June 15, 2023 – I’ve been working my whole life to try and be the man I am today, up and down a lot of different roads,” Jennings says. “I was kind of a wild kid, got in a lot of trouble when I was young. I got in really a whole bunch of trouble when I was in Dallas. My brother wound up in prison. My mama said I needed to go out and live with my daddy. So I moved out to West Texas. That’s where I like to think I became a man. “Before that, I was pretty irresponsible, got in trouble with the law and all kinds of crazy stuff,” he adds. “It’s where I met my Uncle Beau, and the first thing he said to me is, ‘You got any boots, boy?’ He took me out, bought me a pair of work boots.”
Jennings worked on a cotton farm for about ten years, until his mother, Katherine, got sick, and he returned home to take care of her.
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