Three Chattanooga men serve as models for plotting a course through life after prison

Staff photo by Troy Stolt / JaMichael Caldwell, Joe Jenkins, and Tony Oliver pose for a portrait outside of Orchard Park SDA church on Tuesday, Feb. 9, 2021, in Chattanooga, Tenn. All three men were once incarcerated, and have since gone on to start their own successful businesses.
Staff photo by Troy Stolt / JaMichael Caldwell, Joe Jenkins, and Tony Oliver pose for a portrait outside of Orchard Park SDA church on Tuesday, Feb. 9, 2021, in Chattanooga, Tenn. All three men were once incarcerated, and have since gone on to start their own successful businesses.

The criminal justice system can be a vicious cycle from which it's hard to break free, and for three Chattanooga men, that path has been at times long and winding.

Each year in Tennessee, around 40% of the state's prison population is made up of people going or returning to prison for violating supervised release conditions, according to a 2019 study by the Sycamore Institute, a nonpartisan, Tennessee-based research institution.

Those conditions depend on the type of release, but they range from random drug screens to curfew checks and required completion of community service hours to required employment.

And while community supervision costs the Tennessee Department of Correction far less per individual than incarceration - $1,300 per person in 2017 versus $26,000 for incarceration, according to the study - about half of those released from prison return within three years.

That cycle is something Troy Rogers, Chattanooga's public safety coordinator, strives to stop.

As part of his job - and outside of it, too - Rogers has taken on the task of providing help and mentorship to men and women of all ages who are both at risk of falling into the criminal justice system and those who are working to get out.

"I think the formula for succeeding is having a successful reentry program while you're inside," he said. "I think we, as a community, have to go inside the gates and begin to work with them ... so day one, when they come out, they're able to be employed."

Tony Oliver, JaMichael Caldwell and Joe Jenkins are just three of the people he's helped.

And today, all three men are homeowners, have started their own businesses and are working to give back to the community in their own ways.

"These guys have kind of took the bull by the horns, and they don't take no for an answer," Rogers said. "They are the anomaly. They're what reentry is."


It was 1984 when Oliver was charged with robbery and started his journey through the criminal justice system.

He was 19 then, and after falling from the fifth story of the Hamilton County Jail while trying to escape the following year, his mother called him her "craziest child."

The fall's impact cracked his pelvis and broke his wrist, he said. He still can't straighten one of his fingers.

"I can remember when I woke up, I ain't had no function of my legs, and my hand - my mother was a nurse at Erlanger then, and she came in that room and she looked at me. I thought she was just gonna start asking - she said, 'Well, it's official now. You my craziest child. You definitely crazy.'"

"I go by [the jail] sometimes, and I just look up there and say, 'Wow,'" he said, looking toward the six-story building where he fell nearly four decades earlier.

"I have these days when I just - I just reminisce, and I go back and I look over my life, not staying stuck there, but to [look at] where my life was ... how God has been so good and had his hands on me the whole time. And all I had to do - my mother used to tell me when I came in her house, 'Son, ain't nothing gonna change 'til you humble yourself.'"

By the time he was released on parole in the early 2000s, he felt lost.

"I really lost my sense of reality on what was really going on out here, 'cause when I got out, they had cell phones and all that," he said. "They didn't have all that before I went in."

He had his family to keep him grounded, but he fell into drug addiction and had to go back to prison for a few more years.

"I went downhill for two to three years and devastated my family," he said. "I can just remember asking God, you know, like it was yesterday. Fell to my knees and said 'God if you just - if this all I'm gon' do, you know, you can just take me on now. Because I'm being a sorry father, a sorry son ... just sorry."

He was released again in 2004, but it wasn't until he changed his surroundings - the people he hung out with, the places he visited - that he started to recover. He's been clean for 13 years now, he said, and married his wife Latoya in 2008.

"I'm doing everything the right way - I don't do drugs no more, I don't do nothing but work, take care of my family, be a responsible Black man out here in society," he said.

Oliver served one more three-month stint in prison after his parole officer made a home visit in 2017 and found his wife's firearm - something she'd purchased for security after their home was burglarized twice, and Oliver was working night shifts at a local manufacturing plant.

The gun had been properly secured and was on her side of the bed, and the judge ultimately dismissed the charge. But the parole officer sent him back to prison for the last few months of his sentence.

"It was the hardest day I think I've ever encountered to have to go back up in there," he said, adding that his employer of 12 years told him he could use his vacation time to keep his job and pick up where he left off when he got out.

But that wasn't the case.

"When I got out, they acted like they didn't even know me, and it was devastating," he said.

So with his wife by his side, he started all over again.

