"After 40 years, I never went out and looked for another job so evidently this was meant for me to be," Jackson Sr. said.
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For four decades he's brought seniors the meals they need and started by working double shifts behind the wheel and in the kitchen before becoming solely a delivery driver.
"Ever since I was a kid I kind of took to old people listening though, because I like to say you learn from listening. So I always liked having conversations with my elders," he said.
Along the way, he's built relationships with hundreds of Chicago seniors who look to him for that hearty hello, a smiling face, and a moment of conversation.
"I told some, maybe a third of them because if I told all of them I'd never finish the route," Jackson Sr. said. "I'm behind now because everybody wants to say goodbye. A lot of them telling me stop by and visit sometime."
And now as Jackson Sr. is ready to go on the last meal routes of his career, his son Artha Jr. is ready to take the reigns of his dad's old route.
"I see all the love he gets and it really inspired me to be a better guy," Jackson Jr. said. "That's why I'm trying to take his place and hopefully be as good as he is."
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Artha Jackson Jr. grew up riding that route with his dad and says seeing him at work shaped the man that he's become.
"Just really proud that I can go and try to live up to him and I guess just be half of the man he is," he said.
The family affair is changing lives and making Chicago proud.
"I'm just hoping that he enjoys it and does a better job than what I did if possible," Jackson Sr. said.
"(I'm) happy to wake up Monday morning and get to work," Jackson Jr. said.
To support the Chicago Meals on Wheels Program or want information about services, head to mealsonwheelschicago.org.