Life on Parole

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NARRATOR: For a year-and-a-half, we followed four people in Connecticut as they left prison and were put on parole.

JESSICA PROCTOR: I’ve been incarcerated for a little over eight-and-a-half years. The judge gave me ten years. I thought it was the end of the world. And here I am. Ten days, I’m going to be walking out the door and starting my life over.

NARRATOR: The state is trying to use parole as part of an effort to reduce its prison population.

VAUGHN GRESHAM: When I get out, you know, hopefully, I get out of here and stay out of here. I’ve been here before, so it’s easier said than done.

NARRATOR: It is now giving parole to more of its prisoners than ever before.

PAROLE OFFICER: What are you going to do differently to stay out?

ROB SULLIVAN: Abide by all the rules. [laughs]

PAROLE OFFICER: Always good. All right? Good luck.

ROB SULLIVAN: Thank you.

PAROLE OFFICER: You’re welcome.

NARRATOR: The challenge is how to keep them from returning to prison.

ERROLL BRANTLEY: I’m proud to be graduating the prison drug program today because I did it with all you gentlemen. [applause]

I’ve been waiting for this day for the past 21 months. Next stop, outside. So pretty sure I’m going to see you there.

KATHERINE, Erroll’s Girlfriend: [sighs] I just want him home. I’ve been waiting for this for too long.

MARGARET, Erroll’s Mother: [waiting at prison gate] Open! Open!

KATHERINE: When Errol was coming home, I was more than excited. We were waiting for him to get out on parole and to come home. When you love somebody and you want to make a future with them, you kind of feel like all that is on hold.

NARRATOR: Erroll Brantley is being released from prison early after serving 20 months for drug possession and burglary.


MARGARET: Oh, my God, it’s been so long since I had a hug! I got a bunch of hugs from everybody!

KATHERINE: To just be able to put your arms around somebody is a huge thing.

ERROLL BRANTLEY: I got to go to parole,

MARGARET: Do we know where that is?

ERROL: 100 Sheldon Street, Hartford, Connecticut.

ERROLL BRANTLEY: I don’t even feel like I woke up in prison this morning, you know?

I’ve been coming to prison since 1999 now. And I’ve been in and out of jail 11 times. This time I got out was the first time that I was on parole.


ERROLL BRANTLEY: I was definitely frightened. I didn’t know what to expect.

MARK PAWLICH: Released from Carl Robinson, correct? Parole sentence of a little less than four years, right, 2019?

NARRATOR: Erroll’s parole officer is Mark Pawlich. He’s been a parole officer for 18 years.

MARK PAWLICH: So what was your crime over there?


MARK PAWLICH: Burglary? Is that kind of your thing or─

ERROLL BRANTLEY: No, not at all. I was─ for drugs─

MARK PAWLICH: All right. And your drug of choice is?


MARK PAWLICH: Mr. Brantley, you can just read, had a long, long history of opiate addiction. And if you’re in this business long enough, you know the chances are, at some point, it will rear its ugly head. So now he’s on your watch, so you got to make sure you’re dotting I’s and crossing T’s, that’s for sure.

So what we’re going to do today is I’m going to have you review these conditions now. So what I need you to do is read every one and make sure you understand each condition and then sign at the end.

NARRATOR: Among the conditions of his release, Erroll will have to undergo mandatory drug testing, and he’s barred from contact with prior victims, which includes his girlfriend, Katherine.

MARK PAWLICH: And is long-term planning being with your mom at that address? Are you going to kind of get on your feet, get a job, and─

ERROLL BRANTLEY: No, I want to go back home. I don’t live with my mom. I actually live with my girlfriend, Katherine.

MARK PAWLICH: That’s why I’m asking.

ERROLL BRANTLEY: But there was a problem at the jail. They said that she was a victim, and they took her off my visiting list after, like, 17 months.

MARK PAWLICH: Who’s the person?

ERROLL BRANTLEY: Katherine Eaton.

MARK PAWLICH: Was she a victim or not?

ERROLL BRANTLEY: No, she wasn’t.

MARK PAWLICH: What are they saying she was a victim of?


MARK PAWLICH: Did you ever burglarize your own house that she lived in or─

ERROLL BRANTLEY: No. Yeah, I took my TV to the pawn shop.

MARK PAWLICH: All right.

The Department of Corrections has a policy. When an offender is released, they can have no contact with previous crime victims or co-defendants. She called the police on him. She got him incarcerated and least got him sober, or cleaned up for a while. But she then created a─ the situation in the department’s eyes that she was a crime victim because he took her TV set.

There’s no staying overnight. There’s no nothing.


MARK PAWLICH: All right, following you out.

NARRATOR: Erroll leaves and goes straight home with Katherine, violating the terms of his parole on his very first day.

ERROLL BRANTLEY: I just wanted to stay close to the people that I love and feel protected. And I understand that parole, they have to do what they have to do, you know? But I was happy. I was home. That’s all I have up here. That’s all I need.

Yeah, welcome home. Absolutely. It’s a good place to be. I’ve been trying to get here for a long time.

NARRATOR: For the past several years, Connecticut has been giving offenders like Erroll more opportunities to earn early release, and there are now almost 5,000 people supervised by parole here.

But about a third of all parolees end up violating the terms of their release and are re-incarcerated.

MIKE LAWLOR, Undersecretary for Criminal Justice: If you’re on parole, you’re still sort of in the Department of Correction. You’re being monitored in the community by a parole officer, but in any day, for any type of violation, they can take you directly back into prison because you’re still technically serving your sentence, right?

