Punish or rehabilitate? What prison looks like to people who know it

The Short Version

The people in these conversations who have been inside American prisons, or worked in them, do not describe places built to change anyone. A former governor calls the system merciless, a smuggler who served 33 years calls the prisons "awful awful evil places," and a comedian with an old felony says prison only warehoused him with smarter criminals [1][2][6]. Almost none of them argues against punishment itself. The former governor says most of the men he served with were guilty, and the comedian says the light penalties he got early on did nothing and that being arrested and processed is what deters [1][6]. What they object to is length without purpose, the absence of anything to learn inside, and a record that follows a person for life. The case for rehabilitation here rests on particular things that seem to work, such as a theater program and trades, and it comes with one hard counterexample: a man a lawyer helped free who was arrested for a killing about a month later [3][4].

Table of contents

What They Said

Rod Blagojevich: most were guilty, and the sentences were the injustice

Rod Blagojevich, the former governor of Illinois, served nearly eight years of a 14-year sentence for corruption before it was commuted. He maintains his own case was political [1]. What gives his account weight on the wider question is what he says about everyone else. "I mean, the overwhelming number the guys I was with, they did it. They were guilty. The prosecutors got it right," he says. What was wrong, in his view, was the sentencing: "the sentences are ridiculously unfair and wrong and they don't match up." [1] He blames one-size-fits-all guidelines that ignore a person's background, and the 1994 crime bill, and cites Alice Marie Johnson's life sentence for a first-time nonviolent drug offense [1].

He describes arrival in physical terms. "I went from a 50,000 square foot governors mansion to a six foot by eight foot prison cell," he says, with iron gates like the ones in films [1]. Because anyone sentenced to more than ten years cannot be held in a minimum-security camp, he spent almost three years in a higher-security prison alongside members of the Crips, the Bloods and a Mexican cartel [1]. Of roughly 950 men there, he says, about 300 to 400 were sex offenders, and around 2% were white-collar prisoners [1].

The social order was explained to him quickly. Officers told him that prisons run on racially segregated groups called cars, and that he should stay with the white one instead of walking the track with Black friends from Chicago. He agreed to sit with white inmates and refused to stop talking to others. About a year and a half in, he shared a table with a respected older Black prisoner who wanted, before going home after more than twenty years, to sit in the dining hall with a white man [1]. His long sentence gave him standing, because other inmates read it as proof he had not informed on anyone, and they pooled their commissary money to buy him toiletries and shower shoes [1].

He survived on routine and belief. He read the Bible every day for 2,896 days and says of prison, "I needed God." [1] He read Viktor Frankl three times and paraphrases him: "The last of the human freedoms is our freedom to choose our own attitude." [1] He ran ten miles on his first Christmas inside because physical pain dulled the other kind [1]. He notes that when a man is in prison for more than four years, the wife or partner leaves in more than 90% of cases, and that his own wife did not [1].

Work paid almost nothing. He earned $62 a year, and after his sentence was nearly commuted and then was not, he was put back in the kitchen washing pots for eight hours a day at $5.25 a month, where he was known as "the governor of the dish pit," [1]. What he wants to do now follows from that. He hopes to fund culinary and vocational training for people coming home who "have no opportunities to learn a skill that they don't teach in prison, but they should." [1] He says the system needs "mercy and redemption," and that he can bring a perspective on "how merciless our criminal justice system is" [1].

Roger Reaves: 33 years, and the difference a different prison made

Roger Reaves flew drugs for the Medellin cartel and spent 33 years behind bars in several countries [2]. He is clear about the bargain he made. Asked whether the money made him happy, he says, "No, absolutely not," and of the whole career: "It wasn't worth 33 years in prison." [2]

His judgment of American prisons is the harshest in these sources. He calls them "awful awful evil places," filled with hatred from guards and inmates alike and segregated by race, and says his final year, during the pandemic, brought the worst treatment of his life, including months in isolation and eight deaths in his unit [2]. He says prisons are full of people with mental illness, and that drugs should be treated as a health matter [2].

He offers a comparison from his own sentence. In Australia, after a first year under watch, he spent years in what was called a self-care unit, cooking for his housemates, and there he wrote about a million words [2]. He got through the rest by running daily, playing chess, reading two books a week and telling stories to other prisoners [2]. His advice to young people is to learn a trade early, and he says prisons should teach trades to inmates [2].

