After 24 Years in Prison, Mike Liebowitz Shines a Light on Connecticut’s Prison System

Mike Liebowitz (Courtesy of Mike Liebowitz)


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Mike Liebowitz, who was released last month after spending 24 years in prison, ran into a correction officer on his way out of Osborn Correctional Institute. The officer’s reaction? “Out for the holidays, back for the New Year,” according to Liebowitz.

“Which, of course, is a dig at the fact that most inmates come back to prison,” he said. “The irony was evidently lost on him that he is paid to help inmates not come back to prison, and that by saying such a thing is only a reflection on the poor job that he does.” 

Liebowitz, who was imprisoned in 1998 on a felony assault charge, co-authored the book Down the Rabbit Hole, a 2017 work criticizing the prison system and its failure to effectively rehabilitate offenders. Five years later, Liebowitz said, his thinking about the system hasn’t changed. If anything, he said, the pandemic has brought even more clearly into the light some of the things that he’s been arguing against for years. 

“They mandated, for instance, that we had to wear masks. The staff members simply refused to do it – not all of them, but enough of them,” he said. “When you are told to do something and told that it’s a rule, and then you see the people that are responsible for enforcing those rules not abide by it themselves — people just don’t respect hypocrisy, whether it be from parents, from teachers, law enforcement, or anybody else.” 

Liebowitz pointed out other violations he saw — prisoners who weren’t supposed to be sitting more than two at a table being told to sit together by corrections officers when the warden wasn’t present. 

Asked about his claims, the Department of Correction replied in a statement that they had instituted a number of protocols during the pandemic, including regular testing, temperature checks, quarantining and disinfecting, and that the positivity rate in the prisons was consistently lower than that of the general population.

In his book, Liebowitz argues that of the four main purposes that prisons were made for — incapacitation, punishment, deterrence and rehabilitation — they only succeed at the first one. He argued that part of the problem has to do with the lack of incentives for correction officers to rehabilitate prisoners.

“We know that they’re protected by a very strong union. We also know that their behavior takes place literally behind locked doors, out of public scrutiny. And then when you add to that mix, the fact that the only people that are ever likely to complain about them are criminals that people don’t believe and nobody really cares about — I mean, it’s a recipe for disaster,” said Liebowitz. 

In American private prisons, which profit from the number of people they house, Liebowitz said that the incentive is to keep prisoners within their walls.

Instead, he suggests that Department of Correction employees should be paid based on things like preventing escapes, recidivism rates and keeping the prisons secure. He referenced the private prison corporation Serco in the UK, which was given bonuses for a reduced number of offenders returning to prison. 

The presidents of the three branches of the state correction union said in a statement that they were “committed to ensuring the safety and security of all prisoners.” 

“Our unions not only advocated for DOC to hire additional correctional counselors to assist with inmate case management, but also made sure PPE was available during the initial stages of the pandemic to mitigate the spread of Covid-19. And we held the agency accountable to improve health and safety practices within the facilities as the pandemic raged. That’s what a strong and concerned union does—it strives to keep everyone as safe as possible in the most trying and dangerous circumstances,” the statement read. 

When it comes to reducing recidivism, Liebowitz also talks about the need for industry programs that would provide inmates with skills they could use in the workforce when they were released from prison. 

In his book, Liebowitz describes working in a wood shop where inmates did not actually learn skills that could be used in the world outside of prison. He writes that the supervisors of the wood shop and the upholstery shop didn’t have any knowledge of the trades themselves, and that they weren’t able to help the inmates learn how to perform the tasks correctly.

 “Ideally, if you’re going to work with offenders, you need to teach an abundance of skill sets. You need to teach them — yes, how to actually build things — but also how not to get upset when things don’t go your way. To have patience with the job that you’re doing to understand things are going to go wrong and you need to be adaptable, and you also have to understand when the inmates are trying to scam you,” he said. 

Liebowitz recounted a time when he was working in the wood shop, and inmates were using the wrong tool to build a certain type of chair. He said that even after he discovered that it wasn’t possible to do it using the machine they had, the other inmates continued to do it that way, damaging the final product. He said the supervisor seemed unconcerned. 

He writes that the lack of training often leads to jobs taking a much larger number of hours than they should without the inmates ever learning the skills they would need to be able to perform these tasks in the workforce. 

