Restoring Families and Creating Meaningful Second Chances

What can a Christmas gift, a job opportunity, or a consistent mentor mean to someone affected by incarceration? For Jermaine Wilson, each became part of a journey toward restored relationships, renewed purpose, and community leadership.

In this episode of the Ministry Architects Podcast, Anthony Rogers and Mike Crain talk with Jermaine Wilson, mission ambassador with Prison Fellowship and two-time mayor of Leavenworth, Kansas. Jermaine shares how faith, Christian community, and practical support helped change his life, and how ministry leaders can support incarcerated people, their children, and those returning home.

Rethinking What Prison Ministry Includes

The conversation begins with the hosts’ experiences, including Anthony’s initial fear of entering a prison to lead worship and Mike’s involvement with Angel Tree Christmas gifts and summer camp.

Look beyond prison visits. Prison ministry also includes supporting children, building relationships with families, and helping people find stability after release.
Recognize how assumptions affect engagement. Anthony describes how worshiping and connecting with incarcerated people challenged his preconceived ideas about who they were.
Build relationships that continue. Mike shares how his church’s Angel Tree involvement extended into summer camp, where volunteers spent a week with children whose parents were incarcerated.

Ministry takeaway: Your next step could involve worship, children’s ministry, mentoring, family support, or reentry. The conversation identifies several ways to participate.

Understanding the Story Behind Incarceration

Jermaine describes growing up with poverty, his father’s addiction and incarceration, rejection at school, and a persistent desire for acceptance. Disruptive behavior brought attention, and he began seeking belonging through increasingly destructive choices.

Environment and personal responsibility both matter. Jermaine acknowledges his choices while explaining the circumstances and messages that shaped them.
Repeated labels can become part of someone’s identity. Hearing that he would follow his father’s path helped convince him that incarceration and addiction were his future.
Church attendance did not automatically become personal faith. Although his parents experienced significant change and the family attended church regularly, Jermaine says he knew God through their experience rather than his own.
Hopelessness affected his decisions after release. Believing that no one would hire or give him a chance discouraged him from pursuing employment.

For those supporting people returning home: Jermaine’s story highlights the importance of encouragement backed by real opportunities. A person who expects rejection needs more than a general assurance that life can improve.

Confronting Pain and Choosing a Different Future

The birth of Jermaine’s son gave him a sense of purpose, but it did not immediately change his patterns. After returning to drugs and being arrested, he received a three-year prison sentence when his son was eight months old.

Recognizing purpose and living from it were different steps. Jermaine describes losing sight of fatherhood as he returned to familiar habits and the search for validation.
Change required confronting earlier pain. While incarcerated, he recognized that he needed to address the brokenness that preceded his imprisonment.
His desire to interrupt a family pattern became a turning point. With multiple family members incarcerated, Jermaine wanted a different future for his son.
He began asking for help. His commitment to leave prison changed led him to seek a program that could help him grow.

Healthy Community Made Change Tangible

Through the Prison Fellowship Academy, Jermaine encountered men who welcomed him, prayed with him, shared food, and offered encouragement without expecting something in return.

He identifies six core values taught in the program:

Community
Affirmation
Productivity
Responsibility
Restoration
Integrity

These values helped reshape how he thought, spoke, and understood citizenship while still incarcerated.

When family visits, letters, and phone contact stopped, Jermaine began examining his motivation for change. He describes moving from trying to preserve his family through his own efforts toward a personal surrender to Christ.

After that encounter, he wrote down goals to become:

A faithful husband.
A great father.
A leader in his community.
Someone who would return to prisons to share the gospel.

Ministry takeaway: In Jermaine’s experience, discipleship included a welcoming community, practical generosity, values that shaped daily behavior, and a growing personal relationship with Christ.

Angel Tree Helped Reconnect a Father and Son

Through Prison Fellowship Angel Tree, Jermaine signed his son up to receive a Christmas gift delivered by a church on his behalf. He also included a personal message expressing his love.

After three months without family contact, Jermaine called home at Christmas. His son’s mother answered, told him the gift had arrived, and put their son on the phone.

The gift communicated a father’s love. His son received something from his dad despite their physical separation.
The personal message mattered. Jermaine could tell his son that he loved him, missed him, and was thinking about him.
The impact reached the caregiver. Jermaine says his son’s mother recognized his continued love for their family and later gave her life to Christ.
The experience restored hope in his role as a parent. Incarceration had limited what he could do, but the church helped him maintain a meaningful connection.

✅ DO: Clearly present an Angel Tree gift as coming on behalf of the incarcerated parent.

