The Prince

Study Guide
Student Copy

To fully understand the questions in this unit, it is necessary for the student to review the
brief biography of Machiavelli included with the unit. This biography addresses some of the
political and personal motivations that may have triggered Machiavelli’s opinions regarding
a Prince’s use of military force, the qualities of a good leader, and the necessity of a Prince
gaining the good will of his subjects.

Dedication - To the Magnificent Lorenzo Di Piero De’ Medici

Vocabulary
antiquity – history; ancient times
extrinsic – additional features; unrelated, irrelevant
allurements – attractions
eminence – greatness
malignity – hatred

1. What prized possession does Machiavelli give the Prince, hoping to please him?

2. Machiavelli writes that to “understand the People a man should be a Prince, and to
have a clear notion of Princes he should belong to the People.” (Pg. 11) What does this
passage tell the reader about Machiavelli’s qualifications to write this book?

3. Machiavelli dedicated this book to Lorenzo Di Piero De’ Medici. In 1512, Machiavelli
was removed from his high government position when the Medici family assumed
absolute power of Florence. Then, in 1513, Machiavelli was falsely accused of
conspiring against the Medici family. As a result of these accusations, Lorenzo had
Machiavelli imprisoned. Some critics believe the last paragraph of the dedication is a
cleverly concealed insult to Lorenzo. Others believe Machiavelli is writing this book to
gain a government position in the new, Medici-controlled government. Which opinion
do you support and why?

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Chapter I - Of the Various Kinds of Princedom, and the Ways in Which They
are Acquired

Vocabulary
sovereignty – authority

1. Define a hereditary Princedom.

2. What are the two types of new Princedoms?

Chapter II - Of Hereditary Princedoms

Vocabulary
usurper – a person who seizes something as his or her own
odious – hateful
efface – to destroy; erase
dovetail – a piece of an interlocking joint; a perfect fit

1. In what ways is a hereditary Princedom easier to maintain than a new Princedom?

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Chapter III - Of Mixed Princedoms

Vocabulary
vexations – irritations
insolence – rudeness
scruple – to hesitate
wrest – to take by force
discordance – a disagreement, conflict
efficacious – effective
tenure – holding a position or occupation permanently
abode – a home
disaffected – discontent; resentful
expedient – a solution; plan
unmolested – undisturbed
formidable – strong
hitherto – up till now; so far
subjection – ruled by others
conciliated – satisfied
diligence – a steady effort
inchoate – immature
sagacious – having sound judgment, wise
maxim – a fundamental truth
valour – courage
obliged – indebted
temporal – natural; as opposed to spiritual
aggrandized – made more powerful
tributary – a contributory
ensue – to follow, pursue
dominions – territories
ceded – yielded
allege – to state; assert
dissolution – termination
statecraft – the art of leading a nation
wrought – created; produced
axiom – truism

1. Why can the new Prince of a mixed Princedom not avoid offending his new subjects?

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2. List the two things a new Prince must do to keep a new Princedom that is joined to his
older Princedom.

3. Machiavelli supports his conclusions on the way a Prince needs to conduct himself by
citing a true example that would have been familiar to Lorenzo Di Piero De’ Medici.
Who is this bad example and why is his Princedom a failure?

4. Why is it a good idea for a Prince who acquires a new Princedom to travel to the new
land and reside there?

5. What are colonies? Why are they better than troops at keeping order in a new State?

6. Why does Machiavelli suggest that the new Prince should conciliate the weaker powers
in the new State and humble the already existing leaders?

7. For what reasons does Machiavelli stress that war is not to be avoided?

8. Why does Machiavelli not support the maxim, “Leave it to Time”? (Pg. 21)

9. What example from the politics of the time does Machiavelli give to support the axiom,
“He who is the cause of another’s greatness is himself undone”? (Pg. 23)

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Chapter IV - Why the Kingdom of Darius, Conquered by Alexander, Did Not,
on Alexander’s Death, Rebel Against His Successors

Vocabulary
thither – abroad
precedence – a preference; priority
defection – abandonment, desertion
extirpated – removed; exterminated
procure – to obtain; acquire
acquisitions – accomplishments, achievements

1. List the two ways Princedoms are governed.

2. Why is a Princedom governed by a sole Prince difficult to conquer but easy to hold once
it is won?

3. Machiavelli uses France as an example of a Princedom with hereditary Barons or nobles

as part of the government. Why does Machiavelli believe France is easy to conquer but
difficult to rule?