NARRATOR: Mike Lawlor is one of the officials trying to turn this around and give parolees more chances once they’re out.

MIKE LAWLOR: It is not unusual for parolees to come back once or twice once they’re out, right? They didn’t commit a new crime, but they’re violating the rules of their supervision.

NARRATOR: One change has been the creation of a special unit devoted exclusively to the needs of women parolees. Officer Katherine Montoya helped start the unit.

KATHERINE MONTOYA, Parole Officer: Women are a different population. They have different needs. Their supervision needs to be different. My ladies oftentimes are the primary caretakers of their children. But then if they’re not doing good, if I remove them from the situation, who’s going to be taking care of those kids? So you know, it’s─ I do a lot of thinking after hours whether the decisions that I’m making are correct or not. So it’s hard.

So Jessica. I haven’t met her yet, but I’ve read her case. She came in when she was 18 years old. She’s going to be doing five years of parole with me. This is a pivotal time for her. She needs to make a decision right now whether this was just a one-time deal that happened in her life and she’s going to move on from this, or whether she’s going to be a returning customer, someone who keeps coming in and out of the system.

JESSICA PROCTOR: I did 10 years. I was young. I was 18 years old. I don’t think I should be on nobody else’s supervision. I’ve been getting watched for 10 years, OK, people stripping me, all that. I’ve been through it. Like, I don’t think that I need to be on nobody’s parole.

NARRATOR: Jessica Proctor went to prison for slashing another girl’s face with a razor blade.

JESSICA PROCTOR: I didn’t kill nobody, but you would have thought I did kill somebody, though. Ten years? Five years parole? I did think that was a bit excessive. So I─ I do hold some type of resentment.

NARRATOR: She got out of prison six days ago. This is her first meeting with Officer Montoya.

KATHERINE MONTOYA: So hi, Jessica. I’m Officer Montoya, your parole officer. How’s everything? So when you come here, you have a clear metal detector─

A lot of people think that being on parole is like you’re free. They’re not free, but there’s going to be a measure of freedom that is going to be afforded to you.

We’re going to be together for a while. It’s going to be five years. We might not see eye to eye every single time, but the point is that we have to work together. And the better you and I get along, the chances are your supervision is going to be successful. Let’s go pull a urine.

Jessica was young, got in trouble, went to jail for a substantial amount of time, came back out. She really wants to reconnect with her son. That’s one of her biggest goals in her life, to get her son back into her life, to be a mother to her son.

KANEISHA, Donte’s Godmother: So this is Donte’s bio mom, Jessica, my cousin. This is when she first went into prison.

NARRATOR: Jessica gave up custody of her son, Donte, and for now, they are not living together.

KANEISHA: I think for a long time, he thought that I was his bio mom, until my sister got pregnant. And he said, “I was in your stomach like that.” And I was, like, “No, papa, you weren’t in my stomach, you were in Mommy Jessica’s stomach.” And then from then on, I would just tell him, “You’re different than most kids because most people only have one mom and you have three moms.”

DONTE: When I was growing up, the only thing I really knew was, like, she’s locked up, and I’m like, “She’s locked up. So when is she coming out? When can I see her?”

KATHERINE MONTOYA: Reconnecting with family is so difficult, reunification with their kids. I always advocate for family counseling, for─ not only for the offender but as a family, everything together, because there’s a lot of hurt feelings. There’s a lot of anger. And people don’t have a lot of skills to be able to maintain a situation like that. So they’ll go back to their behaviors, you know, which is, like, drinking or drug use.

Substance abuse treatment house, Brooklyn, CT

RAEANN, Rob’s Daughter: [on the phone] Hi, Daddy!

ROB SULLIVAN: Hi, peanut. What did you do today?

RAEANN: My math quiz that I have. And I got 100 percent.

ROB SULLIVAN: Wow! Proud of you.

RAEANN: And picture day is tomorrow.

ROB SULLIVAN: Yeah, I know. You’re going to send me some pictures when they get developed.


NARRATOR: Rob Sullivan is beginning a month-long stay at this addiction treatment facility. For many parolees, Connecticut requires intensive drug and alcohol treatment as a condition of their release.

ROB SULLIVAN: Daddy’s discharge date’s moved to May 7th now. Daddy won’t be in the halfway house. He’ll be home, home.


ROB SULLIVAN: Well, I’ll call you at 8:00 and say good night.

RAEANN: OK. I love you.

ROB SULLIVAN: Love you, chewey.

RAEANN: Bye, Daddy.

ROB SULLIVAN: Bye, baby.

RAEANN: Daddy drew me this recently. And then he also drew me this one.

KELLY, Raeann’s Mother: He even put his teardrops [tattoos] in there [laughs], which he’s going to get taken off.

RAEANN: But that’s what makes Daddy Daddy.

KELLY: Yeah, no. Daddy’s Daddy without the stupid teardrops on his face.

RAEANN: So it still it makes Daddy Daddy.

KELLY: He’s more handsome with the teardrops off of his face.

She gets used to seeing─ you know, talking to him and then not. It’s just─ it’s been─ unfortunately, it’s been such a part of her life for her 10 years that’s she’s been here that it’s routine for her. But yet he sees how old she’s getting, and he’s tired of not being there and breaking her heart. So it’ll be, like, May 6th when he’ll be home.

RAEANN: It means Daddy’s going to be home sooner than we expected.

KELLY: And for what?

RAEANN: For my birthday.

KELLY: What a birthday present that’s going to be, huh?

RAEANN: He wasn’t there for my 10th, but my 11th is still important. So─ all my birthdays are important, so he’ll actually be here for my 11th. And that’s special to me.

