Pushkin. Hey, it's Jake Today. We're continuing with the Ronnie Karraschillo story. This is part two, so if you haven't listened to part one yet, you should definitely go back and do that now. So last episode we ended with Ronnie getting some good news or what seemed like it. Anyhow, the court basically told him, we think your sentence of two hundred to six hundred years may have violated a
clause in the Illinois Constitution. That clause, by the way, says quote, all penalties shall be determined both according to the seriousness of the offense and with the objective of restoring the offender to useful citizenship. Bottom line, Ronnie could now be resentenced. Well maybe. Last June there was yet another hearing to figure this all out. It took days.
Ronnie's lawyer, Michael Deutsch, brought in over a dozen witnesses to testify about who Ronnie was and is now, about the type of man that Ronnie has become in prison. One of those witnesses was Ali Prewett, a lawyer and Chicago activist. She talked about Ronnie and the people he'd mentored or inspired.
What really has stuck out to me over the years is the positive impact he's left on not only folks who have been incarcerated, but folks who haven't. He has this sort of positive influence and inspiring story and is just such a motivator for so many people, for his family, for his friends.
The State of Illinois had lawyers there arguing the other side, it's.
Always difficult in a post conviction proceeding to take what we know today and apply it to a trial proceeding that happened years.
And in this case, decades ago.
The circumstances of the crime, the facts of the unknw line crime, those have all been litigated, and as council said, we're not here to relitigate the facts of the case.
Basically, the state was saying, look, we're not here for a new trial. We're only here to determine if Ronnie Kerriskillo should be re sentenced. Now, Ronnie claimed that his sentence was unfair and disproportionate to his crime, but the state then argues, what really matters here is that Ronnie has a shot at release, and as long as he does well, then the sentence is fair.
And that is key to the decision and the key to the analysis here because mister Karraschio is eligible for parole.
In other words, perhaps six hundred years sounds like a long time, but he's eligible for parole. So what's the problem. And the judge basically agrees. What does this mean for Ronnie? Well, it means that he now has to place all of his hopes on getting parole. There's just one problem when it comes to the parole board. It's it seems that
he can't escape the notoriety of his own story. Ronnie's been in prison for nearly half a century, and he's stuck in a convoluted legal system, a system that perhaps could be gained by an operator like Bob Cooley, but which was terrifying to a guy like Ronnie who was trapped inside with no fixer to call. And I gotta tell you, at times, Ronnie's story felt a bit like
a Franz Kafka novel. There's a guy and he's stuck trying to find his way out of one darkened labyrinth after another, and every time it looks like there might be an exit, the lights flicker out. I'm Jake Halpern, and this is deep cover mob Land.
Thank you for using Securius you may start the conversation now.
This morning, Hey Ronnie, how are you?
WHOA Hey, we're all again.
Ronnie's been incarcerated since October of nineteen seventy six. Back then, Ronnie was a teenager and a gang member. One night he got involved in a fight. He says he shot off the gun to break things up and accidentally killed an off duty policeman, a man named Terence Loftus. Ronnie was sentenced to two hundred to six hundred years in prison, and afterwards he was sort of stunned. He says it took him years to realize what the sentence would really mean for him.
That's tak off and realize. Man.
He filed some early appeals that went well nowhere.
That's my father. Don't buy no more appeals, don't buy no more lawyers. I go to the parole book. I'm gonna see it and I shot this type of far away there's no attention in it, and I'll make parole.
Parole. That was Ronnie's big hope. Yeah. Sure, maybe he'd gotten slammed on his sentencing, but with good behavior, he hoped he'd get out on parole. So he gradually turned his life around in prison, he renounced his gang membership, He learned a number of trades, got his ged, found religion, became a mentor, he says, in so many ways, he became a different person. And he figured the parole board would see this, that they'd review the facts of his case and release him.
How many times have you been before a parole board?
I think thirty five times. At least thirty five times.
Over thirty times Ronnie's gone before the parole board. That's almost once a year. It's kind of like going to the Super Bowl annually and losing every single time. Ronnie just keeps getting told Nope, you're not getting out. Even so each year or so, when Ronnie comes up for parole, he keeps trying, keeps providing evidence of his rehabilitation, and talks about how far he's come.
My life has transformed so much from what I came as a youth. I was a poor student. I was not a bright educational book wise, not that I got my GZI started going to college. I have six seven different trades.
While behind bars, He's worked as an electrician, a welder, a locksmith, a pipe bender, and a washer dryer repair man. He's also trained to become a typist and a paralegal. He's mentored fellow inmates, giving them legal advice. He's coached the prisons baseball team and organized soccer tournaments for his jailmates. He's a pastor, and he's even written a Bible study workbook called Covenant with Abraham. Ronnie is not allowed to attend parole hearings in person, but his supporters are and
they do. They show up and vouch.