4. How do Alexander and the Romans manage to hold onto their powerful empires?

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Chapter V - How Cities or Provinces Which Before Their Acquisition Have
Lived Under Their Own Laws Are to Be Governed

Vocabulary
servitude – slavery
vitality – liveliness

1. List the three methods a newly acquired State, which is accustomed to living under its
own laws, can be held by the new Prince.

2. Which of these three methods of maintaining power in a newly acquired state does
Machiavelli think gives the new Prince the best chance of holding onto his power? Cite
historical references from the text to support your answer.

3. What does Machiavelli say about republics in this chapter?

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Chapter VI - Of New Princedoms Which a Prince Acquires With His Own
Arms and by Merit
Vocabulary
savour – a taste
alight – to come down; settle
presupposes – believes
oppressed – enslaved
enervated – sluggish
effeminate – weakened
virtuous – moral
adversaries – enemies
incredulity – skepticism
partisans – disciples
entreaty – begging, pleading
borne – equipped
fickle – inconstant

1. What is Machiavelli telling Lorenzo with the metaphor of the skillful archer who is
trying to hit a distant mark with his arrow?

2. Find a passage in the first paragraph of this chapter than might serve as an axiom that
anyone wanting to learn to be a leader should follow.

3. Define the word fortune as Machiavelli uses it in this chapter. In what sense does
Machiavelli think fortune contributes to a man’s greatness?

4. How does Machiavelli support the following statement from the book? “Hence it comes
that all armed Prophets have been victorious, and all unarmed Prophets have been
destroyed.” (Pg. 33)

5. In what way does the example of Hiero the Syracusan diminish the importance of
fortune to a leader’s success?

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Chapter VII - Of New Princedoms Acquired by the Aid of Others and by Good
Fortune

Vocabulary
hindrance – a barrier, obstacle
superfluous – excessive
annulling – invalidating
quelling – suppressing
desirous – wanting
fidelity – faithfulness
waywardness – unpredictability
desist – to stop
factions – opposing sides
partisan – members of a group
stratagem – a plan
ingratiated – brought into favor deliberately
tumult – a disturbance
Tribunal – the court
populace - the people; population
adherence – bond, unity
exigencies – urgent needs
despoiled – robbed
surmounted – overcome
affable – friendly
magnanimous – gracious, unselfish
resentment – ill will

1. Why do Princes who come to power suddenly through good fortune rather than by their
own merit have a difficult time holding onto their Princedoms?

2. How does Cesare Borgia obtain his Princedom? What measures does he take to hold
onto it?

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3. What happens to keep Borgia’s well laid plans from succeeding? Despite his problems
why does Machiavelli consider Borgia a “pattern for all such as rise to power by good
fortune and the help of others”? (Pg. 40)

4. Briefly describe the one error Machiavelli thinks Borgia makes; an error which “was the
cause of his ultimate downfall.” (Pg. 40)

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Chapter VIII - Of Those Who By Their Crimes Come to be Princes

Vocabulary
ascent – to rise
dregs – the bottom levels; residue
conjoined – mixed
vigour – energy
imparting – sharing; communicating
preconcerted – agreed upon
besieged – surrounded
ascribed – attributed
devoid – lacking
extricated – removed
resolute – firm
countenance – appearance
connivance – plotting
patrimony – heritage
endeavour – an honest effort
repast – food
constrained – forced
ordinances – laws
parricidial – parental murder
villany – underhandedness
perilous – dangerous
timidity – shyness
vicissitude – a chance
adversity – a hardship
leniency – having mercy, tolerance; forgiveness
compulsory – required

1. What does Machiavelli say regarding Hamilcar’s actions and their relationship with
Fortune?

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2. What are the “means which may lead to power, but which confer no glory” on the
Prince? (Pg. 42)

3. Briefly describe the events in Oliverotto of Fermo’s rise to power which prove the
following axiom: “Injuries, therefore, should be inflicted all at once, that their ill savour
being less lasting may the less offend; whereas, benefits should be conferred little by
little, that so they may be more fully relished.” (Pg. 44)

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Chapter IX - Of the Civil Princedom

Vocabulary
attainment – an acquirement
astuteness – keenness; discrimination
Licence – excessive freedom
pusillanimity – a lack of courage
prudent – conservative
conciliate – to appease
beholden – indebted
benefactor – a protector; provider
controvert – debate; contradict
saw – an old saying
mire – mud
magistrates – judges
juncture – crossroads

