask that.”
Then he asked what he needed to say.
Jessi told him: accept Jesus, love Him, and turn your life over.
Waylon said the words.
She wept.
He took her hand and said, “I love you so much.” She had heard those words countless times before — but this time they were softer, more vulnerable, filled with peace.
Jessi later described it as a new kind of confidence. Not the swagger of an outlaw superstar. But the quiet assurance of someone who knew he was “God’s man.”
The Final Months
That Christmas, surrounded by family, Waylon asked Jessi to play the hymns she had learned as a girl. Despite oxygen tanks and medical equipment, there was calm.
His health did not improve. On February 13, 2002, Jessi found him unresponsive at home. Paramedics could not revive him.
He was gone.
But not entirely.
A Love That Endures
Jessi once admitted she had nearly left him during his darkest days. Addiction nearly destroyed everything. But something told her to stay. To believe. To trust that peace would come.
And it did — on Thanksgiving.
“No one is ever totally gone,” she has said. “We leave our mark on the world.”
Waylon left his through music.
Through the outlaw movement.
Through songs that still echo.
And through a marriage that, as Kris Kristofferson once called it, was a “beautiful love affair.”
This Thanksgiving, Jessi remembers not just loss — but redemption.