ROB SULLIVAN: It’s hard, especially on a young kid, a young girl that’s you know, going into her teenage life, you know? A lot of children want both parents, you know? Right now, I’m trying to make it up to her and that’s by changing.

All this is stuff that I brang from jail, my criminal record. It’s a mess. I went in ‘92. I didn’t come back in until 1998, and then I didn’t get out until 2001. I came back in in 2002, got out in 2003, came back in 2005. The list goes on and on and on of how many times I’ve been in and out of jail.

With all these convictions and charges, it’s going to make it almost impossible for me to find a job, you know, and pay child support, which I haven’t done in years. I know I’m a scumbag in that aspect.

So $53,277, $25,156 and $25,935 for a total of over $100,000. Where the hell am I supposed get $100,000, win the lotto?

I have a real bad drug and alcohol problem, but it’s cheaper for me to buy a beer some nights for two bucks and get drunk and forget about all my problems, and that’s when I end up committing another crime. Sometimes I do it just go back to jail because it’s easier to live.

Watkinson House, Hartford, Connecticut

VAUGHN GRESHAM: I’m 25. The first time I was arrested, I want to say 16. First time I ever been to prison, though, went the full extent, was 18. I grew up seeing people getting robbed, stealing, selling drugs, shootings, stabbings, fights. When you grow up a certain type of way, it’s a way of life.

NARRATOR: Vaughn Gresham is doing seven years on parole, part of his sentence for an armed robbery.

VAUGHN GRESHAM: That wasn’t my first time, doing the robbery. It was quick, fast and easy. Nobody ever really got hurt. But if it got a little rough, we had bats, you know? Yeah, we had bats.

NARRATOR: He’s being released to a halfway house, where he must complete a 90-day program. The rules are strict and the residents are closely supervised.

TIFFANY BELL, Director, Watkinson House: Halfway house’s purpose is for guys to find employment, save money, and then return back to society, hopefully in a successful manner. Some make it and some don’t. But the reality of the situation is, if it’s not what they really want to do, they’re just not going to succeed, and they’re going to go back through the cycle.

NARRATOR: Since being put on parole a year ago, he’s been sent back to prison three times. This is his fourth halfway house.

VAUGHN GRESHAM: You know, I don’t want to go back. It sucks. It’s boring. I’m fed up with it. And my best chances of getting past this stage is keeping on the right path.

HALFWAY HOUSE STAFFER: So you got seven years parole, huh?

NARRATOR: Connecticut is now trying to give parolees like Vaughn more chances after relatively minor violations.

MIKE LAWLOR: Before, if you were a parole violator and you got returned to prison, typically, once you got back to prison, you’d be serving sort of an arbitrary time sentence, like a year. Now the amount of time you’re sent back to prison for is a relatively short period of time while we sort of reboot them and get them back out the door again.

Prof. FIONA DOHERTY, Yale Law School: The default mode in the criminal justice system, at least in the United States, is one of control and punishment. The big change in Connecticut is that the leadership is trying to make parole more about reintegration and less about punishment.

NARRATOR: Fiona Doherty runs a criminal justice clinic at Yale law school and has recommended additional changes to the way parole works in Connecticut

Prof. FIONA DOHERTY: The conditions that are put on people who are coming out of prison to avoid going back to prison are very broad. If we could all be sent to prison for being late, or occasionally having a glass of wine, or the other expectations and standards that are laid on parolees, we would all violate the conditions of parole.

NARRATOR: For Vaughn, those conditions will be enforced by his parole officer, Lisa Brayfield. She’s been on the job for a year, and her first assignment is supervising over a hundred men at two halfway houses in Hartford.

LISA BRAYFIELD: All right, Gresham?

Most of the offenders say, I don’t want to be here, I don’t know why I’m here, this isn’t right for me, I can’t be here. Maybe they see the structure and all the rules, and it may not be what they thought it was.

The main priority is going to be getting a job because you won’t be able to complete the program unless you’re working.

The rules and regulations that are given to parolees are straightforward and they’re all spelled out even before an offender is released from prison. Maybe it’s challenging for different people, but I don’t think it’s hard. If they want to make it work, they can.

You have any questions, concerns, issues, comments?


LISA BRAYFIELD: Nice meeting you.

VAUGHN GRESHAM: All right, have a good one.

LISA BRAYFIELD: And no drug use!



Prof. FIONA DOHERTY: The key to reforming the parole system in Connecticut is changing the dynamics of the invisible meetings that happen all over the state between parolees and their parole officers. If the atmosphere in those rooms is reflective of the reform vision of the top, then change in Connecticut will happen. And if it’s not, it will be very hard to make change stick.

NARRATOR: Today, Erroll has been called to an unscheduled meeting with Officer Pawlich.

ERROLL BRANTLEY: This is my parole office, 300 Sheldon St. I always get nervous every time I go through this door, man.

MARK PAWLICH: All right. So Brantley, why are we seeing each other today?

ERROLL BRANTLEY: I’m not sure.

MARK PAWLICH: Yeah, you are. I hold in my hand a lab report with your name on it. Is that starting to drag you into remembrance?

ERROLL BRANTLEY: No, it’s─ yeah, absolutely.

MARK PAWLICH: OK, so why didn’t you just tell us today that off the rip, then? How much did you use?


MARK PAWLICH: Just one time?


MARK PAWLICH: So you’re going to piss clean today?

ERROLL BRANTLEY: No, I’m not. No, I did it on Friday.

MARK PAWLICH: OK, so let’s slow down here because the 14th, which was a week ago, you were dirty for opiates. So you’ve been using consistently again?

