Aaron Smith: From Hustler to Advocate for Second Chances

When Federal Agents Called with His Nickname

Aaron Smith was building two lives at once. While earning a business degree, he was also running a heroin operation on Chicago’s South Side that brought in $15,000 a day. The contradiction didn’t feel strange to him then, it was just Tuesday. Until February 6th, 2006, when his phone rang with a private number.

“They call me about my nickname, which was Ace,” Aaron told me about that DEA call. “You know, like private phone call, sound like a white guy. You know, like, I don’t know this person.” The agents told him they were at his mom’s house and wanted to talk. Aaron asked to speak with his mother, checking if they were “being respectful”, his code for asking if she’d cleared out anything incriminating he’d stashed there.

He told the agents he’d be there in 10 minutes. It was a lie. He never showed up. Five months later, federal agents picked up Aaron along with 47 other people in a single sweep. The 25-year-old college graduate with no criminal record was looking at 12 years in federal prison.

Growing Up Between Two Worlds

Aaron’s path started in a Chicago housing project, then moved to another drug and gang-heavy neighborhood. But his household was different. His mother emphasized education. His stepfather had been there since Aaron was one year old. Structure existed alongside the chaos of the streets.

“I’ve always been like this entrepreneur and vicious hustler thinking about getting money from a young age,” Aaron explained. Even at six or seven, he was ironing his siblings’ clothes for extra cash. The hustler mentality was born early, but so was the expectation of education.

He started dealing marijuana at 15, moved to crack cocaine around 17, then got involved with heroin through his older brother’s operation around 19. Aaron stayed in that world until his arrest at 25, all while pursuing his business degree. The two tracks ran parallel, he’d attend classes, then return to managing distribution networks.

In 2004 and 2005, Aaron tried legitimate business ventures. He started a t-shirt brand, wholesaled to stores, attended fashion shows. He even signed up for military reserves, looking for an escape route. But every attempt at going straight felt slow compared to the quick money of heroin sales. The streets kept pulling him back.

The Nightmare Lands

The federal investigation had been building for months. Aaron realized the scope when he saw a Chicago Sun-Times headline about overdose deaths linked to “drop dead heroin.” He knew his distribution network was connected to those deaths, even if he wasn’t selling hand-to-hand.

When the indictment finally came down, Aaron was ready for the worst. “I knew that I’ll be spending a long time in prison,” he said. “I was all in my mind. I already knew like once the feds come pick you up, that’s the law.” He just hoped to get home before turning 40.

The process from arrest to sentencing stretched almost three years. Aaron received 12 years, eventually serving nine years and five months after completing a drug treatment program. His mother was devastated. She’d just lost one son to murder nine months earlier, and now both her remaining older boys were facing federal time.

Switching the Hustle Behind Walls

Aaron self-surrendered to a federal prison in Minnesota in 2009. The intake process was jarring, a correctional officer asked who should receive his belongings “in the case of my demise.” Aaron had never considered dying in prison. Reality hit harder.

He spent almost two weeks in the hole waiting for bed space, not knowing if that 23-hour-a-day isolation would be his permanent reality. When he finally made it to the compound, he walked the yard with his head up despite having dreadlocks askew from two weeks in a cell.

“Everybody all eyes are on me. It’s 12 o’clock in the afternoon,” Aaron recalled. “And I’m just looking at them eye contact with everybody right like hey look ain’t no chump.” He was entering their world, their arena, and he knew they were checking him out.

Aaron found his foundation in three places: a brotherhood of men who were also determined to make it out, regular phone calls with his mother, and his Christian faith. He read voraciously, Victor Frankl’s “Man’s Search for Meaning,” stories of Nelson Mandela’s 27 years in prison, biblical accounts of endurance. If Mandela could survive nearly three decades, Aaron figured, he could handle his sentence.

More importantly, Aaron started teaching financial literacy classes inside. Fellow inmates noticed his approach to time differently. “People would ask me early on in my time, ‘You must be going home like this year because the way you’re programming,’” Aaron said. They saw someone moving like he was “short”, prison slang for having little time left. Aaron would tell them he still had eight or nine years remaining.

Building the Bridge Back

When Aaron’s release date approached in 2018, he felt the same surreal disconnect he’d experienced walking in. Nine years was long enough to become desensitized to time. He’d become the person newer inmates asked for advice on surviving their sentences. But leaving meant abandoning the brotherhood that had sustained him.

His brother, who’d been transferred to the same prison and become his cellmate for several years, was still there. Leaving felt like abandoning soldiers on a battlefield. Aaron and his closest friends had adopted a “no man left behind” mentality, they wouldn’t truly be free until everyone in their circle made it out.

But Aaron also knew he had work to do on the outside. All those financial literacy classes he’d taught in prison were preparation for something bigger. He’d spent years learning how to help people transition from the mindset that got them locked up to the mindset that would keep them free.

Second Chances in Action

Today, Aaron runs workshops in financial literacy and second chances, helping formerly incarcerated people navigate reentry. He operates a trucking company called U-turn that provides employment opportunities for people with criminal records. His “Escape the Odds” podcast features over 70 interviews with people overcoming their own nightmares.

The business degree he earned before his arrest finally has the legitimate outlet he’d always wanted. Aaron’s story has been featured on ABC, CBS, and other major outlets, not because he’s selling motivation, but because he’s creating concrete pathways for people coming home from prison.

His daughter, who was born while he was incarcerated, is now a teenager. Aaron missed her early years, but he’s building something she can be proud of. The hustle never left, it just found a different target. Instead of moving product on Chicago’s South Side, Aaron’s moving people from their worst mistakes toward their second chances.