Tim Robbins: what a theater class does in a prison yard

The actor Tim Robbins started a program about 20 years ago, through his company The Actors' Gang, that now runs in 18 California prisons [3]. It does not stage plays. Participants use stock characters from an old Italian improvised form to express emotions in exercises [3].

His explanation of why this matters is a description of prison life. Anger, he says, is the one safe emotion inside, the "survival face" worn on the yard. Sadness, fear and even happiness leave a person exposed [3]. In an exercise, when someone approaches with anger, the facilitators encourage a different response, and participants learn that anger does not have to be answered with anger, in the scene or outside it [3]. They reach emotions that have been dormant for years and come to see themselves as "more than the worst act that got them there." [3]

The program deliberately puts rival gangs in the same room. Shared exercises, such as placing a flower on an imaginary grave, create bonds across gang and racial lines [3]. Robbins tells of two graduates, one Black and one white, who were ordered by their gang leaders to fight each other on the yard. They found each other and rolled around pretending to fight without doing any harm [3]. The group has also lobbied the state for more funding for arts in corrections, on the grounds that "art is a transformer." [3]

Josh Dubin: the second chance that went wrong

Josh Dubin is a civil rights attorney who works on wrongful convictions and resentencing. He had brought a man named Sheldon Johnson onto Joe Rogan's show after helping him get resentenced. Johnson had served about 30 years. About a month later he was arrested for allegedly killing and dismembering another man [4]. Dubin keeps saying allegedly, because he would be a hypocrite to call anyone guilty before trial, though he admits the surveillance footage does not look good [4].

He does not hide how it landed. "I called him a miracle on the show," he says, and the media threw that back at him [4]. His first thought was for the victim and his family: "This didn't happen to me." [4] His next was that this could tear down decades of reform work, and that he had let Rogan down [4]. The hate mail outweighed the encouragement [4].

Where he ended up is the most careful statement of the pro-rehabilitation position in these sources. "I can't apologize for giving someone a second chance," he says, but he can ask what he should do better [4]. He notes that a public defender organization and the Manhattan District Attorney also supported the resentencing and that nobody saw warning signs, and that recidivism among people released after very long sentences is under 1% [4]. He recalls an earlier case, a prisoner whose letters became a celebrated book and who killed a man just as it was being reviewed, as an example of how incarceration can damage people [4]. Rogan makes the same point about what the institution does: "There's a reality of taking a person who's convicted of a violent crime and putting him in jail with violent people for 30 years." [4]

Dubin's conclusion is about what happens after the gate opens. He had connected Johnson with a trauma therapist and held back from meddling. Now he thinks he should have been more involved, and he wants a stronger focus on reentry: mental health counseling, job training, making people feel safe [4]. A colleague who was once incarcerated told him why counseling is refused inside. It ran against the us-versus-them mentality, "And there was a stigma attached to it that I was soft if I did it." [4] The two planned a town hall in a tough New York prison to make asking for help normal [4].

He frames the choice for the country. "we incarcerate people at a higher rate than any other civilization on earth," he says, so society has to decide: "are we just going to throw people away and put them in cages and make them worse, even if they committed the crime," or try to rehabilitate them, since many are getting out regardless [4]. He adds, from his other cases, that "it's really easy to put someone in jail, real easy, real difficult to get them out." [4] And he says of the people he has helped who are doing well, "Not enough attention is given to the happy endings." [4]

Taylor Sheridan: a travel guide for the accidental inmate

The writer and director Taylor Sheridan tells of a man from his old gym, Tom Nelson, who had served 17 years after a life as a major drug dealer and armed robber, rebuilt himself through fitness, and ran a successful training gym until the pandemic closed it [5]. Around 60, broke, a single father of a five-year-old and fearing he had cancer, Nelson called for help. The mass turned out not to be cancer [5]. Sheridan would not lend money, joking, "I have a hundred percent failure rate of loaning money to friends," and proposed a book instead, modeled on travel guides: a guide to prison for someone who never expected to be there [5]. How Not to Die in Prison covers processing, the yard, food, commissary, gangs, disease, riots and jobs, and a publisher's offer after three chapters let Nelson support his daughter [5].

Sheridan and Rogan both call the system broken and designed to produce criminals, and Sheridan puts the recidivism rate at over 80 percent [5]. Nelson's story shows both sides: a man who did remake himself, and who was one business failure away from having nothing at 60.