ERROLL BRANTLEY: No, I haven’t. No, not yet.

MARK PAWLICH: So─ but you’ve used more than five total bags, though, in the eight days, correct?

ERROLL BRANTLEY: Yeah, six bags. Yeah. Not a bundle.

MARK PAWLICH: It’s hard. It’s a hard balance. I mean, you know, a lot goes into determining the levels of supervision. You know, years ago, my God, if you had a dirty urine, you’d go back to jail. Guys are not going back to jail even for a dirty heroin right now. I mean, they’re not going back the first time. It’s treatment, treatment, treatment.

If you don’t let me know what’s going on, then we’re just going to be chasing our tail again.

NARRATOR: Though he could send Erroll to jail, he decides instead to enroll him in a drug counseling program.

MARK PAWLICH: So to re-incarcerate instead of treatment on a dirty urine, it’s just not going to help that person move forward. And with Brantley, he’s probably been through rehab, you know, I don’t know how many times. And the unfortunate thing is, you just keep trying until one of them works.

REHAB EMPLOYEE: OK, so IOP is intensive outpatient treatment. Three days a week, all right?

ERROLL BRANTLEY: All right, thank you.

REHAB EMPLOYEE: You’re welcome.

ERROLL BRANTLEY: Appreciate it.

I do need more structure. You know, it’s just─ and I need the help. I need─ and they’re willing to offer it to me, which is amazing. So to have somebody on your side─ it went better than I planned.

NARRATOR: But Erroll doesn’t end up going to the outpatient treatment. He continues to use heroin and eventually checks himself into a detox center.

ERROL BRANTLEY: [on the phone] So here I am. I’m at ADRC. I’m waiting to get into the 30-day program. I wish I could have been the success story. I wish I could have shown you guys how amazing my life is, but it’s going to take a little while longer.

NARRATOR: He doesn’t tell Officer Pawlich and misses his next appointment, another violation of parole. It takes Pawlich almost a week to figure out where Erroll is.

MARK PAWLICH: All right so, here’s our update on Mr. Brantley. On the 31st, he was due in to report to me and he didn’t show up. Unbeknownst to us, the day he came in here, he had rendered a urine dirty for cocaine and opiates. So he left part of the story out. Phone’s going straight to voicemail. He’s using. He checked himself into a detox program.

I give the guy credit for going to detox and going into a program, but the way he handled it was completely wrong. And so basically, his violations are the dirty urine, not reporting to me that he’s no longer living at his residence. He’s really hanging by a thread right now.

Prof. FIONA DOHERTY: When we think about what we ask parole officers to do─ we ask them to be social workers who help reintegrate people into society. They’re also supposed to be the police officers. They’re supposed to be the people who catch parolees in any rule violation and then reporting it out. The question is, should the person who’s the parole officer be focused on helping somebody, or should they be focused on catching them for any rule violation?

Watkinson House, Hartford, Connecticut

HALFWAY HOUSE STAFFER: Gresham! Staff office.

NARRATOR: Vaughn has been at the halfway house for 10 weeks now. He’s going to a meeting with his parole officer with the hope of moving into an apartment.

VAUGHN GRESHAM: They informed me, like, Hey, all you need is an apartment and a job. And I got a job as soon as they told me that. And the apartment was already ready. She was just waiting on me to get out.

NARRATOR: Officer Brayfield has to approve his request.

CASE MANAGER: And we submitted his address, right?

LISA BRAYFIELD: Yeah. I mean, that’s not going to go through.

VAUGHN GRESHAM: I have another address.


VAUGHN GRESHAM: I have another address.

LISA BRAYFIELD: OK. Well, we’re not going to submit it yet.




LISA BRAYFIELD: Because I just wrote you a misconduct. You’re not in compliance with the program. You need to be in compliance with the program and working in order to be eligible to leave.

VAUGHN GRESHAM: And how long’s that going to take?

LISA BRAYFIELD: I don’t give a timeframe.

NARRATOR: Days earlier, Vaughn was late coming back from a job-training program.

LISA BRAYFIELD: OK. So what did you do when you left school?

VAUGHN GRESHAM: I went to the house.



LISA BRAYFIELD: OK. And were you authorized to do that?


LISA BRAYFIELD: So public safety is our number one priority because if they’re─ have a history of using drugs and going out and burglarizing people or being violent, we need to make sure that we don’t allow that to happen again.

So I have a misconduct for you. You are going to have limited community access for two weeks, and you’ll have to complete 10 hours of extra duty in the house. You seem really irritated right now.


LISA BRAYFIELD: All right. So you’re still working, right?


LISA BRAYFIELD: Any drug or alcohol use?


LISA BRAYFIELD: All right. So any other issues, questions, concerns?

VAUGHN GRESHAM: Lot of issues, no questions, a lot of concerns.

LISA BRAYFIELD: OK, do you want to elaborate?


LISA BRAYFIELD: OK, so two weeks starting today. I’m all set, if you are.

VAUGHN GRESHAM: [on the phone] Swear to [expletive] God, yo. [expletive] this [expletive] look like, man? The [expletive] what? Man I got a life to [expletive] live, too! I’m not about to stay in this [expletive] every [expletive] day all day, what? Go back to work, come back here. Man, what the [expletive] is that? That’s not even real life. [expletive] is going on man?

LISA BRAYFIELD: He was disrespectful. It seemed like he had a little bit of an anger problem when I was meeting with him─

All right, let me see your phone.

─which is initially the reason really why I took the phone.

Is there anything in here?


LISA BRAYFIELD: What do you mean “not really”?

