1. What do you consider to be Frank MacLeod’s defining characteristics? Is he a reprehensible murderer, a tragic figure, neither, or some combination? Is he worthy of readers’ sympathy? Why or why not?
2. How a Gunman Says Goodbye’s cast of characters (here) encompasses a wide swath of people on opposite sides of the law. Overall, who was your favorite character? Whom did you like the least?
3. What about Mackay’s portrait of organized crime surprised you? Overall, would you say his novels play against genre conventions or embrace them? What themes did you encounter about crime and criminality in the pages of How a Gunman Says Goodbye?
4. Were you surprised by the trajectory of Calum MacLean’s story in this book? Would you say he’s grown as an individual during the course of this novel? What do you think the changes Calum has undergone, if any, will mean for his future?
5. How would you compare Frank MacLeod with Calum MacLean? Who is the more formidable killer? Is one more sympathetic than the other? More moral? Age aside, would you say the two hitmen are more similar or different?
6. What do you think of Frank’s final act in How a Gunman Says Goodbye? Is this the pathetic surrender of a man with nowhere left to turn, the triumph of a man committed to his employers and his life’s decisions, or both?
7. What did you think of Calum’s relationship with Emma Munro, and of this recent development in his life? In Emma’s shoes, would you have pressed for more information about Calum’s profession sooner, or does Emma ask as soon as one reasonably might, given what she knows when? What do you make of the ultimatum Emma offers Calum, once she’s reasonably sure of the truth? Would you have made the same offer?
8. Discuss Peter Jamieson’s friendship and working relationship with Frank MacLeod. Do you think Jamieson makes the right decision to bring Frank back on the job in the novel’s opening pages? How well do you think Jamieson handles the attempt to change Frank’s role in his organization after the botched hit? Does Jamieson treat him with the necessary respect, given his years of service, or does he fail to do so? Do you agree with John Young that Jamieson has made the right decision about what to do with Frank in the end?
9. What do you think the immediate future holds for Calum MacLean? What are his intentions, and do you think he’ll be able to realize those goals? Ultimately, do you think Calum will meet the same fate as Frank MacLeod? Why or why not?