--theme--

1. "If Benedict Arnold hadn't faced the hardships he did in his youth due to his family's fall in
societal status, would his desire for recognition and status still have led him to treason? How
could his life have possibly unfolded differently if he had received the recognition he desired?"
2. "The rivalry between Arnold and Ethan Allen, and later Arnold and General Horatio Gates,
had significant impacts on the course of events. How might Arnold's choices and trajectory have
diverged if these rivalries did not exist?"
3. "Looking at Arnold's motivations through the lens of revenge, what other options or choices
could he have made to address his feelings of resentment that could have avoided an act of
treason?"
4. "Delving deeper into the character of John André, what alternative paths could he have
pursued to alleviate his feelings of resentment against the Americans without resorting to aiding
and abetting treason?"
5. "Treason has devastating consequences for all involved – the act disgraces the traitor, harms
the betrayed, and alters the course of history. Based on the events demonstrated in The Notorious
Benedict Arnold, how might these outcomes have been prevented or mitigated despite the
conflicts, rivalries, and personal ambitions presented?"

1. "Explore how Benedict Arnold's relentless ambition to elevate his status influenced his
decisions, actions, and ultimate downfall. How might history remember him differently if he had
pursued his ambition differently?"
2. "Analyze how rivalry played out in shaping early American conflicts in the narrative and
reflect on how these rivalries impacted the larger story of the American War of Independence."
3. "Considering Benedict Arnold and John André's feelings of revenge, how did these emotions
blind their judgment and lead to treacherous acts? Can revenge ever be justified in their
circumstances?"
4. "Discuss the psychological, morale, and trust injuries inflicted by Arnold's treason on his
comrades and the American freedom cause. What could have been a potential solution to limit
this kind of betrayal?"
5. "Arnold and André both suffer from a sense of not being recognized or appreciated. How does
this feeling guide their decisions throughout the book and how might things have turned out
differently had they found recognition in positive, not destructive ways?"

Question 1: In The Notorious Benedict Arnold, the ambition of several characters

plays a key role in shaping their actions. Can you analyze the ambition of a character
such as Arnold or André as a class impetus and the means they took to rise? Would
their paths differ if they were in a different time or context?
Question 2: From Arnold and Allen's rivalry to that of Arnold and Gates, the book
seems dominated by these interpersonal frictions. Can you identify the motivations
behind their rivalries and reflect on how these rivalries pushed the course of early
American conflict? What could have changed if these rivalries were resolved
constructively?
Question 3: Revenge often acts as a blinding motivator for characters like Arnold and
Andre in the book. Think about the role revenge played in Arnold's life decisions.
Would his actions have been different if he had chosen forgiveness over revenge?
Discuss possible alternative paths.
Question 4: The theme of 'devastation of treason' is very dominant in The Notorious
Benedict Arnold. how do you think the events and Arnold's actions impacted the
perception of loyalty and treason during that time, in light of his betrayal to his
country and his former cause? Would his actions have been seen differently in a
different era?
Question 5: The theme of ambition also played a significant role in Gates' life. Reflect
on whether Gates' actions driven by ambition had a positive or negative impact on
early American conflict. What could Gates have done differently if power and status
were not his prime motives?