VAUGHN GRESHAM: Nothing. Just texting.



LISA BRAYFIELD: OK, I’m going to look through this, I’ll give it to you in a little while.


LISA BRAYFIELD: I’ll give it to you in a little while. Do you have any other passwords on here?


LISA BRAYFIELD: I can’t see what you’re doing here.

VAUGHN GRESHAM: I’m taking it off right now.

LISA BRAYFIELD: All right. I’ll see you in a minute,

Phones are a big tool for us. It’s actually pretty common that the offenders will like to show off their drinking or their drug use, and they post these things to social media.

VAUGHN GRESHAM: All right, so you remember that night, when you and Cheese got the bottles for the first time? All right, so I deleted them [expletive] out of the phone. Them [expletive] been deleted. But I don’t know if she can bring them [expletive] back up because if she can bring them back up, [expletive] we’re going down. Make your phone calls, [expletive].

LISA BRAYFIELD: So once I took the phone, it was kind of the final straw, where I saw pictures of him drinking in the house. That’s an automatic remand because they’re creating a scene in the house. They’re making it a lot harder for the other offenders.

All right. Why are you so upset right now?

VAUGHN GRESHAM: I was told I was going to leave after I get a job. I got a job.

LISA BRAYFIELD: Yeah, if you were compliant with the program.

VAUGHN GRESHAM: Yeah. I didn’t think that was going to be a problem.

Prof. FIONA DOHERTY: You know, there are so many different ways one can violate a parole condition, if someone’s just looking hard enough, they’re going to find something.

PAROLE OFFICERS: [to Vaughn Gresham, putting on handcuffs] Widen your stance. Widen your stance.

Prof. FIONA DOHERTY: We know predictably from the evidence that the closer the oversight, the more violations you’re going to find.

MIKE LAWLOR, Undersecretary for Criminal Justice: There’s going to be failures because people are going to make mistakes. And for some people, it’s going to be impossible, right? No matter what you say or do, they’re not going to get their act together and they’re not going to stop committing crimes. Our number one goal is to reduce crime, not just to hold people accountable, but to─ you know, to do something to prevent crime. After all, you know, they call it the Department of Correction for a reason, right?

NARRATOR: Rob has now finished his treatment program. He’s living in a halfway house and gotten a job an hour’s walk away. But he’s frustrated because the money he earns is controlled by the halfway house.

ROB SULLIVAN: If I work 40 hours, I’m allowed to have $40. You get a dollar per hour of what you work to hold on you. I’ve got to go back and fill out a budget sheet and show them my check. They copy it. You know, so most of it goes into savings. But I can’t touch none of it.

Sometimes I feel it’s almost not worth it to work. Like, my daughter sent me a picture. She wants a pair of sneakers for basketball, and I can’t buy them. I told her I can’t buy them. I’m not allowed to touch my money.

Whenever Raeann has needed something, if I had the money, she always got it no matter what it was, you know? And it made me feel good. At that point in time, being on parole, they were dictating to me what I could do with my money that I earned. It was totally embarrassing.

NARRATOR: Rob also needs approval from the halfway house to go anywhere other than his job.

ROB SULLIVAN: Like, right now, even going in this store, I can end up back to jail, just for going into a store to get something. And I’m only getting a coffee.

You can’t do anything without permission. You would─ I would have to fill out a pass. If I got caught in the building, that’s a stipulation, it’s a violation of parole. I could have went back to jail for that.

You know, last week, I got to the point where I told the director, “You know what? I’m better off sometimes in jail. I don’t got to deal with all this [expletive].”

You know, when I was at the halfway house, I couldn’t see Raeann, at all, you know, my daughter. And it hurt. You know, it was hard. I went to work, and Kelly actually brang her to my job to see me, you know, for my birthday and to surprise me.

Hi, baby.

KELLY: Don’t cry!

ROB SULLIVAN: It’s, like, you have to be secretive. You have to be sneaky. You know, even though you don’t want to be, it’s like you have to be.

I love you.

NARRATOR: As the weeks go by, Rob is increasingly angry.

ROB SULLIVAN: You guys want to know how I feel sometimes? Well, right now, I’m pissed the [expletive] off. I got to please the halfway house so I can [expletive] go home. I had to go to 7-Eleven and get me a coffee even though I’m not supposed to because I really don’t give a [expletive] right now.

NARRATOR: After two months on parole, Rob has had enough. He flees his halfway house and is declared a fugitive.

ROB SULLIVAN: Friday, in the halfway house─ I went to work, and they told me they didn’t need me anymore. I got kind of fed up. And I wasn’t going to give them my last check and not be able to buy her Christmas gifts or nothing. So I said [expletive] it and I ran. So tonight, decided to come get her some sneakers and take her out to dinner because Thursday, I plan on turning myself in. And I told her, “Daddy messed up.”

You know when you do wrong, you’ve got to pay up, right? Right?


ROB SULLIVAN: You know it doesn’t mean I don’t love you!

RAEANN: I know.

ROB SULLIVAN: Come on, baby. All right, ready?


ROB SULLIVAN: And I won’t be around for Christmas again. All right, let’s find them.

RAEANN: I want the silver ones.

ROB SULLIVAN: Do you have them?

STORE CLERK: We got them.

ROB SULLIVAN: I kind of got fed up with the rules and having freedom dangled in front of me and then being told what I can do and what I can’t do. I actually went out and bought a couple bundles of dope, thinking I’d─ thinking I’d die. But it didn’t happen.

I love you.

RAEANN: I love you, too!

ROB SULLIVAN: Don’t cry! Come here. Why are you crying? You know you can tell me anything, right? Hey. You can always tell me anything.