“The training is so non-existent and the standards of performance and productivity so poor in the industries woodshop that there are inmates who have worked there for years who still cannot perform some of the most common woodworking tasks,” he writes. “For instance, there are inmates who have not mastered basic sanding techniques, are unable to read a ruler, and can’t add or subtract fractions … moreover, they cannot properly plan the steps of a job, manage their time efficiently or tell the difference between common species of wood.” 

Asked about the claims, the Department of Correction replied in a statement that offenders who participated in the work programs, also known as “Correctional Enterprises of Connecticut,” or CEC, gained “valuable technical skills on various manufacturing machines and computer programs” as well as what they called the “soft skills” of “time management, teamwork, and problem solving.”

“It is important to note that the CEC program is a voluntary training program, and the majority of the participants initially have no work experience at all,” according to the the department.

Similarly, Liebowitz said, the rehabilitation programs that are offered to offenders in prison often don’t follow what he calls the “evidence,” – which he said demonstrates that offenders need to take responsibility for their actions. 

“The evidence, for instance, in regards to changing criminals is that they need to be made to feel guilty about their behavior. A lot of the programs tell inmates that they’re really good people and that they just made mistakes or it wasn’t their fault, it was society’s fault, whatever,” he said. “In my experience, that is more reflective of making the employees or the volunteers feel good and has nothing to do with what actually helps the change offenders.”

In some cases, he criticizes the programs themselves — he said that he believes that some programs, like Alcoholics Anonymous, are not created for criminal offenders. In the book he also criticizes the program Alternatives to Violence, which he said focuses on the frustrations that criminals have with society rather than the choices that offenders have made. 

 In other cases — such as a program called Good Intentions, Bad Decisions — he said the programs are good but they aren’t implemented correctly, and so they don’t achieve the desired results. 

Liebowitz argues that environment also matters when it comes to rehabilitating offenders, and can have a negative effect on programs that would otherwise function well. 

“The influences extant in the prison environment have the potential to undo the work of programming as quickly as it is done,” Liebowitz writes. 

The Department of Correction responded in a statement that they offer a variety of programs, many “evidenced-based and have been linked to a reduction of recidivism.” 

Recent data from the state that looks at recidivism rates over a three-year period found that 44 percent of people released in 2018 had returned to prison. That represents a drop from the 49 percent of those arrested in 2017 who were rearrested within three years. 

Liebowitz also criticizes the prison infrastructure itself, particularly at Osborn Correctional Institute in Somers, where he was held from June 2019 to November 2022. In 2021, Liebowitz wrote an article called “The Case for Closing Osborn Correctional Institute” where he writes that his entire block was relocated three times because of maintenance issues,  

“Osborn’s a dump,” said Liebowitz. “If you go into … C block, D block, E block, or F blocks — these are zoos. I mean, they’re, the bars are open, inmates are screaming out of them all day and night. I had a friend of mine that had a mouse in his bunk. It’s just — it’s disgusting and it’s just not conducive to helping inmates change.” 

The Department of Correction said the agency had full-time maintenance staff workers who were assigned to each prison building for “routine upkeep and emergency repairs.” 

Liebowitz questioned whether living in an environment where there are high levels of noise, cramped cells and upheavals from maintenance issues can impede prisoners from being rehabilitated. 

“How much personal growth, the avowed goal of modern penology, can be achieved while living in such an environment?” he writes. “Who could possibly want someone unimproved by such primitive conditions to move into their community upon release from prison?” 

Liebowitz told CT Examiner that he and his co-author Brent McCall focused on life inside the prison system because it was what they knew. But he also said there are things that can be done to prevent young people from entering the prison system at all. He referenced a program called Multisystemic Therapy, which he said has been shown to be very effective with juvenile offenders. The program involves therapists who work with young people and their families in an at-home setting on things like communication and problem-solving. 

But Liebowitz said he believes it also needs to come back to accountability. 

“I’m not saying that every time a kid steals a Snickers, you lock him up. I’m just saying that there has to be some deterrent in order to get the calculus in their lives to be that it’s better to change than not to change,”  he said.

Emilia Otte

Emilia Otte covers health and education for the Connecticut Examiner. In 2022 Otte was awarded "Rookie of the Year," by the New England Newspaper & Press Association.