--figure--

1. "Putting yourself in Benedict Arnold shoes, can you understand his reasons for
turning traitor? Get inventive and devise an alternative scenario where Arnold
manages to address his grievances and dissatisfaction without resorting to treachery.
What would be the various steps and factors to consider?"
2. "John André and Benedict Arnold share a relationship driven by shared ambition
and shared downfall. Can their association be viewed as a cautionary tale about the
dangers of unchecked ambition? What paths could they have pursued to channel their
ambition in less destructive ways?"
3. "George Washington is known for his restraint and patience, even in the face of
betrayal. Could he have done anything differently to prevent Benedict Arnold from
defecting? Speculate on how he could have utilized his leadership skills to change
Arnold's trajectory."
4. "Peggy Shippen found herself in the middle of the notorious betrayal carried out by
her husband, Benedict Arnold. What do you think could have motivated her to support
him? Discuss her potential reasons and the alternative decisions she could have taken
that would alter the overall outcome of the story."
5. "Sir Henry Clinton played a significant role in the narrative, engaging in decisions
that shaped the course of events. What strategies would you propose that Clinton
could adopt for a different outcome in the war, considering both the British and
American perspectives?"
1. "Benedict Arnold frequently craved attention and recognition, even at the expense
of his own character. Can you provide an example where this led to a problem for
Arnold? How could Arnold have handled this situation differently without sacrificing
his pride?"
2. "In the context of John André’s character, how do his high ambitions drive his
actions, and occasionally conflict with his personal interests? Could André’s attempt
for recognition have turned out differently, if so, how?"
3. "Benedict Arnold and George Washington had a complex relationship, tangled with
trust and betrayal. How do their interactions and the ultimate betrayal illuminate the
complexities of loyalty during wartime? How might Washington's attitude to Arnold
have been different if he was aware of Arnold's potential for treachery?"
4. "Discuss how Peggy Shippen's decision to marry Arnold, despite his controversial
reputation, might reflect the societal pressures or expectations of the time. What were
some alternative life decisions that she could have made that may have altered the
course of her life?"
5. "Considering Horatio Gates’ victory in the Battle of Saratoga and subsequent defeat
in the Battle of Camden, how would you evaluate his decision-making process in
crucial fights? What alternative strategies could Gates have employed in the Battle of
Camden to potentially change the outcome?"

1. "Considering Benedict Arnold's complex personality along with his desire for
action, respect, and acceptance, what alternatives could he have explored, real or
imagined, to achieve his goals without resorting to betrayal?"
2. "How could John André's ambition and desire for social status have contributed to
his downfall? Would a different approach have secured his success and survival?"
3. "Considering the moral complexities and ambiguities of George Washington,
explore alternative decisions he could have made at key points in his relationship with
Arnold. How might these decisions have impacted the course of events?"
4. "How do Peggy Shippen's actions and decisions reveal her personality and
character? What could she have done differently to potentially change the course of
her and Arnold's life?"
5. "Considering Joshua Hett Smith's role as an unwitting accomplice in Arnold's
treasonous plot, what steps could he have taken to better understand and assess the
true nature of the situation he found himself in?"

Essay Topics
1.
How does the structure and writing style of Sheinkin's book contribute to its
resembling an adventure novel? In what ways is the book stylistically
different from an academic historical work?

2.
Why do you think Sheinkin chose to open the book with a preview of John
André's execution, rather than with something relating directly to Arnold?
Do you find it to be an effective opening?
3.
Sheinkin's book claims that Arnold is “hopeless at political maneuvers.”
What are some instances that show Arnold's lack of diplomatic finesse?

4.
In what ways might Arnold's childhood experiences—particularly his
attitude toward authority—predispose him to take part in the American
Revolution?

5.
Do you think Arnold's decision to switch to the British side is selfishly
motivated, or was it—as he claims in his letter to Washington—motivated
by patriotism? Do you think his decision could be justified in light of the
progress of the war at the time?
6.
Does Arnold's treason come as a complete surprise, or is it foreshadowed by
any of his previous behavior and character traits?

7.
Sheinkin describes Arnold's defense of himself during his court-martial as
“self-righteous.” Do you agree? Do you think his complaints about “vile
prostitution of power” and “glaring tyranny and injustice” toward him are
justified?
8.
As governor of Philadelphia, Arnold comes in conflict with the
Pennsylvania council leader James Reed over the issue of what behavior
should be seen as political (for example, entertaining guests from the
Loyalist side). Discuss some issues or behaviors in contemporary society
which might be seen as political or apolitical depending on the context.
9.
Why do you think John André chose to identify himself as British when
stopped by the American militiamen on his way to New York? Might things
have gone differently if he had said he was American?
10.
Which side of Benedict Arnold—hero or traitor—has greater weight? Do
you think Arnold's deeds on behalf of the American cause should be
celebrated, or does his treason cancel out whatever good he may have done?