RAEANN: I know! _[weeping]

ROB SULLIVAN: I will see you soon.

RAEANN: I know.

ROB SULLIVAN: No matter where I go─

RAEANN: I know.

ROB SULLIVAN: ─you can come see me.

RAEANN: I know.

ROB SULLIVAN: I love you.

RAEANN: I love you, too!

NARRATOR: A week later, Rob turned himself in. His parole was revoked.

KATHERINE MONTOYA: The business of living is very hard. And so when treatment ends and then it’s time for them to start to try to get a job, try to do what they need to do, we often see sometimes they get in trouble then because they just─ they don’t know anything else.

NARRATOR: Jessica has been taking classes to become a nursing assistant and working on her relationship with her son. But she’s just tested positive for marijuana and Officer Montoya could send her to jail.

KATHERINE MONTOYA: So you understand what you’ve done? Seriously, like, I’m here trying to save your ass. But I don’t know if you understand what you’ve done.

JESSICA PROCTOR: No, I know. I understood right after the situation happened. I don’t know, I think I was just stressed out and going through it.

KATHERINE MONTOYA: This could be a small [expletive] or it could be your descent into madness. And I need to understand if you’re just going to give this chance a try or you’re going to, like, keep [expletive] up.

JESSICA PROCTOR: No, I’m not going to keep [expletive] up.

KATHERINE MONTOYA: OK. I don’t want you to quit school, but if you find the school to be too stressful for you, if you need to take a break from school to kind of regroup, do that.

I am the one that holds the power to send her back. And I have to believe in her. I have to believe that she is going to do good because I make a living on second chances. That’s what parole is. They have to start over again. It’s hard for them. If I was to lock up every one that’s run into Jessica’s situation, I wouldn’t have a caseload.

JESSICA PROCTOR: I’m going through the same thing with my son.

KATHERINE MONTOYA: OK, with your son is a whole different animal.

JESSICA PROCTOR: My whole incarceration, he’s been a second honors student. And now he’s messing up.

KATHERINE MONTOYA: You have to understand, OK, you are the mother, but for the past 10 years, you have not been his mother. So for you to come into the picture and start calling the shots might be hard. Sorry, Jessica. Concentrate on the now. Concentrate on the future.

What is happening with her is pretty common of women that come out. They really put a lot of pressure on themselves, like pressure to try to make up for lost time. She’ll do good. I’m thinking she’s going to do good.

JESSICA PROCTOR: [at football game] Six to eighteen! Jesus!

Well, when I went to my son’s game, I was excited. I was emotional. I was there for the first time, and I should have been there his whole life. So that was what was bothering me.

Number 24, I can’t believe how big he is Oh, come on! What is y’all doing?

KATHERINE MONTOYA: I think that’s the driving force in Jessica. She really wants to be a good mother.

JESSICA PROCTOR: Hey, Don! Donte! Donte, you good?

KATHERINE MONTOYA: She wants to fix the mistakes of the past. And I feel bad because she went in so young and she was denied the opportunity to raise her son.

JESSICA PROCTOR: I love you. Call me later, OK?

He’s not happy. He’s not happy about this game. I have to give him his space because he’s just like me. So you know, when we’re angry, we don’t like to talk. We don’t like to be bothered. We just need to be left alone for a little while.

NARRATOR: Katherine has just picked up Erroll from the drug treatment center he’d checked himself into, and they’re heading to the parole office for the first time in over a month.

KATHERINE: Want me to come in with you?

ERROLL BRANTLEY: Yeah. I don’t know if you can come in, but we’ll try. Come on.

KATHERINE: We didn’t know what was going to happen because he just got out of a detox that was not sanctioned by his parole officer. And I’m there for support.

MARK PAWLICH: You’re here with him? All right, you’ve got to go out of the building. What’s your name, just so I─

KATHERINE: Katherine.

MARK PAWLICH: Katherine. What’s your last name?




MARK PAWLICH: Thank you.

MARK PAWLICH: Brantley, so I’m clear, is that the person you’re trying to get your residence with?


MARK PAWLICH: OK, understand that contact with previous victims─

ERROLL BRANTLEY: I have to take this off.

MARK PAWLICH: Don’t start this [expletive] again with me, all right?

ERROLL BRANTLEY: I have to take this off.

MARK PAWLICH: I don’t care about that thing right now. When I’m telling you something and you─ you know what? Go have a seat.

ERROLL BRANTLEY: No, I’m ready man. I’m sorry.

MARK PAWLICH: No, you’re not ready now! Don’t friggin’ tell me when you’re ready!

He’s given me every reason to lock him up, and I’m still working with him. He’s not taking any of his supervision seriously. He thinks it’s all, like, a joke and he gets to control and manipulate what he does and how he does it. So he’s going to get a rude awakening in about five minutes.

What happened out in the lobby raises my level of concern.


MARK PAWLICH: No contact with previous crime victims. Everybody from your first crime to your current crime is a previous crime victim. You can’t see, stay, email─ [crosstalk]

ERROLL BRANTLEY: The state─ the state has broken us up.

MARK PAWLICH: You can’t─

ERROLL BRANTLEY: She’s my support network, Officer Pawlich.

MARK PAWLICH: I got guys that can’t see their kids because the kids live with their crime victim. They sure as hell have never walked them up in my lobby. So today, you’re going to a halfway house. You’re due back in the house at a certain time every single night.