Joey Diaz: punish early, then let people back in

The comedian Joey Diaz served time decades ago, and his view cuts against a simple reform story. Between 1983 and 1988, he says, he was arrested repeatedly for theft and possession and kept getting small penalties. "And what did that do? Nothing." [6] A ticket meant nothing to him. What registered was being taken in: "It's me going on to the station, getting processed, fingerprinted. That's what deters you." [6] He describes the sentence a judge finally gave him, zero to four years with reconsideration after a year, as the kind people should get: punish someone properly the first time, then see which direction they go [6]. He is frank that he walked out intending to keep using drugs and stealing, only more carefully, and equally sure he did not want to go back [6].

He has no illusions about what prison taught. "all you're doing is warehouse and me and put me back out," he says, and "You warehouse me with guys that are smarter than me and now gave me new ways to make money to steal." [6] There are not enough programs [6].

The lasting punishment, for him, is the record. Asked at a bar whether he was a Republican or a Democrat, he answered, "I'm a felon." [6] Decades on, he cannot volunteer at a recreation center or take a retirement job. "I could never do anything with that felony," he says, and "I found out the last three years how worthless I really was." [6] Rogan's response is that someone who has paid the price and commits no more crimes "should be a regular member of society," and that shutting people out sends many back to crime [6].

Rogan, Theo Von and Adrienne Iapalucci: the money and the numbers

The profit argument in these sources comes mostly from Rogan, in conversations with two comedians. With Theo Von, he describes private prisons and prison guard lobbies that have pushed to keep marijuana illegal to keep prisons full, and explains how, after slavery ended, arrests in the Jim Crow era forced many Black men back into unpaid labor [7]. He notes that California voters rejected a measure that would have banned involuntary servitude as punishment for a crime [7]. A search during the episode found that about 8% of state and federal prisoners, roughly 90,873 people, were in private prisons at the end of 2020 [7].

With Adrienne Iapalucci, the producer pulls up figures: about 1.8 million people in prison in the United States at the end of 2023, more than any other country, and a rate of 724 per 100,000, against 145 in England and Wales and 581 in Russia. Longer sentences are part of the reason [8]. Rogan asks what kind of person first thought profiting from prisons was a good idea, since it guarantees an incentive to lock more people up [8]. Iapalucci's contribution is smaller and telling. Talking about prison labor, she says, "if I was in prison, I'd want a job." Even on unemployment she got bored and needed a routine [8]. Rogan agrees that people need a purpose and an identity, and that work supplies both [8].

Where They Agree, and Where They Don't

They agree that prison as it is does not rehabilitate. Blagojevich says skills are not taught [1]. Reaves describes hatred and isolation [2]. Diaz says he was warehoused [6]. Sheridan and Rogan say the system produces criminals [5]. Dubin asks whether cages make people worse [4].

They agree that purposeful activity is what helps. Trades, in the view of Blagojevich and Reaves [1][2]. Theater, for Robbins [3]. Counseling and job training, for Dubin [4]. A job, for Iapalucci [8]. In their own cases it was reading, running and writing [1][2].

They agree that the sentence does not end at release. Diaz's felony, Nelson's precarious old age and Dubin's emphasis on reentry are the same point [4][5][6].

They disagree about how much punishment is needed. Blagojevich's complaint is over-sentencing [1]. Diaz's is the opposite at the front end: years of trivial consequences that taught him nothing [6]. In his conversation with Von, Rogan argues that crime rises when there are no repercussions, and criticizes prosecutors who release violent offenders [7]. These fit together better than they first appear. Diaz wants a real consequence early and a short one, with a review after a year, and Blagojevich objects to decades for first offenses. But a reader should see that the people here who favor second chances are not arguing for leniency at every stage.

They cite recidivism figures that point in opposite directions. Dubin says fewer than 1% of people released after very long sentences reoffend [4]. Sheridan gives an overall rate above 80 percent [5]. The two figures describe different groups, one a narrow set of older, long-serving prisoners and the other everyone, and neither speaker gives a source in these summaries.

The profit argument is strong on incentives and thinner on scale. Rogan's point is that anyone paid per prisoner has a reason to want more prisoners [7][8]. The figure found on his own show is that about 8% of prisoners were in private prisons [7]. So private prisons cannot by themselves explain 1.8 million people inside, though the lobbying he describes by guard unions concerns public prisons too [7][8].

