Jack Kennevan visited with prisoners at the Hamilton County Justice Center (Ohio) nearly every week for over a decade. After retiring from an inspiring career as a high school teacher, coach, and principal, he volunteered as a chaplain through Transforming Jail Ministries. Jack wrote 290 letters, one a week to men and women with whom he met and anyone who requested his letters. Prisoners then had something upon which to reflect back in their cell after talking with Jack at a simple table with two chairs. Conversations with Prisoners is a selection of about 40 of those letters. Jack's letters and conversations offer windows into jail/prison-life in the United States and the importance for us as citizens to imagine new possibilities for our world inspired by a love and deep respect Jack shares with all he encounters, all he calls brothers and sisters.