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Mentoring and being mentored: What I learned and taught at Sing Sing prison

Bill Webber was a bigger-than-life mentor and one of the kindest persons I’ve known. He was president of New York Theological Seminary, 1969-1983, and he was the prophetic voice behind the master’s degree in professional studies at Sing Sing prison. He was also among the visionary founders of the East Harlem Protestant Parish. When Rebecca Thompson and I reported for work at parish headquarters as summer interns in 1966, Webber informed us that drug addicts had ripped our assigned apartment to shreds. So he brought us to New York Theological Seminary, where we spent our first night before moving to a railroad flat near
the main East Harlem office.

Fifty-three years later, in the spring of 2019, Rebecca and I returned to New York Theological, now located at 475 Riverside Drive, where I had the privilege of keynoting the annual Urban Pastors Conference on the subject of mentoring. The day before my keynote address, two NYTS adjunct professors transported me to Ossining, New York, where I taught a three-and-a-half-hour seminar on mentoring with 40 master’s degree inmates at Sing Sing, the maximum-security correction facility. Both the pastors conference and the prison master’s class were using the book “Mentoring: Biblical, Theological, and Practical Perspectives,” which D. Cameron Murchison and I co-edited.

Evan, an older prisoner in the class, gratefully remembered Webber, praising his “theological expertise and vocabulary, which included subjects such as grace, forgiveness, justice, suffering, reconciliation and restoration.” (The names of all inmates have been changed for the purpose of confidentiality.) The two remarkable adjunct supervisors who had driven me to Sing Sing voluntarily led six to eight mentoring sessions there each month (pre-COVID-19). Both have full-time outside occupations, and both have served significant years of time as inmates there in what they described to me as the “Big House, up the river.”

Established in 1982, the Sing Sing master’s degree is surely one of the most unusual theological education programs in our nation. Each year up to 15 students who are currently incarcerated in New York State enroll in the NYTS accredited Master of Professional Studies degree offered inside Sing Sing. Candidates must apply through a regular NYTS application process. Those accepted are transferred to Sing Sing (if they are not already housed there), where they enroll in a one-year 36-credit graduate degree course of study. Candidates must demonstrate promise for leadership and an active faith commitment, hold an accredited undergraduate degree and meet all of the seminary’s other admission standards. Many elect to move from medium- or even minimum-security prisons to the maximum-security environment of Sing Sing in order to participate.

Master’s candidates attend classes five days a week. The curriculum provides foundational study in basic theological education disciplines: Old and New Testament, foundations of ministry, church history, theology, ethics, pastoral care, religious education, program design and administration. Courses are created to be relevant to the prison environment, with a strong emphasis on spiritual integration, community accountability and service to others. Master’s candidates work in field education within Sing Sing as peer counselors, chaplain’s assistants and tutors. Several also teach college-level courses online. They must maintain a 3.0 GPA to be in good standing and graduate.

Released graduates carry forward this transformative degree into society, working as ministers and religious leaders and in social services, national re-entry programs and other correctional systems. The recidivism rate for these graduates is close to zero for those who have been released over the past five years, compared to a
49% recidivism rate in New York State.

The life and language of prison

Now, please read the perspectives of the inmates, as they candidly initiated me with descriptive insights about their complicated and dangerous lives in incarceration.

In the safe space of our mentoring seminar, held on the stage of the Sing Sing auditorium, I was blessed to experience the kinder, gentler, gracious and more transcendent identities of the complex inmates. Everybody in the gathering expressed a desire to be a good citizen in the less safe territories outside the seminar.

However, those same men said that in the yard, mess hall, cellblocks and bath house, they must always be prepared to be vicious and physically able to take down a would-be attacker bearing a club or a sharp object or a lethal fist. As one prison researcher explains, “Unless an inmate can convincingly project an image that conveys the potential for violence, he is likely to be dominated and exploited throughout the duration of his sentence.” Most of the men, except the older ones, are physically buff. They spend hours in exercise spaces building up their bodies for self-protection and self-esteem.

I was bowled over by their personal testimonies that prison life is layered like an onion. They described the layers vividly, and told of how they must wear stoic, self-protective masks in many edgy or fearful contexts. They spoke of being beset by anger, hurt and depression. They witnessed to me that there is tremendous racism, bias and prejudice among inmates toward specific groups of prisoners. “We do our mentoring within a prison code,” inmate John explained to me. “We hate snitches. We hate gangbangers. We hate rapists, pedophiles and child molesters. Our code is also hostile toward those felt to be different, especially gay, trans or effeminate prisoners,” he confessed. At the time of my visit, John had served 20 years, with five months left.

