Medicine and medical research continue to grow rapidly in complexity alongside the changes in healthcare policy, discoveries, and the regulation and economics of the same. In the midst of these sea changes, patients and their families navigate (or negotiate) the reshaped landscape called the academic medical center or the teaching hospital. These changes create confusion and anxiety for patients and families in crises as the prospects of illness, death, and loss compete against and strain their coping abilities. A man they call Jacks helps patients and families navigate the maze. Jacks serves as a chaplain, and these are some of the stories he lives with the people God places in his care. As one who journeys alongside patients and their loved ones, Jacks embraces and struggles with the questions felt by so many but openly discussed by so few. He authentically strains to understand the circumstances in which people find themselves, without judgment, while controlling his own emotions to the things he witnesses. Jacks does not pretend to have the answers. Jacks understands one thing: compassion can bridge the divides created by crisis.