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'21 Strong: Meet 'Mr. Some Kind of Wonderful'

After decades on the streets and wrapped up in drugs, Dennis Ashton turned his life around, only to have his past catch up with him in the most remarkable way.

CLEVELAND — We are coming off a year that's been hard on people from all walks of life, but those battling addiction and housing instability have faced even greater challenges.

One man is there ready to help them face their challenges. His own troubled past paved the way for this role, his life's greatest work. 

His name is Dennis Ashton, but as you will soon learn, around Cleveland he is also "Mr. Some Kind of Wonderful."

From his teens until turning 50, Ashton owned the streets of Anacostia Southeast. The small wedge of Washington, D.C. is going through a rebirth, but back in Dennis' days it was called the "Forgotten City."

Credit: Dennis Ashton
Dennis grew up in a loving home, but says the pull of the streets was powerful. He battled drugs and at times, homelessness. "I came to Cleveland to get sober," Dennis said.

"That was where everything [was] you didn’t want: the low-income hospital, the jail, sewage treatment plant," he remembers. "Nothing was there but projects, and that’s where I grew up."

His childhood home was a stark contrast to the poverty, pollution, and crime of Anacostia. His hardworking parents were devoted to their children and provided a good home. Yet with all the love, they couldn’t compete with the forces that pulled Dennis to the streets and held him for 26 years.

"[It was] where money was a thing, riding around in pretty cars and dressing real nice and all that, you know what I am saying?" he shared. "And from there I went to Anacostia High School, got a little older, and that’s when I got into drugs, very heavy. You don’t care about anybody, even your family, and I know my family went through it. I never realized how bad I was hurting them."

Credit: Dennis Ashton
Dennis knows he put his parents through a terrible time. "You don't care about anybody, even your family. And I know my family went through it. I never really realized how bad I was hurting them."

Watch the story that first introduced us to Dennis Ashton

It went on until one day Dennis decided he’d had enough.

"I was just sick and tired of being sick and tired," Dennis said of doing drugs and living on the streets. "It was the worst place in the world. If there ever was a Hell, that was Hell."

To escape "Hell," Ashton headed west, bound for the city of his football hero, Jim Brown.

"I came to Cleveland to get sober," he said.

Cleveland gave Dennis a fresh start and distance from his troubled past. He worked in construction, building a new life and reaching retirement.

That's when his past eventually caught up with him, is the most divine way.

"I didn’t forget the people where I came from," he told us. "I wanted to give them what I got, so that is how I got to be an outreach worker and working with the homeless."

Ashton is part of the invaluable team at the Northeast Ohio Coalition for the Homeless, where he answers the call for help at all hours.

"By the time I get in my car at 7 in the morning, my phone is ringing," he says. "If they are on drugs and you want to detox, we are going to detox today. I’m not going to say 'I’m calling you tomorrow.'"

Credit: Dennis Ashton
"I think from the day I was born, this was my pathway to purpose. I couldn't have learned this in school. Went to college. I could have got a doctor's degree in homelessness. It couldn't have taught me any better how to deal with people than what I've learned, being in the streets."

Whether its finding housing, a place to rehab, or just providing a warm pair of socks, ever day is a good day for Dennis.

"I think from the day I was born, this was my pathway to purpose," he said. "I couldn’t have learned this in school. I could have gone to college, gotten a doctorate degree in homelessness and it couldn’t have taught me any better how to deal with people than what I’ve learned being in the streets."

And that feeling when he succeeds in helping someone is undeniable.

"It’s wonderful," he gushed. "It’s some kind of wonderful."

We couldn’t agree more; it IS some kind of wonderful. This '21 Strong hero found his life's true purpose here in Cleveland, serving with grace and giving hope to those who need it most.

"I’m doing God’s work," Dennis said, later laughing. "When he’s finished with me doing his work, then I guess I’ll go off to Heaven or somewhere. I don’t know, it probably won’t be Heaven. Maybe Anacostia, or something."

Dennis and the rest of Team NEOCH could use some help these days. The pandemic has made their job even more challenge. Find out how to help Team NEOCH HERE. 

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