Moreover, they shared with me that “prison language is coded and nuanced.” If a prisoner says, “I’m taking him under my wing,” the coded phrase is understood as “He is my sex slave.” I learned that “son-ing” is a unique prison code word for when an older, hardened inmate latches on to a naïve and weaker inmate, treating him as a trapped and controlled son who will wait on him as his personal servant. The seminar participants described “son-ing” as a primary example of unethical or bad mentoring — the antithesis of a healthy father-son relationship.

The men talked a lot about anxiety. I shared with them Reinhold Niebuhr’s teaching that anxiety can be both a precondition to creativity and moving forward and also a precondition to despair and destructiveness. Their honest and gut-wrenching wrestling with those possibilities was utterly profound. Perhaps the most brilliant student in the seminar had committed murder. His deepest anxiety came from a gnawing fear that his daughter would never be willing to have contact with him. Another inmate, Jacob, had served 14 years, with three more left. His anxiety-laden goal was simply “to survive in the moment.”

They taught me with these stark descriptions: “Prison is one of the most segregated places in the world; one of the most discriminating places in the world; one of the most degrading and humiliating places in the world.” They advocated the term “hyper-incarceration” over the term “mass incarceration.” A 60-square-foot shared cell takes up roughly the space of a king-size bed! Since the 1970s, the number of people confined to jails or prisons in the United States has increased 700%. Since the early 1990s, the U.S. has incarcerated more persons per capita than any other nation in the modern world. There are also increasing national numbers of so-called “supermax” or solitary confinement prisoners. That horrific practice is currently condemned as a form of torture by sociologists, psychiatrists, ethicists, theologians and other civic and religious leaders.

The Sing Sing seminar members also justly alleged that longer prison terms are predominantly adjudicated toward persons of color. The makeup of our 40-member class seemed to validate this contention: half were African American, three were Caucasian, the remainder were Latino. National incarceration rates for Black and non-Hispanic male adults are seven times that of white non-Hispanic males. Hispanic men are roughly three times more likely to do prison time as white men. Collectively, the 40 seminar men had served 350 years of imprisonment.

A freewheeling dialogue

Now, please examine with me a freewheeling dialogue among 40 prisoners and a wobbly 76-year-old with rheumatoid arthritis and a cane. Please ponder how I, the assigned teacher, came away so deeply taught and reformed by their winsome embodiment of the Spirit’s redemption, hopefulness and re-creative power.

The inmates and their two revered supervisors asked me to lead a dialogue about some major visions in the book “Mentoring: Biblical, Theological, and Practical Perspectives,” which they had been studying. I recall feeling that our rapport was like exciting tennis: the ball was bounced all over the court. Encouraged by their savvy supervisors, all class members accepted a chance to share. They resonated with my opening confession: “Throughout my life, I’ve always needed healthy peers and healthy mentors. Why? Because I can’t make it on my own.” Their moving feedback was vulnerable, for some even tearful.

They dug deeply into the notions that mentoring means “to abide,” “to remain” or “to stay,” as we unpacked the hymn “Abide with Me” and as we remembered how the risen Christ taught and nurtured two followers who did not recognize him on the road to Emmaus in Luke 24, and how he remained with them awhile in their home until they realized his saving personhood.

In a similar manner, they were touched by theologian Cristian De La Rosa’s practices of “accompaniment” and “facilitation” with Methodist teenagers and college students: walking with them and providing healthy contexts for them to meet and grow. “That’s what happens here, in this program,” the men declared.

They also resonated with preacher and theologian Thomas G. Long’s observation that mentoring often involves a kind of magic. As a grateful Eberhard Bethge once said of Dietrich Bonhoeffer’s creative leadership style at an underground seminary in Finkenwalde, Germany, he enabled students “to discover sources within ourselves that we had never previously imagined.” Yes, the magic of mentoring can give us our foundations and our wings. It can help us receive and pass on character from generation to generation. The prisoner participants defined character as “one’s inner essence, integrity, self-respect, trustworthiness and truthfulness to self and others.”

Long’s teaching that “all good mentorship” involves “a blending of closeness and distance” intrigued them. Thus, they readily aligned themselves with the following traits of intimacy and apartness in the ministry and teachings of the Apostle Paul (as unpacked by New Testament scholar David L. Bartlett in our book, “Mentoring”):

  • Interdependence/partnership/reciprocity;
  • Exhorting/correcting/reproving;
  • Setting an example/unforced influence/self-effacing style;
  • Sustaining and nurturing the relationship through hope in the mentor and mentee and hope in the unfolding influence of God.

