Raymond’s New Life (and My First Case)

By Barbara Berger Opotowsky

I was admitted to practice law in New York State in 1972. Despite working since then, it wasn’t until 2016 that I accepted my first client.

A casual post-retirement dinner with former colleagues elicited my indicating a need for “a little something more.” The quick response was: “You should take a clemency case.”

In 2015, Governor Cuomo had declared an interest in making clemency more accessible and called on lawyers to represent clemency clients pro bono. The New York City Bar Association was helping to administer a program to match pro bono attorneys with clemency cases and sent me an overview of Raymond Pittman’s history.

In 1979, when he was 24, Raymond was convicted of committing 2nd degree murder and three 1st degree robberies. He was sentenced to 45 years to life, with the earliest possible parole being January 2024.

When I was assigned the case in 2015, Raymond was 62. He was in Greenhaven Correctional Facility, a maximum security prison in Stormville, New York, where I met him.

In our first meeting, Raymond was initially cautious. Over the course of many visits, however, he became much more open and evidenced great remorse for what he had done, a keen intelligence, compassion and a wonderful sense of humor.

This person was not the one who entered prison, a corrections officer told me. “I have watched him become a leader and be able to take the initiative to try to help the younger men to become men.”

The Raymond who entered prison was someone who, as a child, suffered the kind of repeated trauma and neglect that we hear and read about so often. At six years old, he witnessed his mother’s death. Many challenges and losses, but few opportunities, followed.

The product of those years was the young man who committed the crimes in 1979. A  number of interventions laid the groundwork for his transformation. First, a program that provided training in nonviolent conflict resolution given by the Society of Friends, and then a 16-week course of study provided by the Sing Sing Muslim community designed to develop coping skills introduced Raymond to things he had never known. Conversion and a strong commitment to the Muslim religion further reinforced his transformation.

The months went by as I began putting the case together. First, the record had to be reviewed. We think of the world as being digitized, but decades-old court records beg to differ. What followed was many trips to White Plains to go through boxes, and then hours at a copy machine making copies of critical documents. And, with the passage of time, all documents were not available.

Fortunately, throughout this process, I had the assistance of the National Association of Criminal Defense Lawyers, which had initiated a program to counsel pro bono clemency lawyers. Raymond’s clemency petition was submitted to them for review prior to submission.

Knowledge of the record is important but is not the key to clemency. Key factors are remorse for the crime committed, conduct during prison and likelihood of a successful release without recidivism.

With regard to remorse, Raymond accepted full responsibility and had great remorse for the crimes he committed. In addition, he had an almost perfect disciplinary record with no infractions at all in over 15 years. And, he had been consistently employed since 1984.

But the system frequently did not meet Raymond’s hunger for growth. Education is the best example. In prison, Raymond received his GED and completed a year and a half of college classes before then-Governor Pataki cancelled all funding for college programs in prison. Centuries of debates question the role of prison, ranging from punishment to deterrence to rehabilitation. Whatever the purpose, few people spend the balance of their lives in prison, so not preparing them for life outside prison is clearly counter-productive.

The last piece of Raymond’s petition was how he would manage if released. Not surprisingly, after 40-plus years in prison, there were no relatives or friends surviving that could shelter and provide for him. Without an intervention, like many, Raymond would likely leave prison and need to live in a shelter. But Raymond had the incredible opportunity to have The Fortune Society agree to provide him housing and participation in their Academy upon release. The Fortune Society provides extraordinary reentry support to the previously incarcerated. If their program was significantly replicated, there would be far fewer formerly incarcerated people who are unhoused.

As it happened, Governor Cuomo did not grant Raymond clemency, nor did he live up to his commitment to significantly increase the number of incarcerated granted clemency. In fact, he granted fewer clemencies than many other governors.

Disappointment gave way to optimism when Governor Hochul took office and wrote to those who had petitioned for clemency under Governor Cuomo. She indicated that their cases remained open and under review. That letter further stated that with the applicant’s consent, the Governor’s office may seek input from the District Attorney in the county where the crimes took place. It was significant that the Westchester District Attorney in office in 2021 not only did not object to but affirmatively supported the clemency application.

But, once again, clemency was not granted, and the hope for a significantly increased number of grants of clemency was not forthcoming.

The time for clemency was over since you cannot petition for clemency if you have less than one year before you will be considered for parole. Raymond was scheduled for review by the Parole Board in September 2023. He was extremely fortunate to have the continued support of the Westchester District Attorney and The Fortune Society. In addition, the Parole Preparation Project provided invaluable expertise and support.

With a parole review, unlike clemency, Raymond had an opportunity to appear before the Parole Board. Three Parole Board members interview the candidate by Zoom for about 15-30 minutes. No counsel is permitted. It’s hard to imagine how someone who has primarily only interacted with people in the prison for over 40 years has to present before three strangers on a medium, Zoom, they had never seen. Raymond was surprised to see his face on the screen. One of the questions was what he would fear most if released. His answer, cell phones, was met by the Parole Board members’ laughter.

In New York, only one in three incarcerated individuals are granted parole on their first review. Raymond was one of them.

The reality began to sink in after Raymond was granted parole in September 2023 for release in four months. The Fortune Society provided a strong foundation. But how does someone with no apparent friends or family members to rely on begin to connect and function after being separated from society for 45 years?

The reality was surprising. I arrived at Fishkill Correctional Facility to pick up Raymond and bring him to his residence in Harlem. Upon reporting to the security guard, I was informed that someone was already there to pick him up. That someone was a fellow 15-year Honor Block resident at Greenhaven who had been released a few years before Raymond and didn’t want Raymond to be getting out without a friend.

Raymond jumped in the car and said, “I am petrified” followed shortly by “I have to get an education.”

After a joyous lunch, Raymond, his friend and I arrived at The Fortune Society, where two of the staff were also from Raymond’s Greenhaven days and one of his two roommates was a fellow Fishkill resident. In each of these encounters there was a connection and a warmth that was palpable. It became clear there was a community to support Raymond.

And if I had any remaining apprehension about how Raymond would adjust after 45 years of incarceration, they were fully dissipated shortly after he was released from prison. Six days after Raymond’s release, I received an email from a corrections-reform advocate: “I had the great good fortune … to meet Mr. Pittman yesterday in Albany, where he was with the Parole Justice Campaign – and clearly a very respected elder whom so many people were so happy to see.”

On day six, Raymond Pittman was advocating for change.

If you would like to assist with a parole application or represent incarcerated individuals in appeals from a parole denial or related litigation matters, complete the volunteer application for the Parole Preparation Project at

Barbara Berger Opotowsky is a retired lawyer who served as Executive Director of the New York City Bar Association from 1997-2013.