She bought him a little over $100 worth of dollar store cleaning supplies and a pressure washer.

"I gave him what he needed to start his first building," Latoya said, "you know, like a couple mops, brooms and cleaning supplies ... that's kind of what he started with."

"I didn't have my work truck then, so I folded it up in my little Altima, and I just hit the ground runnin'," Oliver said.

That was the birth of Oliver's commercial pressure washing business, TNT Cleaning.

Today, the 57-year-old has contracts with 12 buildings, has eight employees and is looking to hire more soon.

"I mean, God is simply amazing," he said, adding that his wife has played a major role in his road to redemption.

photo Staff photo by Troy Stolt / Tony Oliver poses for a portrait inside of Orchard Park SDA church on Tuesday, Feb. 9, 2021, in Chattanooga, Tenn. Oliver, who has spent a total of 17 years incarcerated in various Tennessee prisons, attributes his multiple stints in jail to youthful mistakes, and later drug addiction. Now 14 years sober, Oliver owns and operates a successful cleaning company, TNT Cleaning.


Fast forward to 2007, and JaMichael Caldwell was in his senior year of college driving back to Tennessee from Atlanta when he was pulled over by police in Cartersville, Georgia.

"I was in school, you know, doing my thing - doing good. I was doing excellent," Caldwell said. "And then, just this one particular time I went to Atlanta ... I always take the trip, but just this one particular time I got caught - first time ever being in trouble. They gave me a 10-year sentence."

It was for trafficking cocaine, he said.

He was only incarcerated for five of the 10 years, but it still took some time for him to transition back into society when he was released in 2012.

"You just got to ride your wave and believe in who you are," he said.

Growing up, Caldwell lived with his grandmother full time since the third or fourth grade.

"I had a lot of people in my corner," he said of his childhood. But his mother struggled with drug addiction, and his father wasn't really in the picture.

"That was one of my main things that kind of hurt me over the years as I had to sit in prison. I seen what the drugs did to my mom - and just in the community, period - and here I am selling 'em," he said. "So that kind of - I mean, I beat myself up for that for years, you know. And I still think about it. Like, I can't believe I was doing that. And it hurt. It hurt 'cause I actually saw my mom [struggle]. It wasn't like folks was just telling me - I saw my mom."

Caldwell turned to selling drugs after his grandmother died in 2005.

"My grandma used to be like, 'I know you know better,'" he recalled thinking to himself. "But by that time she had passed. But I know for a fact if she wasn't deceased at the time, I would've been a different man because I respected my grandmama so much."

At the time, though, he was just 19 and a sophomore in college and found himself having to grow up quickly to be strong for his little brother.

"It was kind of heartbreaking," he said. "To tell you the truth, I still kind of deal with that daily. Ever since she passed, I really don't celebrate holidays. It's just a date. I don't cry about it - I might have my little spurts that I just think about it and I just have a breakdown or something like that. But normal days, I just think about it and it put a smile on my face."

When he got out of prison in 2012, it was mostly his friends and mentors who were his support system, he said.

He started looking for work and landed different jobs over the years, something he hopes others who find themselves in that position do as well.

"If you want it, you gotta go and get it," he said. "You can't just be like, 'Well, this job didn't work.' Well if that job didn't work, you got to go to another and go harder."

Caldwell, now 37, eventually started working as a welder at a local steel distributor and began saving money to open a cleaning business, Caldwell Cleaning Solutions, in July of last year.

"I started with a couple rags that we ordered off of Amazon, and we ordered some cleaning solution," he said.

Oliver and Rogers helped him get some additional supplies, too.

"I enjoy it," he said. "It was something I was doing in prison for free - I got my buffing and waxing certificate in prison ... so why not get paid to do it?"

"My life's been going good," he said. "I own my own business. It's excelling. It could do better, but you know, I can't complain. It pays the bills. It makes my wife happy and keeps my kids healthy."

"I want to put my family in a position to succeed in life," he added, "just like the American Dream."

Now, not even a year after he opened his business in the middle of the COVID-19 pandemic, he has contracts to clean six buildings for local businesses.

"There's always good people, and we all make mistakes," he said. "Everybody need at least a second chance – every good person."


Going back to 1995, just over a decade after Oliver first went to prison, Joe Jenkins sold drugs to an undercover officer and caught his first drug charge.

"I don't make excuses," Jenkins said. "I done what I done."

In the 26 years since then, he said, he's been a free man - "like, not in prison, not reporting to a probation officer, not having to urinate in a cup to pass drug screens" - for only one month. That was in 2002.

"I didn't say that to say, 'Oh, the system is this, that and the other.' We already know about the system. But I'm saying it to say once you start [in the criminal justice system], is true. That snowball, it just keeps on rolling until you make a conscious decision [to change]."