Our seminar membership was made up of peers from three generations. They were clearly at home with peer and intergenerational mentoring that did not always involve a more senior or experienced person sustaining a younger. They were aware that while some mentoring can last for years, other mentoring could last only for a season or brief interlude. One post-prison program, called ARCHES, places former Sing Sing inmates (called “Credible Messengers”) with youths in the juvenile court system for 48 sessions, which last from six months to one year.


I asked the men to take a look with me through six windows. Our first window was Mentoring and Ethics. We grounded our dialogue in the following teaching by ethicist Rebekah Miles of Southern Methodist University: “We cannot do good mentoring without good ethics.”

“What are the traps, pitfalls and temptations whereby some mentors betray and undermine the ethics of character?” I queried. That led to our first group activity. We shared that some mentors are unethical by means of abuse, misconduct, manipulation, tyranny, promotion of adulation, immoral and criminal advice and transgressions related to power, boundaries, intimacy issues and confidentiality. The inmates, including some who had taken the lives of others, were intrigued by Walter Brueggemann’s sensational biblical example of bad mentoring: King David, on his deathbed, urging his son Solomon to murder all of his enemies. King Solomon acquiesced and followed his father’s horrific advice.

Some of the prisoners had suffered under heavy-handed influential pastors who had shamed them and bombarded them with hellfire-and-damnation sermons and teachings rather than lifting up the God of amazing grace who promises to lead us like a loving shepherd through life’s dangers, toils and snares.

We talked about a term used by my Southern California colleague Gabe Veas: “nuanced mentors,” who mix good mentoring with hazing, put-downs, arbitrariness and non-listening attitudes. Says Veas, they are complexly capable of “helping you the most and hurting you the most.”

As we shared in a group exercise about terrible times when we had been victimized by bad guidance, we found that some mentors had led men to violence, crime, incarceration, shame, anxiety and depression.

Our second window was Mentoring and Courage. One of the published prison study guides challenges inmate mentors to “have the courage and integrity to point out to mentees the actions that follow a criminal way of thinking.” Courage is no small matter in an environment that is constantly threatened by dangerous alternatives. It takes courage to seek a mentor and to be one in prison — courage simply to reach out to one another in a relationship that requires moral intimacy, vulnerability and demand. It takes courage for a potential mentee to dump his pride and to receive wisdom, help or even a demand to grow. As Jill Duffield’s foreword to the book “Mentoring” warns: “Mentors do not always tell us what we want to hear; they encourage us to grow and stretch.”

It takes courage to find the right blending of closeness and distance. It takes courage for a mentee to trust the one who sees in him the potential to become more than he currently is. It takes courageous vulnerability and risk for authentic change to happen. As Rodger Nishioka and Melva Lowry insist, in their challenging chapter on honest mentoring of youth, the mentor’s unconditional affirmation of the mentee is never enough. It must be accompanied by expectation and demand. That takes courage!

It takes courage to recommend another possible mentor when the relationship turns out to be the wrong foot in the wrong shoe. It takes courage for both parties to admit that it isn’t working. It also takes courage to end and celebrate a relationship that is complete.

I concluded this window with a question and a group exercise. “What courageous, expectant persons have demanded you to grow and stretch, either here or when you were free? Who are or were they? Name them aloud or in your heart. Thank God for them. Now, please take a minute and share that with your neighbor.”

Our third window was Mentoring and Imitation. Since loneliness is a major factor in prison life, I started this section by asking the master’s classmates if they experienced bouts of feeling alone. As all hands went up, I gave witness to one of my favorite biblical teachings. It is the promise that we will never have to walk through life alone. “The risen Spirit of Jesus Christ is everywhere, unbound by time and space,” I testified. “Jesus is with you always, as your abiding teacher, friend, anchor, leader and mentor. You will never have to be in any place, lonely or crowded, where he is not there also. His risen Spirit walks before you, behind you and beside you and breathes in you.”

I affirmed to my new friends that one of life’s greatest longings is to study and imitate our mentors. The Apostle Paul boldly put it this way to his followers in Corinth, Greece: “Be imitators of me, as I am of Christ.” I testified that Jesus calls us to imitate him as our primal mentor and friend. Thus, we cling to the time-honored phrase, “the imitation of Christ.” Yes, by the grace of God, we go through life imitating the examples of Christ and several others – those we admire and love – bending our lives to mimic theirs, both consciously and unconsciously. “Be a good role model,” says the prison study guide. “In some cases,” says the study, “the only role models prisoners have followed have been criminals. Offer the mentee an alternative example to follow, a person who is making it in the free world as a law-abiding citizen.”

