Now she can go about freely, doing what she loves most, like helping some of her old friends at the Richmond Justice Center. Several times a month, Winkler visits repeat offenders just to listen or talk bluntly about some of their problems, like drugs, alcohol and the wrong men.
"You going to be on your knees in the bathroom, doing some stuff you don't want to do, for one, for one more. Then, after a week they aren’t going to want you no more," Winkler told one inmate.
Winkler has known some of these women for years because she used to be in and out of jail with them.
"They be like, 'hey Vanessa, see you when you get back.' I be like, 'I know girl. I'll be back.' Who does that?" Winkler said.
What made Vanessa Winkler break bad?
From the age of 17, until she turned 36, Winkler amassed countless misdemeanors and 13 felonies for assault, drugs and prostitution.
Like many inmates at the Justice Center, it started early for Winkler. The trouble began when she was just seven.
"My uncles would come in my room, take me downstairs and do their thing. It was three of them," she said.
Winkler said she got tired of being molested and eventually used a gun to try to shoot one of her uncles. However, she ended up accidentally shooting her brother.
He survived, but Winkler said she still turned to drugs to cope.
Winkler is one of many former inmates who has developed close relationships with those currently behind bars and supporting them upon their release.
"Jail just does not work"
It's part of the jail's REAL Program. REAL stands for Recovering from Everyday Addictive Lifestyles. The goal of the program is to keep repeat offenders from coming back.
"It’s very well-known. Jail just does not work," REAL Program director Dr. Sarah Scarbrough said. "Simply locking someone up and throwing away the key doesn't work."
Dr. Scarbrough said they’re not just linking inmates with mentors, but also providing them with job training and using social media to keep those on the outside from ending up back in jail.
Scarbrough said Richmond’s new Justice Center is already much less crowded than the old jail.
In fact, an increasing number of non-violent inmates, like Jerome Bell, have been given the option to serve their time at faith-based recovery homes, with more mentors and structure.
"Back and forth to jail is not helping me or my kids, so, I’m trying to get my life back in order," Bell said.
Scarbrough admitted it’s tough to break the cycle. Most of the people in jail are at a fourth or fifth grade reading level and have trouble supporting themselves on the outside.
New mom back in jail
For example, we introduced you to Jessica Gentry a few months ago, when she was being released just in time to have her fourth child. She is now back in jail.
"I guess I have an infatuation with money and men and that's my problem, and drugs," Gentry said.
Winkler said she could relate to Gentry's problems and said sometimes the cure is lots of love from those who are on the right path. That is one reason why Winkler said she was driven to set a good example by constantly letting her former cell mates know, they too can turn their lives around.
Last month, in October, there was an average of 1,175 inmates behind bars at the Richmond Justice Center. That number is 200 fewer than the same period at the old Richmond City Jail last year.