They disagree, implicitly, about whether Johnson's case changes anything. Dubin's critics said it discredited the whole movement [4]. Dubin's reply is that one case does not outweigh the many who do not reoffend, and that it shows the need for support after release [4]. Nobody on the other side speaks for themselves in these sources; the criticism is reported by Dubin.

Why It Works

Why prison as described fails. People are housed with more experienced offenders and learn from them [6]. The only emotion that is safe to show is anger [3]. Life is organized by race and gang [1][2][3]. Seeking mental health help is read as weakness [4]. Work pays a few dollars a month and teaches no trade [1]. Long sentences end most marriages [1].

Why the things that help, help. Robbins's exercises give practice at responding to aggression without aggression, and put enemies in a shared task [3]. A trade or a book gives a person something to be on release other than a former prisoner; Nelson became a trainer and then an author, and Reaves and Blagojevich both left with books [1][2][5]. Work gives routine and identity [8]. Dubin's colleague visiting a prison to talk about counseling is an attempt to remove the stigma by example [4].

Why consequences still matter. Diaz's account is that penalties he could shrug off did not change his behavior, and that the experience of arrest did [6].

Why the record does harm. If a person who has served the sentence cannot work or volunteer, Rogan argues, crime becomes the available option again [6].

Where It Applies, and Where It Doesn't

The argument for shorter sentences is made here mainly about nonviolent and first-time offenders. That is Blagojevich's example and his stated concern [1].

The argument for programs applies to everyone who will be released. Dubin's point is that many are getting out whatever anyone thinks, so what they are like on release is a public matter [4].

It does not guarantee an outcome. Johnson had supporters, a therapist referral and a resentencing backed by prosecutors, and was arrested within weeks [4]. Diaz left prison still intending to steal [6]. Rehabilitation, on this evidence, improves odds.

It does not remove the need for policing or for consequences. Diaz and Rogan both say so [6][7].

These are personal accounts. Blagojevich's description of his own case is disputed by his conviction, and the statistics quoted in conversation come without sources. The value of the testimony is in what daily life inside is like and what followed, which is something these speakers know firsthand.

What To Do With It

1. Separate the questions. Whether someone should be punished, for how long, and what happens to them during and after are three different arguments. Blagojevich accepts the first for most prisoners and disputes the second [1].

2. Ask what a prison teaches. Trades and vocational training are the most repeated suggestion here, from a governor and a smuggler alike [1][2].

3. Support programs that give prisoners something other than anger to practice. Robbins's theater work is the example, and his group pressed the state to fund more of it [3].

4. Treat release as the start of the risk, not the end. Dubin's lesson is counseling, job training and closer involvement after the gate opens [4].

5. Make early consequences real and brief. Diaz's own suggestion is a meaningful first sentence with a review after a year [6].

6. Look at what a record blocks. Volunteering and ordinary jobs were closed to Diaz decades after his sentence [6]. Rogan's standard is that a person who has done the time and stays out of trouble should be an ordinary member of society [6].

7. Follow the incentives, and check the numbers. Ask who is paid when more people are locked up, and how large that share really is [7][8].

8. Notice the cases that go right. Dubin says the happy endings get too little attention [4]. Nelson and Reaves both came out and built something [2][5].

Sources

1. Rod Blagojevich · The Joe Rogan Experience
2. Roger Reaves on Smuggling for Pablo Escobar, Barry Seal and 33 Years in Prison · Lex Fridman Podcast
3. Tim Robbins on Saying No, Speaking Out, Prison Theater, Shawshank and the Magic of Being Alive · The Joe Rogan Experience
4. Josh Dubin on Second Chances After Sheldon Johnson, the Ohio 4 Case and a Weaponized Justice System (Joe Rogan #2228) · The Joe Rogan Experience
5. Taylor Sheridan on Ranch Life, Making Landman and Yellowstone, Broken Institutions and His Prison Survival Guide · The Joe Rogan Experience
6. Joey Diaz on His Memoir Tremendous, Quitting Xanax, Felony Life and Comedy Store Days · The Joe Rogan Experience
7. Theo Von and Joe Rogan on the 2024 Election, Trust, Community and Life After the Mothership · The Joe Rogan Experience
8. Adrienne Iapalucci on Joe Rogan: Dark Comedy, Gambling Families, Sugar and the Strange Side of History · The Joe Rogan Experience