1. List two ways to obtain a Civil Princedom.

2. Why is it essential that a Prince maintain a friendly relationship with the people he
governs?

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Chapter X - How the Strength of All Princedoms Should be Measured

Vocabulary
exhort – to urge
circumspection – acting with caution, discretion
averse – reluctant, hesitant
tedious – boring; repetitious
ramparts – defenses, fortifications
victual – food
sinews – strength
leaguer – encamped for battle
protracted – drawn-out
siege – an attack
dexterously – skillfully
ardour – passion
abated – decreased
incur – to take on, acquire

1. Briefly discuss the difficulties an enemy will face if he tries to attack a town that is well
fortified by a Prince who is liked by his people. What historical proof does Machiavelli
offer in support of his ideas?

2. List three ways a Prince can insure the loyalty of his people during a yearlong attack that
destroys their possessions outside of the town.

3. Find a passage in this chapter that might be called an axiom; point out the importance
of fortifications to help a Prince maintain his power.

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Chapter XI - Of Ecclesiastical Princedoms

Vocabulary
ecclesiastical – relating to religion
venerable – honorable; respectable
efficacy – potency
inasmuch – concerning
presumptuous – assuming, overconfident
potentates – rulers
pontiff – a religious authority; the Pope or a Bishop
insubordination – disobedience, defiance
foment – to provoke; inspire
dissension – a conflict, disagreement
prelates – high-ranking clergymen; bishops
discord – a disagreement
papacy – the office of the Pope
benignity – grace

1. Why does Machiavelli state that ecclesiastical Princedoms “alone are secure and happy”?
(Pg. 51)

2. In general, what is Machiavelli’s evaluation of the “temporal authority” of Popes?

(Pg. 52)

3. Cite incidents from the chapter to support or refute the following statement: Machiavelli
applauds the efforts of Pope Alexander and Pope Julius to gain wealth and power for the
church by conquering Romagna, Bologna, and the Venetians as well as for expelling the
French from Italy.

4. The last paragraph in this chapter is boldly flattering to Pope Leo. What do you think
this reveals about Machiavelli’s motivation to write The Prince?

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Chapter XII - How Many Different Kinds of Soldiers There Are and of
Mercenaries

Vocabulary
mercenaries – hired soldiers
discourse – a discussion
auxiliaries – recruits
insolent – defiant
plundered – robbed
paltry – insignificant
untoward – unruly
well-nigh – nearly
forsook – abandoned
repute – to regard
arbiters – judges
retinue – a group
sortie – a rally

1. List five adjectives Machiavelli uses to describe the useless and dangerous qualities of
mercenaries.

2. In what way does the example of the Venetians support Machiavelli’s contention that
a Princedom is better off with an army made up of its own subjects. Also support his
contention that a Princedom that relies on mercenaries is poorly defended?

3. Briefly describe the military rules the mercenary troops follow that makes them terrible
soldiers.

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Chapter XIII - Of Auxiliary, Mixed, and National Arms

Vocabulary
infidel – one who does not have any religious beliefs
inertness – an inaction
eschewed – gotten rid of
discern – to identify
ascertained – concluded

1. Define the terms auxiliary troops, mixed troops, and national arms.

2. Why is it dangerous for a Prince to rely on auxiliary troops to defend his state?

3. Machiavelli likes to use Cesare Borgia as a good example of how a Prince should rule.
Briefly describe why Cesare Borgia is a model for Machiavelli’s argument that native
troops are the best.

4. What is Machiavelli’s opinion of mixed troops? Briefly relate why King Louis is again
given as a poor example of leadership.

5. In what ways might Machiavelli be trying to influence Lorenzo’s rule of Italy when he
writes,
“But from want of foresight men make changes which relishing well at first do not betray their
hidden venom, as I have already observed respecting hectic fever. Nevertheless, the ruler is not
truly wise who cannot discern evils before they develop themselves, and this is a faculty given to
few”? (Pg. 63)

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Chapter XIV - Of the Duty of a Prince in Respect of Military Affairs

Vocabulary
calamities – disasters
renown – a reputation
reproaches – criticisms
proportion – a balance
retainers – employees
commendations – acknowledgements
contingencies – possibilities
chastity – a virtue
affability – friendliness
conformed – adapted
idle – still

1. What are the consequences for a Prince who is ignorant of military affairs?

2. List the two ways a Prince must prepare himself for war even in times of peace. Briefly
describe the advantages of each.

