Editor’s Note: This letter from Doug Cupery, director of church mobilization at Crossroads Prison Ministries, was sent to all Crossroads mentors earlier this month.

Dear Mentor,

Christmas brings back both warm memories and icy cold memories for me. It was during the Christmas season that I accepted Jesus into my life and experienced the warmth of His love in my heart. But Christmas also digs up cold, painful memories.

Christmastime in prison is incredibly difficult. Though prison is a noisy, crowded place, a dark cloud of loneliness would often creep into my heart. I remember wrestling with the shame of my past, wondering what could have been, longing for life to be different and missing my family deeply.

This is probably the experience of your students as well. Prison is a lonely place in general, but during the holidays, it’s almost unbearable. You may not hear about it in every letter. But, trust me, the loneliness is there.

During this Christmas season, it’s our job as mentors to point our students to the peace and joy that come from Jesus. There is no better time than now to remind your students about the joy that is available to them in Christ.

Think of the story of the birth of Jesus in Luke 2. What a sight it must have been when the angels appeared to the shepherds with the glory of the Lord shining around them, declaring: “Do not be afraid. I bring you good news that will cause great joy for all the people” (verse 10).

Remind your students that Jesus was born during a time of political unrest, oppression and injustice. Our Savior came to the world during a very dark moment in history. Encourage your students that Jesus is present with them in their darkest moments in prison, offering peace and hope.

I like to call the messages you write to prisoners “living letters.” They bring the hope and joy of Jesus to those behind prison walls. They shine light into the darkest of places. These letters you write are read over and over again by your students. When I was a Crossroads student, I read the letters from my mentors all the time. I still hold on to those letters to this day.

Not only do your students receive blessings from your fellowship, but the good news of great joy that you share with your students also comes back to you in surprising and unexpected ways. I often hear from mentors who feel so blessed and encouraged by the words that their students share with them.

As you prepare to write to your students during the Christmas season, here are a few things to think about:

  • Share a time when the Holy Spirit spoke to you and gave you peace and direction. “May the God of hope fill you with all joy and peace as you trust in him, so that you may overflow with hope by the power of the Holy Spirit.” (Romans 15:13)
  • Share a time when your heart was heavy—maybe you experienced discord in your family, you disappointed someone or you struggled with depression. “Why, my soul, are you downcast? Why so disturbed within me? Put your hope in God, for I will yet praise him, my Savior and my God.” (Psalm 42:11)
  • Write a prayer for your student, asking that they may have peace and comfort in their heart and a firm assurance of God’s grace and mercy through His Son. “And hope does not put us to shame, because God’s love has been poured out into our hearts through the Holy Spirit, who has been given to us.” (Romans 5:5)
  • Share what it means to you to be a mentor and what a gift it is to be able to write to your student in this holiday season. “One person gives freely, yet gains even more; another withholds unduly, but comes to poverty. A generous person will prosper; whoever refreshes others will be refreshed.” (Proverbs 11:24–25)

On behalf of the entire Crossroads staff, I wish you a Merry Christmas!

Doug Cupery Portrait

Douglas Cupery
Director of Church Mobilization