Surely this is a primary way we grow into mentorship: by imitating and trying to be like our exemplars. As we grow, we find ourselves saying: “I’d like to be like So-and-so. I’d like to be like Grandma, or Coach So-and-so, or Nurse So-and-so, or Shopkeeper So-and-so, or Teacher So-and-so.” Undoubtedly, that was the mentoring magic behind Mahershala Ali’s dedication of his second Oscar to his precious grandmother at the Academy Awards.

Next, I asked the 40 inmates this question, which I’d also like to ask you: “Who are the ones you feel called to imitate? Who are the ones you yearn to grow and be like? Take a moment and name them to God in thanksgiving.” Then, we confided with a neighbor about a beloved exemplar we longed to imitate. Then, we shared with the larger group.

Our fourth window was Mentoring and Listening. Good mentors are good listeners. A wise seminary professor, William Oglesby, taught me more than 50 years ago that one of the best ways I can care for and abide with people is to get inside their skin or frame of reference and listen. Good mentors are servant listeners and trust-builders. We show up, and we consistently listen. As Mark Freedman jokes, mentoring is often about “showing up and shutting up.”

So I asked the inmates to wrestle with this question: “What does good listening create?” Please ponder our list:

  • Good listening helps create sanctuary and sacred space that foster hope and the possibility of change.
  • Good listening fosters the healing of our wounds and depression.
  • Good listening fosters personal sharing and communication that otherwise might not happen.
  • Good listening helps with our decision-making (such as thinking before acting).
  • Good listening fosters our ability to deal with problems, stress, anger, conflict, trauma, negative relationships and difficult emotions.

I told the master’s group about Nelle Morton, a profound mentor of mine who had received her master’s from New York Theological Seminary in 1931. She became a renowned civil rights leader and seminary professor. She was a death-defying freedom rider in the late 1940s, and she produced a prize-winning film about disabled children. Morton also made a monumental contribution, regarding the mentor as a compassionate, enabling listener, with this therapeutic phrase: “She heard me into speech.” Those empowering words have had a huge impact upon my life. For whenever I hear a mentee into speech, as a compassionate, enabling, servant listener, I actually affirm that person’s soul, integrity, worth and character.

Thus, I asked the Sing Sing mentoring class two questions:

  • Have you ever had the miraculous, transforming experience of being heard into speech, or enabled to spill your guts, by a nurturing servant listener?
  • Have you ever heard someone into speech?

We shared those encounters in small groups.

Our fifth window was Mentoring and Vocation. Throughout the spiritually developmental morning together, our dialogue was laced with the hopeful language of vocation. I started with this confession of faith: At the heart of mentoring is our biblical/theological understanding of self. The Bible promises us that God knows each human self by name, and loves each self as if there were only one self to love. The Bible promises us that God’s own breath or Spirit is in us: we are tinged by the Holy; we are touched by the Divine. And the Bible teaches us that we are made in God’s own image or likeness. Thus, my question to the seminar members: “Do you think of yourself as having God’s likeness within you, despite your scars and wounds?”

“This seems miraculous to me,” I confessed to the men, “especially as I study my own scars, wounds and baggage.” They responded with transparency and courage. To which I confessed that at the heart of our faith-based mentoring is the Bible’s promise that every human self is born with a purpose. We believe that God writes purpose in our hearts when creating us.

I confessed the Bible’s promise that God has a sacred calling for our personal talents and gifts. Together, we lined out this vocational poem by Edward Everett Hale, which I have shared for decades with students young and old:

I am only one but I am one.
I cannot do everything
But I can do something.
What I can do I ought to do.
And what I ought to do,
By the grace of God, I will do.

I also shared a few other vocational quotes that continue to guide my own steps on the journey:

  • Ida Eisenhower to her remarkable sons: “Boys, God deals the cards, but you have to play them.”
  • Boxer Joe Louis, looking back on his life: “I did the best I could with what I had.”
  • Katie Geneva Cannon to all her mentees: “What is the work your soul must have?”

Then, I asked the master’s students to bow in prayer and to talk with the Spirit about Cannon’s mentoring question for their lives, there in prison or someday outside in the free world: “What is the work your soul must have?” I mean, it’s a tough road ahead, and they know it better than most. I mean, it’s an almost impossible job finding a meaningful job when you’re incarcerated in a maximum-security correctional institution. Surely that’s a big reason why they’re studying mentoring. And I mean, it’s no easy job finding a job when you leave prison for the free world. But a piece of good and abiding news to cling to for dear life is this: They have their two incredible seminar supervisors to look up to and imitate for their road ahead. Both seminary adjunct teachers have done time at Sing Sing, and both now have meaningful work.