ERROLL BRANTLEY: I just don’t understand that it doesn’t bother you that I don’t have people in my life that I love. [crosstalk]

MARK PAWLICH: I’m going to warn you one more time. Don’t tell me how I think or how I feel. Understood? It’s got nothing to do with this. What I’m doing right now is managing somebody with about four or five misconducts right now that would land them in jail, and then to put the icing on the cake, walk their victim into my office lobby, all right─

ERROLL BRANTLEY: I really didn’t know it was─

MARK PAWLICH: ─And put it right out there in front of everybody, like, “I get to get supervised differently.” Well, you don’t get to get supervised differently.

ERROLL BRANTLEY: I didn’t know it was that serious. I’m sorry. I really didn’t know it was that serious. I thought it was something─

MARK PAWLICH: It’s extremely serious. Nothing you’ve done so far you’ve taken seriously. You’re also going on GPS today. If you charge it every day, like I’ve instructed you to for two hours, you’ll be fine. So you’re going to walk up and down the street. We’re trying to get a read on the GPS unit.

ERROLL BRANTLEY: [on the phone] He put me on the bracelet, and he’s putting me in a halfway house. And I can’t see you because you’re a victim. I’m sorry. This is not our fault.

MARK PAWLICH: I got, you know, 65 cases and one flaming [expletive] It’s just aggravating. She’s a crime victim. There’s no contact with previous crime victims. So some guys go straight to jail for that, right off the rip. Never mind all the other nonsense that he’s had.

ERROLL BRANTLEY: Why would you do this to somebody? I got one thing left in the [expletive] world that I’m close to, and the dude [expletive] won’t let me be there because he [expletive] he’s got something to prove. I seriously─ I wish he would just violate me. I just wanted to keep talking and go back to jail. So my life is pretty much ruined for the next [expletive] three years.

MIKE LAWLOR: In the past, parole officers felt that their main responsibility was to keep on top of the offender, and if and when they violate the rules of parole or commit new crimes, return them to prison. And that is changing. The goal is to figure out what we need to do to ensure that this person begins moving in the right direction.

ERROLL BRANTLEY: This is my new room. It’s very small. Home sweet home.

Cheyney House was my first time in a halfway house ever. I was crestfallen. Needless to say, I was very, very hurt when I saw the neighborhood that the halfway house was in because it was the neighborhood that I bought heroin in.

So this is the neighborhood they put a recovering heroin addict in. Here are some heroin baggies that litter the streets here. This is one of many heroin locations in this end of town. And it’s not that I’m tempted, but it would make it a lot easier for me to violate my parole and get this whole thing over with because right now, going back to jail and finishing my time seems a lot easier than the prospect of jumping through hoops for people that don’t want me to be happy.

MARK PAWLICH: Putting him in the halfway house he is going to always to see as punitive. I don’t care if he was happy or not, or thought it was punitive or not. It’s an opportunity, you know? Structure, supervision, money management, assistance for whatever, you know, they need is kind of all right there, having that structure and supervision right in his─ kind of in his face every day. So some guys respond to it. They’re never going to admit it, but some respond to it. So at least it’s not jail.

NARRATOR: Seven weeks into his stay, another parolee overdoses on heroin inside the halfway house.

ERROLL BRANTLEY: I just got home from work and parole was here, and this is what I come home to. Because of the overdose and death here today, parole came here and trashed my stuff.

LISA BRAYFIELD: So a few things to go over today. Do you have any questions before we get started?

NARRATOR: The day after Vaughn was sent back to jail, Officer Brayfield arrives to serve him his papers.

LISA BRAYFIELD: So I have your notice of parole violation, so we’ll go over it together. First part is going to be the charges that we have against you, so the condition that you violated is your release direction. On 9-7-16, your phone was searched, which produced a number of pictures of you consuming alcohol in the Watkinson House program. Based on your actions, you were in violation of your parole condition, and your continued supervision in the community is no longer compatible with welfare of society.

Unfortunately, Vaughn is not a unique case to me supervising offenders in halfway houses, you know, remanding him, bring─ he comes back out a halfway house, remand again, he comes back out to a halfway house. That’s kind of─


VAUGHN GRESHAM: I love the way you’re so nonchalant about it.

LISA BRAYFIELD: No. Like I said─


LISA BRAYFIELD: Like I said, if you did what you were supposed─ it’s─ this has nothing to do with me whatsoever.

VAUGHN GRESHAM: No, just your attitude, like, you know, it’s nothing for you to─

LISA BRAYFIELD: Absolutely. My hands are tied.

VAUGHN GRESHAM: ─send people to jail or anything, like, [expletive] them, you know?

LISA BRAYFIELD: Well, when guys are drinking in the house, right?

VAUGHN GRESHAM: People drink on the street.


VAUGHN GRESHAM: People smoke on the street.

LISA BRAYFIELD: OK, let me say this. I don’t care what other people are doing on the street.

VAUGHN GRESHAM: So you have family members that don’t smoke on the street?

LISA BRAYFIELD: I only care. It doesn’t matter. I only care─

VAUGHN GRESHAM: It don’t matter about your family members?

LISA BRAYFIELD: I only care about you.

VAUGHN GRESHAM: You don’t care about me.

LISA BRAYFIELD: The only─ I’m in charge of your supervision.

VAUGHN GRESHAM: Then say that, don’t say you care about me.

LISA BRAYFIELD: OK, so I’m only concerned about what you’re doing in a halfway house.


LISA BRAYFIELD: So when I see pictures of you drinking with other offenders in a halfway house, it’s blatantly clear that you’re drinking, I need to do something about it.


LISA BRAYFIELD: OK? Any other questions? Concerns? Comments?

VAUGHN GRESHAM: No concerns. No comments.

