355: The Women of Washington’s Spy Ring Topics and Questions for Discussion:

• Who was your favorite character: Meg, Elizabeth, or Sally and why?

• One of the major themes of 355 is sacrifice. Who sacrificed the most in the novel and how did what they did for the war change them?

• For those fans of Brodway’s Hamilton, the Musical, compare and contrast how the following characters were portrayed in the musical and 355: Hercules Mulligan, Aaron Burr, George Washington and Alexander Hamilton

• Between killing Alexander Hamilton and being charged with treason, Aaron Burr had a reputation for being a scoundrel later in life. How did you feel about him when he first met Meg? Do you agree with the reason he broke up with her—because he wanted to go to war— right before Meg returned to her father?

• Twenty years after meeting Aaron Burr, Meg declared she would have been a thousand times happier with her life had she been allowed to be with him. Do you think they would have lived happily ever after if Meg hadn’t left?

• The home where Peggy was brought after Benedict Arnold was declared a traitor belonged to Theodosia Prevost. Although Theodosia was married to a British officer, Aaron Burr was a regular guest, and the two ended up marrying after her husband died of yellow fever. Compare Theodosia to Meg.

• Many historians claim that Peggy Shippen faked her nervous breakdown. As stated in the Epilogue of 355, Aaron Burr stated that Peggy Shippen played an active role in Benedict Arnold’s treason. How is Peggy portrayed in the novel? Do you think she was as guilty as her husband?

• Do you think Sally and John Andre would have ended up together if Andre hadn’t been killed? Why or why not?

• How did you feel about John Graves Simcoe in the novel? As stated in the Epilogue, Simcoe went on to play a central role in the abolition of slavery in Canada after the war. Is this in line with his character?

• How did you feel about Elizabeth making the decision to get the smallpox vaccine giving the dangers it presented? Would you have done the same?

• Who was more of a likeable male lead—Robert Townsend or John Andre? Why?

• SPOILER ALERT: The novel takes the view that Sally was the 355 (woman) that Abraham Woodhull stated could “outwit them all.” How did Sally manage to outwit the British? Would she have been able to play such a central role without her brother’s help?