1. On page 3, Mark asks the question, “How could someone so full of life be so read for death?” Sarge’s life was a constant balance between living in each moment and excitement for the afterlife. Do you think that he struck good balance between them? Why do you think that he wrote, while still young and healthy, the letter to his family for when he was gone? How do you think that Sarge’s experience in WWII, the early death of his own father, or the early death of so many members of the Kennedy family affected his perspective on death?

2. On page 40, Mark says that he believes that “the source of [Sarge’s] constancy was his radical faith.” How do you think that a radical faith can be the source of constancy?

3. On page 42, Mark says that Sarge was “not a politician,” and describes a lack of ambition for the kind of power that comes with political office. Sarge had many advantages over other potential candidates: he was politically astute, related a prominent political family, had an untarnished record as a public servant, and had a devoted personal following. Yet, he never won a political campaign.

4. Sarge’s work with the Peace Corps, civil rights, the War on Poverty, and the Special Olympics all have a theme of serving groups of people with societal disadvantages. Sarge was able to do this work without a “warped spirit of condescension” as Cardinal Stitch explains on page 68. Why do you think that Sarge is able to interact so easily with people of all intellect, advantage, and ability without condescension, even in casual encounters? How does his lack of condescension come through in other aspects of Sarge’s life or his disease?

5. Sarge had prominent friends at the highest levels of public and private life, and yet his best friend was his “Top Man” and “loyal lieutenant,” Richard Franklin Ragsdale or “Rags.” What do you think it was about each man that drew them together? What did each gain and give to the relationship?

6. When Mark founds the Choice Program, he is offered money from the Catholic Church to support his secular organization. When Mark presents his dilemma to his father, Sarge’s response is brief and to the point: “Hell, yes, take it…. Those kids don’t care what synagogue or church you go to – they only care that you are showing up every damn day. Take the check, deposit it, and then work with those kids.” Mark hesitates, but eventually accepts the money. Do you agree with Mark’s decision? Do you agree with Sarge’s reasoning?

7. Sarge lived his faith and applied it to nearly everything he did, something Mark describes on page 128 as “applied religion.” Later, Mark says that his father did not take half-measures with his faith, something he describes as “radical orthodoxy.” And yet, Sarge was able to change work within well-established and sometimes secular systems, such as the federal government and the Kennedy political machine, to effect change. How was Sarge able to apply a radical faith within these structures to effect change, without bucking the system itself ?

8. Mark often describes feeling rushed in his everyday life and wonders how his father was able to balance the demands of home and work life. Mark describes one reason for this lack of feeling “in the moment” on page 129 as, “the trappings of my generation” which he describes as “consumed by transitory things.” Do you agree with this assessment? Is the inability to live in the moment a symptom of life today, or are there trappings, albeit different trappings, that consume every generation

9. On page 133, Mark says that Sarge loved the position of catcher in baseball because “it put him in the middle of the action, calling pitches and moving fielders around to take advantage of the batter and the pitch count.” Catchers also work as leaders behind the scenes, getting little glory and even wearing a mask. What do you think it was about being a catcher that appealed to Sarge? How do you think that he “played catcher” in other aspects of his personal and professional life?

10. Although Mark associates himself very much with the Kennedy name, the focus of this book is not about his relationship with his mother, Eunice Kennedy Shriver. What role do you think that his mother played in his life? Was she an iconic inspiration, like the other Kennedy’s, or was she a living teacher, like Sarge?

11. Although popular discussion of the Shriver family is often dominated by the Kennedy family, the Shriver family holds a much longer place in American history, dating back to the Revolutionary War, Civil War, and even the signing of the Maryland’s Constitution and Bill of Rights. How do you think that his family’s place in history affected Sarge’s personality? How do you think that it affected Sarge’s perspective on everyday life and on major life events, such as his father’s financial ruin in the Great Depression? Do you think that it had any effect on Sarge’s ability to see the long-term viability of projects like the Peace Corps and the War on Poverty?

12. Sarge was repeatedly called upon to bring complex new ideas from conception to fruition, ideas such as the Peace Corps and the War on Poverty. There are many reasons for Sarge’s success in this type of task, including his inescapable optimism, can-do attitude, and his ability to see success where others lacked vision. Where do you think Sarge acquired the vision he used to see these projects through? What role do you think that his past played in that ability to see success? What role did his faith play? How do you think that these characteristics, or others, were important when Sarge was called upon to organize John F. Kennedy’s funeral and other monumental family tasks?

13. Sarge describes the impact of Peace Corps workers as “bringing peace on earth. Not the abstract kind of peace that politicians talk about, but the peace that men feel in their bones when they are loved, or fed, or clothed, or housed.” What are the differences between the two types of peace? Can one be achieved through the other? Do you think that world peace can be achieved through programs such as the Peace Corps?

14. On page 165, Mark describes his disappointment in himself for letting others down when he loses the race for the House of Representatives. Mark laments that he can’t bounce back from his loss and disappointment the way that his father did after his loss in the race for vice president. Do you think that Mark, who was a child at the time, understood or perceived Sarge’s emotions after the vice presidential loss? What do you think that Sarge was thinking or feeling after losing the campaign?

15. On page 190, Mark wants to ask his father, “Do you know what has become of you?” What answer would have made Mark feel better? What answer would you want – for yourself, or for a loved one? What does it mean to trade awareness for ignorance in his situation?

16. Sarge suffered several defeats in his life, including a very public loss of the vice presidency and an aborted campaign for governor of Illinois. By some measures, Sarge’s life would not have been considered as successful as some of his more famous in-laws. Would you consider his life successful? Why? What is his definition of success?

17. Mark declares that he does not try to live up to his father, expressing the futility of such a goal. Yet on page 202, Mark says that Sarge’s “example haunted me; I wanted to believe like he did, love like he did, but I felt I was falling short of the mark.” How is living up to his father and living like him different? How is it the same?

18. Having a famous father can be difficult for anyone trying to find his own identity. Mark was in the less common situation of having, in addition to a famous father, a famous mother, and an even more famous extended family. Do you think that having multiple famous relatives, rather than his father as the sole family icon, made it easier or harder to form his own identity? Did the unusually high bar for accomplishment set by multiple members of Mark’s family alter his own definition of a successful life? Does being surrounded by so many great achievements make achievement more or less special?

19. Despite seeing the enormous burden that financial ruin put on his own father, Sarge did not appear to be focused on the accumulation of wealth. What effect do you think his father’s ruin had on Sarge? How do you think that this effected his perception of personal wealth in relation to self-worth?

20. Mark admits many shortcomings, including a lack of patience, when it comes to caring for his father. How would you have dealt with the situation differently?