Smith still needed one last, crucial chance -- not from a parole officer, but from his family.
"Every time he got out, I was the one he called," said one of his younger sisters, Felecia Bryson. "It was like, here we go again."
All the same, Bryson put up around $3,000 in cash and signed a lease on an apartment for her brother. Now, she says, Smith is no longer using drugs and has achieved financial independence. He supervises clean-up crews for the city and carries a commercial driver license.
He tries not to think about his fellow inmates who are back in prison. "Going in and out of institutions, it can turn your heart a little cold at times," he said. "I've got to keep moving."
More than half of former inmates are imprisoned again within five years of their release, according to the most recent federal data. That figure is a challenge for policymakers such as Gov. Bruce Rauner, a Republican, who just pledged to reduce Illinois's prison population by a quarter over the next 10 years.
Rauner's efforts to reduce the prison population, along with those of other policymakers such as President Obama and Rep. Paul Ryan (R-Wis.), will rely on the families of inmates -- their connections, their resources, their capacity to forgive. Simply letting people out of prisons might not be enough, if they are returning to homes and neighborhoods where economic opportunity is scarce.
Research suggests that families, along with romantic partners and close friends, are an important part of the reason that former prisoners such as Smith succeed while others fail. The strength of these familial bonds, as measured by the number of visits prisoners receive behind bars, predicts how likely they are to commit new crimes after they're released. Prisoners who are married or in a committed romantic relationship tend to do better when they get out, as do prisoners with children.
Families provide more than emotional support. They help people returning from prison with money, access to credit, transportation, child care and more. They are indispensable, doing what no one else will do -- up to a point.
"Anybody who's been in and out of jail, especially those who have been using drugs or what have you, they've burned a lot of bridges," Bryson said.
Yet even where families want to help, they often confront the same obstacles as the prisoners themselves: a lack of education, limited income, poor credit, addiction, mental illness or criminal history, all of which make maintaining a job difficult. Smith was lucky that he not only had siblings who were willing to help him, but who had the means to do so.
The siblings' mother passed away when they were little, but as the oldest child, Smith took her loss especially hard, Bryson recalled. Their father raised them.
As an adolescent, Smith had a talent for basketball. He could have gone on to college as his sisters later would, but things didn't turn out that way, Bryson said.
"He had all the same opportunities the girls had," she said. "He made his own decisions."
After his last release from prison, Smith joined a program for returning inmates run by Chicago's Safer Foundation. The Urban Institute, which published a detailed evaluation of the program this month, conducted surveys on the relationships between the prisoners and the people who were closest to them after their release. That group included a few friends, preachers and cousins, but it was made up overwhelmingly of women -- girlfriends, sisters, wives and mothers.
Only 41 percent of this group was employed, and the average annual income among them -- including government assistance -- was under $10,000. Just 7 percent had a college degree.
And two-thirds said that they had welcomed a member of the family home from prison before.
For all that, only one in five described helping former prisoners as a financial hardship. On average, members of prisoners' families and their friends strongly agreed with statements that they wanted the prisoner to be a part of their lives and saw them as a source of emotional support.
Urban's Jocelyn Fontaine, on of the authors of the report, called it "selfless love" on the part of families.
"They've said to us, 'Well,' who else is going to do it?' and 'Of course I'm going to be there for him,' " she said. "I think that's why they don’t really see it as a hardship. They feel like that's what they need to do."
When Smith left prison, he was earning $125 a week in a work-release program for recently freed inmates. Without a bank account, he had no way of depositing paychecks. He could have had them cashed, but doing so would have incurred a fee.
Worse, Smith wouldn't have trusted himself with the cash anyway. He was a 40-year-old recovering heroin addict who knew he was going to grow old and die behind bars unless he did something about it, and he couldn't do it on his own.
He asked his sister to open a joint bank account and handle all of his checks. Every Friday after work, she'd drive to the distressed West Garfield neighborhood, where Smith was living in a halfway house, to get his check from him. She'd bring him a $20 bill, a box of Gatorade or whatever else he might need. Then she'd drive 40 minutes back to her three-bedroom house in the suburbs.
Once she realized that Smith was serious about changing his ways, she started to match the money he was saving in the account. When he was ready for his own place, she drove him around the city to look for apartments, and signed her own name to the lease because of her brother's bad credit. Nine months was the shortest term she could get.
The decision to sign the lease followed a consultation with their family about Smith's prospects. His siblings had "the financial security where we were able to carry him for as long as we needed to," said Bryson, an MRI technician at The University of Chicago's hospital.
"It's just fortunate for him," she said. "A lot of inmates, folks coming out, don't have the support like he's had."
"I wouldn't be where I am without them," Smith said.
Many families may not have been so welcoming. Many of the families of the returning inmates in the program refused to participate, and Fontaine and her colleagues were unable to reach them. Some might have wanted nothing to do with the former prisoner. Others might have been fearful of divulging information that could incriminate the prisoners or themselves. And some might have been too busy dealing with their own problems.
Sadly, having family around isn't always a good thing, noted Christine Lindquist of RTI International, a social- and health-sciences research organization headquartered south of Durham, N.C.
"Some family members may be a bad influence on the returning prisoner," said Lindquist, a sociologist, who was not involved in Urban's study.
"But at the same time," she asked, "what other options do they have?"