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Chapter XV - Of the Qualities in Respect of Which Men, and Most of All
Princes, are Praised or Blamed

Vocabulary
fanciful – foolish
avaricious – greedy
haughty – overly proud
facile – easy
frivolous – unimportant
devout – religious
laudable – worthy
infamy – negative fame

1. Why does Machiavelli suggest that it is “essential, therefore, for a Prince who desires to
maintain his position, to have learned how to be other than good, and to use or not to
use his goodness as necessity requires”? (Pg. 69)

2. Find a passage in this chapter that might be considered an axiom stating that a Prince
must learn what cruelties are necessary for the good of the state and that these are
acceptable to the people and will quickly be forgiven.

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Chapter XVI - Of Liberality and Miserliness

Vocabulary
miserliness – stinginess
reputed – known for
sumptuous – showy
confiscations – seizing property
impoverished – poor
esteem – to respect
endeavouring – attempting, trying
parsimony – stinginess, thriftiness
levying – demanding
expenditure – spending
forbear – to refrain
contempt – hatred
rapacious – ravenous
retrenching – cutting
lavish – extravagant
ignominy – dishonor
reckoned – assessed

1. In what ways does a Prince who is liberal incur the hatred of his subjects?

2. List one historical example Machiavelli offers to support his contention that a Prince
who accomplishes great things is miserly.

3. How can a Prince be liberal without harming himself or his subjects?

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Chapter XVII - Of Cruelty and Clemency, and Whether It Is Better to be
Loved or Feared

Vocabulary
clemency – the act of showing mercy
imputation – the accusation
rapine – to seize with force
temper – to strengthen
apprehension – hesitation
manifest – obvious
mutiny – a rebellion
transcendent – unmatched
marred – damaged

1. When is it necessary and acceptable for a Prince to be cruel?

2. List the qualities of human nature that make it safer for a Prince to be feared than to be
loved.

3. What steps must a Prince take to avoid being hated? Find a passage in this chapter
which serves as an axiom on how to avoid being hated.

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Chapter XVIII - How Princes Should Keep Faith

Vocabulary
toils – struggles
plausible – reasonable
solemn – sober; thoughtful
dissembling – pretending
dupes – victims
asseverating – declaring
enumerated – counted
replete – rich with
embodiment – the epitome, essence

1. How does the myth of Chiron the Centaur help Machiavelli prove his statement that “a
Prince should, therefore, understand how to use well both the man and the beast”?
(Pg. 79)

2. When does Machiavelli think it is acceptable for a Prince to break his promises?

3. List two negative traits Machiavelli sees in humanity that make it possible for a Prince to
be a hypocrite and still maintain his power.

4. What five qualities does Machiavelli believe a Prince must appear to have? Why is it
important for a Prince to succeed in establishing and maintaining his authority even if
he must employ less than honorable tactics?

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Chapter XIX - That a Prince Should Seek to Escape Contempt and Hatred

Vocabulary
pusillanimous – cowardly
irresolute – indecisive, undetermined
irrevocable – irreversible
cajoling – coaxing
reverence – having great respect
discontented – unsatisfied
detestation – hatred
arbitrator – a mediator
devolve – to delegate
deposed – removed from office
conspired – plotted, planned
humours – temperaments
revered – respected
licentious – wild; undisciplined
indolent – lazy
artifice – trickery
odium – hatred
contemning – despising
sate – to satisfy
imperial – royal
disposition – character
concurred – agreed
render – to make
disdain – hatred
atrocities – acts of inhumanity
perpetrated – committed
prefect – an officer or official
contrived – planned
Sovereign – a ruler

1. What must a Prince do when dealing with his subjects to appear wise, strong, and
courageous?

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2. What are the two dangers to which a Prince is exposed? How can he avoid them?

3. Why does Machiavelli use France as an example of a kingdom that successfully balances
the needs of the nobles with the needs of the common people?

4. What qualities of leadership does Septimius Severus possess that make him a good
example of how to rule?

5. How does Caracalla cause his own ruination by not adhering to the following guideline?
“The only precaution he can take is to avoid doing grave wrong to any of
those who serve him, or whom he has near him as officers of his Court.” (Pg.
89)

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Chapter XX - Whether Fortresses, and Certain Other Expedients to Which
Princes Often Have Recourse, are Profitable or Hurtful

Vocabulary
imputations – insinuations, accusations
wont – accustomed
fomented – excited, provoked
vanquishing – defeating
razed – demolished
citadel – a fortress
insurgents – rebels
succour – assistance; help