❌ DON’T: Let the church’s role overshadow the relationship the gift is meant to support.

Let Christmas Begin a Year of Connection

Jermaine encourages churches to see Angel Tree as an opportunity for ongoing ministry with families.

His suggested progression is practical:

Deliver the gift on the parent’s behalf.
Share the gospel and extend Christ’s love.
Pray with the family.
Invite them to worship with you.
Welcome and encourage them when they attend.
Invite them into Bible studies and continuing relationships.
Learn about their needs as those relationships develop.

Mike also challenges listeners to consider whether delivering a gift has become a substitute for sharing the faith that motivates their service.

✅ DO: Connect practical care with prayer, the gospel, and ongoing invitations.

❌ DON’T: Assume the relationship has reached its purpose when the Christmas delivery is complete.

Jermaine also encourages leaders to recognize the potential of those they serve. Families receiving support may eventually share their testimonies and become leaders themselves.

Make Reentry Support Concrete

When Jermaine left prison, a church welcomed his family and provided tangible support:

Employment.
Food.
A house that he says his family now owns.
Prayer and encouragement.
A pastor’s commitment to mentor him for a year.

That mentorship began with an invitation to meet the next day. Over time, Jermaine and his wife became youth ministers, and he also became involved in outreach leadership.

For ministry leaders: Jermaine’s account connects spiritual encouragement with practical stability. His church recognized his potential and invested in his growth through both support and relationship.

✅ DO: See the person’s gifts and capacity to contribute as you help meet immediate needs.

❌ DON’T: Reduce someone’s identity to their criminal record or assume they will always occupy the role of receiving help.

Serving Others Opened Doors to Community Leadership

Opportunities to serve in church encouraged Jermaine to serve throughout his community.

He returned as a mentor to the juvenile facility where he had been incarcerated.
He volunteered with Prison Fellowship in the prison where he had served his adult sentence.
He partnered with local police despite his initial hesitation.
Together, they organized a youth-versus-police basketball event and free food giveaway.

The event brought together people across racial and social differences, including people experiencing homelessness, church participants, and public officials.

Ministry takeaway: In Jermaine’s story, food, recreation, and partnership created an opportunity for people to meet and build trust. He remembers watching his son play basketball with law enforcement as a meaningful picture of unity.

Lead From Your Story and Gifts

After having his criminal record expunged, Jermaine considered running for public office. Fear and an unsuccessful attempt at traditional door-to-door campaigning nearly stopped him.

He eventually began connecting with people through barbecue, humor, and a brief account of how God had changed his life.

Make room for prayer and listening. Jermaine repeatedly describes pausing to seek God’s direction when he felt uncertain.
Do not interpret one rejection as proof that you are unqualified. He reframed rejection as a reason to seek the next opportunity.
Use the gifts and relational strengths you already have. Cooking and conversation helped him connect naturally.
Learn to share your story concisely. He communicated his testimony in roughly two minutes.
Recognize how your story can encourage others. People told him that hearing about his transformation gave them hope for themselves or an incarcerated loved one.

“If you can get people to laugh, you can get people to listen.”
– Jermaine Wilson

Jermaine went on to serve as mayor twice. He also describes collaborating with the same prosecutor involved in his case and expungement to provide free expungements for others in the community.

His desire to return to prison ministry eventually led to a full-time opportunity with Prison Fellowship.

Take a First Step Toward Prison Ministry

Jermaine closes by reminding listeners that Christian community and leadership already exist inside prisons. He encourages believers outside to connect with those inside as one body of Christ.

His starting points are straightforward:

Pray first. Seek direction about how to become involved.
Approach incarcerated people with openness. Examine the fear and assumptions that may be keeping you at a distance.
Connect with Prison Fellowship. Jermaine points listeners toward the organization for support in getting involved.
Explore Angel Tree participation. Support children whose parents are incarcerated and build relationships with their families.
Continue beyond Christmas. Walk alongside families throughout the year.
Support someone returning home. The episode highlights employment, food, housing, mentoring, and opportunities to serve.

At the time of the conversation, Jermaine reports that Angel Tree had served 270,000 children the previous year, with a goal of 290,000 for the year discussed.

For a ministry wondering where to begin, Anthony’s closing invitation is manageable: start with one conversation, one relationship, or one practical act of support.

Resource Mentioned

Prison Fellowship and Angel Tree: prisonfellowship.org
Jermaine directs listeners to the website to explore prison ministry involvement and opportunities to serve children with incarcerated parents.

Anthony Rogers – anthony.rogers@ministryarchitects.com
Mike Crain – mike.crain@ministryarchitects.com

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