“I still have worth”

Inspiringly, the resilient men juxtaposed their bleak assessments of prison life with these compelling vocational affirmations and hopes:

  • Inmate Will had served 14 years, with two more left. He repeatedly testified: “My life in the Spirit has kept me sane.” He planned to help with a family business in the free world.
  • Inmate Kyle had served 49 years, with perhaps a little more than six left. A facilitator in the Protestant chapel, he engages in crisis intervention. “I’m in good health,” he rejoiced. “I love mentoring others to become more than they are. People haven’t given up on me. I still have worth.”
  • Inmate Chris had served 20 years, with only months left before entering the free world. “I had bad peers on the outside,” he confessed. “Many peers here on the inside are unsung heroes. Many of my peers are transformers who lead other prisoners toward change. Those peers gave me character.”
  • Inmate Shawn had served four years, with one left. “I have received a sense of confidence from this master’s program. I have just had a meal with two childhood friends who give me hope for the future,” he reported.
  • Inmate Antonio had served 23 years, with one and a half more left. “The master’s group has given me the ability to interact confidently with society,” he said.
  • Inmate Paul had served 17 years, with three more left. “I look forward to helping and being helped by mentoring as a ‘credible messenger’ in the juvenile court system,” he said. “Servant leadership is my calling. I have been greatly influenced by the writings of Howard Thurman and James H. Cone and by the doctrines of creation and providence.”
  • Inmate Diego had served 16 years, with six months left. “I will reunite with a supportive network of family and friends. I will try to find meaningful ways to give back,” he promised.
  • Inmate Mario had served 23 years, with two more left. “I am ready to be a different person in society,” he vowed. “I have learned to deal with prejudice.”
  • Inmate Hakim affirmed: “My goal is to live up to my potential. I have overcome self-doubt regarding academics. I have stuck to it with perseverance.”
  • Inmate Hernando had served 10 years, with a few months left. “I now possess a better sense of self,” he testified. “I also have a deep sense of mutuality and the determination to change.”
  • Inmate Andrew had served 40 years, with four more left. “My father has been my mentor through it all,” he said.
  • Inmate John winsomely thanked his master’s study peers and supervisors for “the gift of being seen as a person instead of a number. Thanks,” he said, “for mutual respect in community, for providing me sanctuary, responsibility, theological concentration, and a sense of humanity and purpose.”
  • Inmate Jamal had served 26 years. The day of our seminar he had but four days before release into the free world. (Let’s hear it for Jamal!) “Mentoring is now my responsibility,” he declared. “Mentoring is now my responsibility.” Jamal is remarkably buff, and I recall thinking that nobody would dare mess with him in the prison yard or elsewhere in the free world. Yet I remember even more his compassion and sensitivity regarding my arthritic mobility issues, as he tenderly helped me down 15 precarious steps to the restroom at the end of our seminar. May God bless, keep, and use you, Jamal.

I had to omit our sixth window, Mentoring from a Distance, because we ran out of time. That window expresses gratitude for the eerie miracle that people we’ve barely met, or even never met, can mentor us for decades. My adult life has been immersed in and shaped by the lives of Dietrich Bonhoeffer, Pearl Buck, Reinhold Niebuhr and Martin Luther King Jr. Yet I never met them. What persons have similarly shaped and shaken your lives from a distance?

The inmates did touch on venues of long-distance mentoring as they voiced special gratitude for the saving help of telephone conversations and the nurturing power involved in letter writing. “When you write something in a letter,” one prisoner affirmed, “you give it life.” Sarah Morrison is our neighbor at Monte Vista Grove Homes, a Presbyterian retirement village in Pasadena. She clearly understands this phenomenon of mentoring from a distance. For the past 10 years, she has corresponded faithfully with an inmate at the California Institution for Men in Chino.

Throughout my life journey, if just one solitary human being believed in me, I have found myself receiving the amazing grace to keep on keeping on and to try to make a way out of no way. So, at the end of our time together at Sing Sing, I gave each new friend this personal blessing: “I believe in you.” I called each by name and said, again and again, “I believe in you.” “I believe in you.”

“I hope you heard a voice today that you have not heard before,” said one of the prison master’s class supervisors as we debriefed at a Hudson River diner en route to New York City. All I could say was: “Spiritually, I will never be the same.”

Indeed, as they mentor me from a distance, those 40 men will infuse character and hope into my personhood as long as I live. And Hebrews 13:3 perfectly describes what will always be in my heart: “Remember those who are in prison, as though you are in prison with them.”

DEAN K. THOMPSON is president emeritus and professor of ministry emeritus at Louisville Presbyterian Theological Seminary. He and his wife, Rebecca, live at Monte Vista Grove Homes, a Presbyterian retirement village in Pasadena, California.