Jenkins made that decision when he was last arrested in 2013. He'd been out of prison and on probation for just over three years when he was caught up in a 32-man federal drug conspiracy round-up and was facing mandatory life in prison.

His first moment of clarity came when officers first put the handcuffs on him, he said.

"Me and God, we had a strange relationship," he said. "I had a point where I told God how I was going to do things. And that didn't quite work out in my favor. But when they arrested me ... I said to God, 'Man, what is going on?' And his words was, 'Do you still trust me?'"

"I'll never forget," Jenkins said. "I was walking in [jail], and I said, 'I get it now.' I said, 'From here on out, I go where you tell me to go, and I say what you tell me to say.'

Another moment came when he asked his attorney what she thought of him.

"'I'm highly disappointed in you,'" he recalled her telling him. "She said, 'Because, of all people, you could have done so much more for your community.'"

"Now, I could've took this another way," Jenkins said. "Here's a woman that I barely know. Here's a woman of another race telling me, you know - but I've never felt like it was a jab. I felt like she had wrapped her arms around me like she was an aunt ... And out of my mouth, when she said that, came to words, 'And I still can.'"

After that conversation, he said, "I had another level of inspiration - I had another level of purpose."

He eventually beat the charges, avoided the life sentence and only had to serve five years in federal prison.

While in prison, Jenkins got to work befriending principals, financiers, politicians, lawyers, and others convicted of white collar crimes.

He asked them to teach him how to write well, how to create business plans and proposals, how to manage money.

"My thing was that I had already gotten everything from the hood that they could give me as far as skills, meaning I learned how to survive in the streets, and I learned how to go to prison and survive in prison," he said. "At this point, none of those were my future plans, so I needed some different types of surroundings."

He said one principal edited a paper he'd written, "and when he sent it back to me, it'd have so many red marks on it!"

To this day, he's still keeps in touch with some of the people who helped him.

Now, Jenkins, 47, said he "won't be on paper [probation] much longer. I'm about to be free real soon." But "even being on paper, I have not allowed it to stop not one of my plans."

He's been working at a nearby electric utility manufacturer, climbing the ladder taking whatever new opportunity comes his way.

"For me to come home and accomplish everything that I've accomplished - I bought my first home this past summer," he said. "When I went, they said, 'You can have whatever house you want.' I was pre-approved, you know. And so, but I stayed grinding it out. On my job I don't just work 40 hours. I work what I can get."

On the side, he's started his own re-entry program - The BRAVE Effect - to help people trying to adjust to life after prison.

"So here I go from going to jail in handcuffs to going to jail to present my program," he said with a smile.

It's the "same hustle, just a different product," he added. "When I was in the streets, I don't recall taking days off."


All three men pointed to their faith, support system and their own change in mindset as factors that helped them move forward.

"Just stay motivated. Stay positive in anything you do," Caldwell said. "If you think about trouble, that's when trouble is gon' come to you. I don't think about trouble because I don't get in trouble. You can sense trouble before it comes. You just try to brush it off, like 'Oh, well it ain't gon' happen to me.' So my thing is, if you can sense it, don't do it."

When Oliver was growing up, he said, "All the men in the community really took their rightful place, which we got to get back to now ... They taught us morals, principles, values, to have character about ourselves, take pride in anything that we do. And the main thing that they did not tolerate then was disrespect. You always respected to your elders."

"Right now, I'm so active in my community to my other young brothers, just letting them know that, 'Hey man, there is a chance,'" he said.

The men often join Rogers in community outreach projects, such as helping feed and clothe thousands of people during the height of the COVID-19 pandemic last year.

Oliver, Caldwell and Jenkins all are thankful for Rogers' help, whether it was directing them to the right people to help get their businesses off the ground or providing them with inspiration.

"He give me positive vibes," Caldwell said. "Some days he might just send me a Bible scripture, and I just go back and read it. He send me songs that just motivate me."

That motivation, the inspiration, is what has driven all three men to change their mindsets.

"I had to relearn everything," Jenkins said. "I had to relearn what I like. I had to relearn learn what I would accept and what I wouldn't ... Trust me, I'm the one that don't have it all figured out still ... everybody have their own issues. But as far as this right here, I'm grateful and that's how I've done it."

As for Rogers, he said he's grateful and overjoyed to see men and women beat the system.

"When I see them win, I know we win because that keeps them out of incarceration," he said. "They are able to love their families ... They're able to build a foundation for their family, and they're breaking generational curses."

Contact Rosana Hughes at 423-757-6327, or follow her on Twitter @HughesRosana.

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