For him all different times, black, white, Latin, whatever, racist, different, ex gang members, different, and all of them write letters that I impacted their life. And I've been coaching them in Christianity for long and saying, oh, you live your life well, healthy, motherical, health, your family, and this is all I do for my whole forty six years.
Over the years, Ronnie has won over a number of supporters, including religious leaders, an Alderman, a US congressman, even one of the prosecutors who originally brought the case against him. That prosecutor, Thomas Breen, noted that Ronnie's years of menuring showed him to be a model for other inmates. Breen went so far as to compare Ronnie to the police officer he killed He said that Ronnie had quote many of the generous characteristics of a caring person, not unlike
Terry Loftus. Members of the media have also written about Ronnie's story, tracking his bid for freedom. All of this seems like it might tip the scales in Ronnie's favor, right, the only problem being the parole board itself. It's known in Illinois as the Prisoner Review Board. Now in theory, it's a neutral body that can reach its own independent verdict. Its members are appointed by the governor. Its ranks include
former parole officers, prosecutors, social workers, cops, and politicians. The board operates with virtually no oversight, and its decisions are not reviewable in court. Jorge Montes sat on that parole board for sixteen years.
I was a law and order and conservative Republican, and I was going to do what all conservative people should do, is keep them all in and not let anybody out. That's what I set out to do.
Jorge was a former prosecutor, and he was tough. He wasn't inclined to let many guys out. And then one day this one inmate comes up for parole. Jorge says, this inmate had a very strong case for being released, but Porge still voted no. He said he did it almost automatically, like that's just what he was supposed to do. And then something kind of odd happened.
The very conservative Republican chairman told me, mister Montez, is there something we're missing here? I said, well, why would that be. You're voting to deny parole for what appears to be a pretty perfect candidate for a parole. I said, in that case, I withdraw my emotion and I would move that we parole, I mean we did.
It was almost like on some level, Jorge was looking for permission to show leniency, to say, you know what, Yeah, this guy does deserve a second chance. Let him out.
And that started my journey on these issues. So increasingly I began to scrutinize cases, to really consider where there's somebody had changed their lives and that warranted a second look, a second chance. And increasingly I began to find that a lot of these people were really redeemable, and my votes started to reflect that.
All of that being said, when Jorge first heard Ronnie's case for parole, he says he wasn't persuaded, not at first anyhow, especially given the fact that Ronnie had killed a police officer. Jorge says that he voted against Ronnie a few times. At these hearings, the inmates are not
allowed to show up and speak for themselves. Instead, one member of the parole board speaks with the inmate and then presents their case, almost like a lawyer, but not really because the presenters they may have their own agenda and they might not advocate for that inmate at all. So maybe you're starting to get what I'm talking about when I say this whole process at times feels like something that Franz Kafka cooked up. Anyway, one day, Ronnie
is up for parole yet again. Jorge is still not convinced that Ronnie should be set free, and on this occasion, Ronnie's presenter is well, I'll just let Jorge explain.
There was a gentleman on the board named Dick Doria, and Dick Doria was a sheriff from Tupeach County. Formerly the sheriff a hard conserve, ultra conservative.
So bad news for Ronnie, right, But wait, because Dick Doria, the conservative former sheriff, when he made his presentation, he said something that really surprised.
Orge, and Dick said that it was impossible, in his professional opinion, that Ronnie would have killed this officer purposely intentionally. Impossible the kind of weapon he used, and Monster Doria I knew all about ballistics and weapons and calibers, and he made a wonderful presentation. He said, I'm not well. I'm voting to release this man because I think he did not intentionally kill the police officer.
According to Jorge, Dick Doria said that he looked at the evidence, the distances, the ballistics and the like, and determined it didn't add up. It didn't make sense that Ronnie had killed this cop intentionally, and this really got Jorge thinking critically about Ronnie's whole case, about Ronnie's intentions, his efforts to redeem himself, and even about the original sentence back in the nineteen seventies from Judge Wilson, and
whether it had been fair. In fact, Jorge says he came to feel that Ronnie's sentence of up to six hundred years did seem a bit fishy coming on the heels of the Harry at Lamand trial, and that this might be an instance of camouflage bias.
Well It makes sense to me that that a judge would behave this way and take it out on poor cas because he had just given this sniper who was well known in the community for being a mafioso. He gives them an out, he gives them, he gives them a past, and then of course he's got to cover his tracks by then, uh overreacting on the man. I thought that was an excellent arguments, and I believe.