LISA BRAYFIELD: OK, this is your copy.

VAUGHN GRESHAM: So after this, I ever got to deal with you again?

LISA BRAYFIELD: I don’t know. It’s not up to me. You may be released to another halfway house. I’m not sure. OK?

VAUGHN GRESHAM: You know, I’m fairly easygoing. I do what’s asked of me. And one little─ you know, I drink. That doesn’t even cause any harm to anybody. But break─ basically brings hell upon on me, like, what─ I don’t understand that. I don’t understand it.

NARRATOR: After six months on parole, Jessica is close to finishing her nursing assistant program.

JESSICA PROCTOR: I wanted to go to school because I knew that if I came home, I didn’t have no job history. When I was younger, I wanted to be a doctor. So the best thing for me to do right now is to do CNA. I came home with a plan, and I actually stuck to it. I didn’t let little minor setbacks throw me all the way off. They docked [sp?] me off a little bit, and I got right back up and kept moving.

KATHERINE MONTOYA: Jessica walked to school or took the bus almost every day. It’s not like she had people giving her rides, or you know, backing for everything. Like, Jessica did everything on her own.

NURSING INSTRUCTOR: OK, guys, it’s the last night. I’m going to sit with you one at a time. I’m going to give you your grades and your packet that has your resume and your physicals and all that information.

Jess, I’ll take you. OK. Here we go. These are your test grades. Your test average was an 88 percent.


INSTRUCTOR: That is B-plus. Very nice. That’s your grade before clinical. Congratulations. That’s a super job. Your resume copies on resume paper.


INSTRUCTOR: All about being a nursing assistant. And your physicals. So you are ready to go get a job. OK? Any questions for me?


INSTRUCTOR: You are good. _[laughter] [unintelligible] That’s a good grade. OK?

KATHERINE MONTOYA: The whole point is for the offender to learn to do the right thing on their own. When they first come out, you’re like this. You have them. And as the offender starts doing good, and then you just let go. It’s hard work, but I think it can be accomplished.

NARRATOR: Erroll spent three months at the halfway house.

ERROLL BRANTLEY: I love this bass, dude.

NARRATOR: He stayed sober, found a new job, and got an apartment of his own.

ERROLL BRANTLEY: This became my place from my friend, Tammy. And she said she had a basement for rent. She only wanted 100 bucks a week, but she would do me a favor. She sponsored me and helped me to get out of Cheney House. But it’s got plenty of space, you know? Like I said, I have the biggest room in the entire house, which is nice. And it’s private. You know, I can come and go as I want through the back door.

I am headed to my first day of work at Ruby Tuesday’s as a manager-slash-kitchen- I’m not even sure. They want me to become a manager.

MARK PAWLICH: He’s got a skill set. He’s a smart guy, so there’s hope. You just could never say, “Wow, look at this case, this guy’s got no hope─ phew,” put him in your no hope pile. It would be very hard to do this job 40 hours a week, you know, month to month, year to year, decade to decade if you just really had, like, a no hope pile. I don’t have a no hope pile.

NARRATOR: Because of his turnaround, Erroll was finally given permission to have contact with Katherine, though they were still not allowed to live together.

KATHERINE: That was our first summer together. We decided we were definitely going to get married. Just more recently, decided that we’d like to have a family. So it’s all I look forward to.

NARRATOR: After nearly a year on parole, Jessica Proctor is graduating and spending more time with her son.

ANNOUNCER: Jessica Proctor.

DONTE: Some kids, they’ll never get to see their mom come out, do so well, finish school, and walk across the stage to get their diploma. I pretty much love her. I love her to death. I’ll do anything for her.

JESSICA PROCTOR: He was proud to see me come home and not go back, that I was actually making a difference in my life and going somewhere. So that meant a lot me.

NARRATOR: Rob Sullivan finished his prison sentence.

ROB SULLIVAN: Today I’m free. I didn’t have parole to look after me anymore. Only I look after myself. It’s like a sense of relief.

Here she comes!

Hey! Yeah, I love you, I missed you.

RAEANN: I love you and I missed you, too.

NARRATOR: He’s coming home just in time for his daughter’s 11th birthday.


ROB SULLIVAN: I don’t want to go that high.

NARRATOR: Vaughn Gresham is being released to his fifth halfway house after seven months in jail.

VAUGHN GRESHAM: Parole is a noose that you tighten yourself. You going to play? That noose is always going to be there. But as you go farther away from the path, it’s going to tighten up.

PAROLE OFFICER: These are your conditions, which you’ve signed a few times already.

VAUGHN GRESHAM: You stick to the path and you do what you got to do, you will be able to breathe. You’re not going to kill yourself.

NARRATOR: He has a new parole officer─

VAUGHN GRESHAM: These ones also?

PAROLE OFFICER: Yes. Come on, Gresham.

NARRATOR: ─and five years of parole still ahead of him.

A little over a year after Erroll and Katherine were given permission to be together, Erroll started using heroin again. They got into a fight about going to rehab, and she called the police.

ERROLL BRANTLEY: I feel ashamed for you to have to come and see me here because, you know, I was doing so well. It’s absolute and total regression. I don’t know if it’s apropos, if it’s bittersweet, if it’s going to help to tell the story. You know, I don’t know.

NARRATOR: He’s been charged with violating the conditions of his release, and now Connecticut must decide whether to keep Erroll behind bars or give him another chance at life on parole.

1h 54m
Lies, Politics and Democracy
Ahead of the 2022 midterms, a look at American political leaders and choices they've made that have undermined and threatened democracy in the U.S.
September 6, 2022