1. Why is it better for a new Prince to arm his subjects than it is for him to try to disarm
them?

2. For what reasons does Machiavelli disagree with the principle “Pistoja was to be held by
feuds, and Pisa by fortresses”? (Pg. 94)

3. What does Machiavelli think is a Prince’s best defense against enemies?

4. In what ways could the following advice be considered self-serving for Machiavelli?
“…those men who at the beginning of a reign have been hostile, if of a sort
requiring support to maintain them, may always be won over by the Prince
with much ease, and are the more bound to serve him faithfully because they
know that they have to efface by their conduct the unfavorable impression he
had formed of them.” (Pg. 95)

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Chapter XXI - How a Prince Should Bear Himself So as to Acquire Reputation

Vocabulary
pious – religious
exploit – a deed
stanch – firm
legate – a spokesman
envoy – a representative
aloof – separate, apart
ingratitude – ungrateful
mercantile – relating to trade
munificence – generous

1. In this chapter Machiavelli gives a new Prince some advice on how to conduct himself
so he gains the reputation of a great leader. In what ways does Ferdinand of Aragon
serve as a good example of leadership?

2. What behavior is Machiavelli encouraging in the following excerpt from this chapter?
Do you think he is contradicting an earlier chapter where he states that a Prince must
learn to be “other than good”?
“it greatly profits a Prince in conducting the internal government of his
State, to follow striking methods…and to choose such ways of rewarding and
punishing as cannot fail to be much spoken of. But above all, he should strive
by all his actions to inspire a sense of his greatness and goodness.” (Pg. 98)

3. Find a passage in this chapter stating that a Prince must be decisive and take sides in a
conflict rather than staying neutral.

4. Why is it dangerous for a Prince to align himself with someone who is stronger than
himself?

5. List two things a Prince must do for his subjects which do not deal with war.

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Chapter XXII - Of the Secretaries of Princes

Vocabulary
conjecture – an inference, assumption
burthens – burdens

1. Briefly define the three levels of intelligence for a Prince’s advisors. Into which one of
these categories do you think Machiavelli places himself?

2. What is a “good minister” according to Machiavelli? How should the Prince reward a
good minister?

Chapter XXIII - That Flatterers Should Be Shunned

Vocabulary
shunned – ignored
incurring – acquiring
vacillating – swaying
obtruding – imposing
reconcile – to make peace
rogues – untrustworthy and unreliable people

1. In what ways should a Prince accept council from his advisors?

2. In what sense can the last paragraph in this chapter be considered ironic?
“Hence it follows that good counsels, whencesoever they come, have their
origin in the prudence of the Prince, and not the prudence of the Prince in
wise counsels.” (Pg. 104)

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Chapter XXIV - Why the Princes of Italy Have Lost Their States

Vocabulary
sanction – an approval
felicity – happiness
defence – (British) defense
contemplate – to reflect on
ignoble – common

1. List the three errors the previous rulers of Italy have made which have lost them their
dominions in Italy.

2. What is Machiavelli’s opinion on the role of “fortune” in the loss of these states?

3. Why is it folly to hope the people will restore a Prince to power when they become
“disgusted with the arrogance of the conqueror”?

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Chapter XXV - What Fortune Can Effect in Human Affairs, and How She May
Be Withstood

Vocabulary
torrents – downpours
weirs – a dam
moles – a breakwater
inundation – a flood
impetuosity – impulsive
subtlety – elusive
propitious – fortunate
menaced – annoyed
congruity – an agreement
audacity – boldness

1. How much free will does Machiavelli believe men have and how much of their lives is
determined by the whims of “fortune”?

2. In what way can a Prince fortify himself so he will not be ruined when fortune turns
against him?

3. Find a passage in this chapter that personifies Fortune as a woman.

4. List two general rules a Prince may follow to secure good Fortune.

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Chapter XXVI - An Exhortation to Liberate Italy From the Barbarians

Vocabulary
pre-eminent – superior
manna – spiritual or divine nourishment
rout – to defeat
homage – honor
ennobled – honored
auspices – protection
strife – a struggle

1. In what sense is this last chapter different from the earlier chapters in terms of the tone
of the writing and the purpose of the text?

2. Who is the “she” mentioned in the following passage? Why might this plea for Lorenzo’s
help be well received by the Prince?
“We see how she prays God to send some one to rescue her from these barbarous cruelties and
oppressions.” (Pg. 112)

3. What argument does Machiavelli use to convince Lorenzo of the wisdom of using Italian
troops for his army?

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