That we'll be right back throughout this process. Ronnie has also faced another big challenge. The Chicago Police Department and the union representing its officers do not want him to get parole, so much so that they have physically showed up at his parole hearings. Jorge remembers this. He says, they made quite an impression.
The conference room was very tight, and Chicago would send busloads of police officers and they would all crowd in to the conference room that just fit the conference table, and there were all there are thirty cops standing around us, and they were looking over our shoulder and literally and as we're casting votes. It was very intimidating and very difficult.
I've seen a picture of this scene and I got to describe it to you. You can see the Parole board members sitting at a table, and then like a foot behind them is a whole crowd of uniformed officers literally hovering over them. With time, Jorge came to realize that Ronnie might not ever receive enough votes for parole. In fact, at one point he even wrote an affid
David on Ronnie's behalf. In that Affidavid, he said that despite Ronnie's quote excellent prison record and his strong family and community support, that he was repeatedly denied parole because quote, the victim was a Chicago police officer. Montez concluded that quote there are several members of the board then and now who will never vote for parole when the victim is a police officer. For Ronnie, none of this is encouraging.
You know, the constitution says, we have votes and we don't care how most you GOTU there. We don't care about none of it. You kill the police officers and they blaintly say, I'm not gonna vote for a police killers. So you know, how can I have them for mercy when they're telling me before the hearing's even done. So I mean, if I bring anybody in there to testify, I'll hope or anything like that. We don't want to hear that.
And this creates a real logistical challenge for Ronnie. Can he get the votes he needs to be released. Each time Ronnie is up for parole, the board is different. Old members cycle out, new members cycle in, and he's come close a few times. Each one of these moments is seered into his memory, moments when it seemed like maybe the door was about to swing open for him. In Justice Watch, a Chicago based nonprofit newsroom, has done
some excellent reporting on Ronnie's bid for parole. They found that in the years between two thousand and five and two thousand and eight, Ronnie had a series of parole hearings and each year he came within one vote of winning his freedom. Jorge can still remember these votes, how excitement would build as the board members cast their votes one at a time.
For those of us that were favorable to his release, it builds up a lot of momentum and expectation. And there's one, there's two, there's three. Oh, we're getting closed. I think this is it. He's gonna go home. And then we get to know. So that's it's very tense.
In two thousand and eight, Ronnie actually won a majority of votes from the board, six yeses and five no's. That's a win, right, Nope, The Illinois Prisoner Review Board requires that he get a majority of all members, not just those in attendance, and that day there were two no shows and only thirteen members on the board at the time, so his six vote majority it didn't count.
Jorge was the chairman of the parole Board at this point, and he says, to come this close and to fall short, it was really hard for him personally.
You feel deflated and you feel demoralized because if you really believe in this and you work his work and you try to keep work away from home, but if you believe that it's the right thing to do, and that we're keeping somebody locked up, a human being locked up, that in the you're you're sympathizing with the family and you see all the tears and you see people leaving devastated. Yeah, itated, it impacts you.
Ronnie wasn't there, but he soon got the news.
According to my law, I was supposed to be granted parole. I made the majority of the vote for me.
Like, what's that my going before the parole board thirty five times and getting rejected every time.
I never go in front of the whole committee. I see one person. One person comes and they call him my hearing officer. After that, talk to nobody but this one person. I'm up against an invisible body that I never see.
In twenty twenty, Ronnie was up for parole once again, and the event attracted attention from the local press.
WDN investigates comp killers going free.
Now another officer's murderer is appealing to the Illinois Prisoner Review Board for freedom.
This is a news report from WGN in Chicago that aired in September of twenty twenty, a few weeks before Ronnie was set to appear before the parole board.
You might think that killing a cop would lead to an automatic life sentence, but under old sentencing rules, inmates are fighting themselves eligible for release, and as we found, it often lands in the lapse of deceased officers' families to fight to keep them locked up.
The family members of the victim often come to these hearings. It's a tortured process. They talk about how hard it's been for them and how they hope that the killer will not be allowed to just walk away. In the WGN news story about Ronnie, a cousin spoke for the Loftis family. We are aging and we need to speak for him.
We need to speak for his parents and for his brother, and they are all gone.
