This book is designed to inform, enlighten, equip, and encourage servant-leaders and Christian workers who serve in the shadows of greatness in various forms of ministry to continue to serve with character, competence, commitment, and pride in the absence of accolades, appreciation, celebration, and recognition. The special ministries include Positive Youth Development for Boys and Young Men in At-Risk Situations, local church and faith-based organizations’ mission and outreach ministries, and especially a ministry in our nation’s jails and prisons. The motivation and inspiration for Part One of this book came through the author’s reflections of memorable life situations by several boys growing up on the south side of Chicago in the turbulent sixties and seventies who overcame tremendous odds for survival through their parallel faith journey and call to the ministry. It is designed to show how early foundation, formation, and understanding of character, civility, community, cooperation, coordination, competence, competition, and commitment can occur as young boys of color go from boys to men in the shadows of Berkeley Avenue in Chicago’s Kenwood-Oakland community. The motivation and inspiration for Part Two of this book are reflections of and learnings from evidence-based Christian Ministry in which the author has been engaged for nearly 50 years as a licentiate minister, 43 years as an ordained minister, 40 years as a Pastor and Teacher, and over 25 combined years as a Marion County, Indiana Commissioned Deputy Sheriff Jail Chaplain, Indiana and Louisiana State Prison Clinical Chaplain, Illinois State Director of Prison Fellowship Ministries, and 17 of those years as the Founder and former Executive Secretary (National Director) of the Prison Ministry and Criminal Justice Commission of the National Baptist Convention, USA, Inc., then representing 30,000 congregations, 61 State Conventions, and 7.5 million members.