I did read an interview with Loftus's brother before he passed away. He told the Chicago Sun Times that the shooting devastated the family, saying, quote, our mother was never the same. After that, the Fraternal Order of Police declined my requests for an interview, and the Chicago Police Department didn't respond to my requests for comment. But I did manage to find a web page commemorating Terence Loftus. A number of his friends and fellow police officers had posted
messages here. One read, I remember the night he was killed. He was showing me his new green leather jacket in the tactical office. A few hours later he was shot. I remember seeing him later at the hospital with a breathing tube in his mouth and the sounds of the air machine pumping in a steady rhythm. That vision to this day has haunted me and will until the day I die. Unlike the reprobate that killed him. Terry was
an honorable and exceptional person. Some of the posts were written directly to Terry, like letters sent to him in the beyond. One of those read quote, once again, parole has been denied for the individual that took your life and cause so much pain to those that love you. This time, the parole board said, he has to wait three years to be heard again. When that time comes, your brother, officers will be there again like they have been in the past, to stop this individual from getting
out of prison. You have not been forgotten. Reading these posts, it was heartbreaking, and I could see how, even all these years later, his friends and family would still be simmering with anguish and rage at the tragedy of it all. It also seemed almost cruel that year after year Loftus's friends and family members would be expected to attend these parole hearings and share these kinds of sentiments that they'd
have to relive their trauma again and again. I also have to wonder what Terence Loftus himself would say about all of this. I wonder how he would want to be remembered, what he would want his legacy to be, because after all. This was a man whose defining act was one of courage and decency. His biggest mistake, the thing that got him killed, was his inclination to help to step into the fray when he absolutely didn't have to.
For Ronnie, the whole situation is confounding. He accepts his responsibility for the death of Officer Loftus, he knows he's the one who pulled the trigger, and he says that he's done everything in his power to redeem himself. But as far as the justice system is concerned, there appears to be no real path forward.
I'm not supposed to mature and be able to have the constitutional right of being restored to useful citizenship. Judge didn't leave me no room for it. He just wasted me.
I'm wondering how in the face of being rejected for parole for thirty five times and being in is in for almost half a century, Like, how do you keep that faith in that hope lives well?
I studied who I was a day. I stay in the scripture that I pray every day. I pray with other people. Oh it's heartbreaking, especially when you lose family members down the line and they keep your faith so there's a scripture in there where it says what is Genesis fifty twenty, where what man means means for evil that God means for good? And in the Bible, God is is it just? God is just all justice.
This whole exchange oddly reminded me of something that Bob Cooley once said to me. He said that in his mind, the world of justice was divided into man's law and God's law, and then he put little faith in Man's law, I think because he saw it as arbitrary and fundamentally corrupt. But God's law, on the other hand, was pure and transcendent, and according to Bob, it's had a meaning for him.
And I kind of understood this. In a city like Chicago, where corruption and politics and gang violence and lingering class resentments all skewed the law of man, he almost had to grasp for something higher, hope that true justice might exist elsewhere, in some better realm. And it was here that Ronnie's faith resided. Though I wondered if he thought that this faith alone would actually get him past that parole board.
What do you think your chances of being released are.
I'm going to release I have faith in God, I pray every day. Did he put on the hearts of the just people, you know, to see the scenario, and they don't address the politics of it and give the judgment by law. I'm not gonna surrender myself all wanna die here, I'm not gonna. I'm not gonna go for it. I'm not. I'm not living that way.
If you were released tomorrow, what's the first thing you would do?
I was sit in the backyard basically looking up to see the sky. I see the stars at night, and the threat is over. So I came from a gang life. That threat never goes away. So the first thing I want to do is just go and just like, oh man, you know it's over, and then go live the life from there. I got so much time left to live. Basically, go be a help the humanity's supposed to do in the first place, be a giver. I was a taker as a kid. I can't take back my criminal activity
is akin. I can't take back, can't put the bullets back, and I can't do any of that. Not going to go forward.
This summer, Ronnie was moved to a new facility, a re entry center. Ronnie's attorney petitioned to have him move there. He's there to learn some basic life skills like how to write a resume and how to manage finances, skills that he would need if he ever makes parole. Ronnie is now sick four years old. He'll be up for parole again in November of twenty twenty two. This episode of deep Cover was produced by Amy Gaines and edited
by Karen Chakerji. Our managing producers Jacob Smith. Original music and our theme was composed by Luis Gara, mastering by Jake Gorski. Mia Label is our executive producer. Additional thanks to Jesse de Bartolomeo and Emily Horner, formerly of Injustice Watch and now at the Chicago Tribune for her reporting on Ronnie's case. I'm Jake Halpern. Deep Cover is a production of Pushkin Industries. For ad free listening and early access to upcoming seasons of deep Cover, consider becoming a
Pushkin Plus subscriber. You can find Pushkin Plus on the deep Cover show page on Apple Podcasts, or at pushkin dot Fm.