The Prince by Niccolò Machiavelli


Just for Fun

How Machiavellian Are You? -- Developed by psychologists in the sixties, this 20-question quiz asks you to evaluate specific statements. Be prepared to discuss. Also known as the Mach IV Test. Online version.

“Bill, Meet Niccolò” from U. S. News & World Report offers some Machiavellian advice to then President Bill Clinton.

“Dear Vladimir: Congratulations. You Read My Book” from The Wall Street Journal purports to be a letter from Machiavelli to Putin.

The Municipal Machiavelli is a quirky blog that rewrites The Prince for municipal politicians. Yes.


Niccolò Machiavelli


Leo Rosten’s Biography from the Look magazine series, “They Made Our World,” is a masterpiece in itself. I remember reading it as a seventh-grader and hunted it down. It is my pleasure to share this jewel with you.

Graphic Novels

There are two graphic novels available for The Prince.

Don MacDonaldDon MacDonald offers a historically accurate graphic novel, hand drawn and hand painted..

Learning to Love Machiavelli is his TED Talk, discussing how he tries to address misconceptions about Machiavelli in his graphic novel.

Free posters of several quotes are available.

Shane ClesterShane Clester’s version uses a black-and-white cartoon style in which a dark, brooding Machiavelli addresses a child prince. Covering major portions of the text, Clester adds his own interpretations, visual subtexts, and modern translations. Available from Amazon.

Patrick Curry


Patrick Curry’s Graphic Guide, part of a series that introduces philosophy is an easily accessible manner, focuses on main concepts, analysis, and application to modern times and political concepts, even communism and liberal democracy. Hard to find, but worth a look.



“The Modern Machiavelli” from The American Thinker discusses six major tenets and applies them to contemporary politics.

“Why Machiavelli Still Matters” from the New York Times briefly places the book in contemporary perspective.

“Machiavelli Was Right” in The Atlantic includes references to the death of Osama bin Laden.

“The Florentine: The Man Who Taught Rulers How to Rule” by Claudia Roth Pierpont is an in-depth analysis from The New Yorker.

“The Cunning Critic of Political Reason” discusses Machiavelli’s legacy.

“Machiavelli’s Enterprise” from The New Criterion is a lengthy analysis and overview.

“That’s What Machiavelli Can Teach Us” from The New Statesman applies Machiavelli to British politics, focusing on Tony Blair.

“American Presidential Machiavellianism” applies the Mach IV scale to American presidents from Washington to Reagan. Oddly interesting.

“The Prince Wants a Word With You” reviews The 48 Laws of Power, a modern version.

For the very literary, Robert Denham analyses Northrop Frye and Niccolò Machiavelli. A very selective audience.


Full Text from Learn Out Loud

Subscribe to an iTunes podcast from Books Should Be Free.


Brief Introduction to The Prince from Macat (3 min). Very simple.

Animated Book Review from Fight Mediocrity (10 min).

Discovery Channel Great Books series offers the very best introduction to The Prince and its lasting impact. Though ony one hour long, it touches on mahor concepts and uses current evbents to connect to the text. Sometimes available on YouTube (though perhaps illegal), it is worth buying the DVD. Lesson Plan.

Salman Rushdie’s Machiavelli’s Bad Rap defends the author’s democratic desires.

Learning to Love Machiavelli is Donald MacDonald’s TED Talk and is as wonderful as most TED Talks are.

Who’s Afraid of Machiavelli? from the BBC includes reference to the Mach IV test, exerpts from the text, and modern applications.

School of Life focuses on a short political analysis in Political Theory -- Niccolò Machiavelli.

Top Twenty Machiavelli Quotes as a YouTube video.



“At 500, Machiavelli’s The Prince Still Inspires Love and Fear” on NPR introduces the work and its impact (5 min).

Nigel Warburton’s podcast on The Prince serves as an insightful introduction to the main principles (14 min).

Machiavelli: Devil or Democrat? assesses Machiavelli on the 500th anniversary of the work (28 min).

In Our Time: Machiavelli and the Italian City States from the BBC analyses in depth, focuing on placing the book in a historical context (40 min).

University of Oxford podcast Machiavelli’s The Prince 500 Years On (50 min). Very detailed and thorough.

Machiavelli on Politics from the Partially Examined Life is a bit comic and rambling (1:33 min). Discussion among several speakers.

The Prince’s Podcast applies the writings of Machiavelli to modern politics (40 min). Discussion and topics are wide-ranging.


Chapter Questions (50) include only a few for each chapter, but cover the whole text.

Discussion Questions focus on main ideas. Interpretive.

Claims & Proof asks students to agree or disagree with nine quotes, citing evidence for their opinions. Could work as an introduction to main ideas or even independently of the text.

Paraphrase & Analysis includes a creative component.

Quotation Interpretation & Application asks students to find real life examples for at least five of the quotations.

Text to Text from The New York Times has an excellent unit comparing exerpts from The Prince to the NYT article “Why Machiavelli Still Matters.”

Analysis & Essay designed as an essay focused on applying Machiavelli to currnt events.

Critique focuses on student opinions, but requires evidence to support those opinions.

MIT All-School Read Questions & Essay are challenging, but very tightly focued.


My Handouts

Chapter-by-chapter, these 150 questions are useful for student presentations and discussions on individual chapters (I am not likely to grade 150 questions per student ever).

Comprehension Questionsfocuses on twenty major questions (I am likely to expect each student to answer every one of these.

Composition Exam on the book as a whole has only four parts and focuses on analysis and application.


Commentary on The Prince -- A collection of comments on the impact of the text. Worthy of analysis and discussion.

Teaching Machiavelli, or How I Learned to Love The Prince from English Journal is inspirational for me. Some parts are directly useful for students as well.


Quotes has 50 quotes from the text, each on a separate slide.

Excellent Interactive Presentation that includes bellwork, brainstorming, and application questions.

Activities that include journal responses and quote analyses.

Machiavelli Today applies main concepts to current events.

A Comparison/Contrast of The Prince and The Courtier.

An Introduction and an Analysis


Teacher Guides

Arts of Liberty Project, known for its Literature resources, has a general overview Study Guide, designed to promote discussion of major ideas (4 pages).

Lit Charts Study Guide for Students includes themes, quotes, close reading, symbols, and “characters” referenced in the book (50 pages). The Teacher Guide provides chapter by chapter worksheets (with answers) for all these. Reasonably priced and very detailed.

The Penguin Guide is short with only a few questions on major points.


  • As an introduction to the DBQ process, this handout uses one short exerpt from The Prince to introduce the process of document analysis.
  • Also an introductory approach, this Absolutism DBQ from Holt includes specific DBQ questions for eight shorter documents.
  • Absolutism and Democracy is a DBQ that uses six more difficult exerpts to introduce a true AP-style DBQ. Includes a PowerPoint.
  • A teacher-constructed DBQ on the Renaissance includes Machiavelli.


Creative Projects

The Enriched Classics Curriculum Guide includes lessons and handouts for five projects:
• A travel brochure for Florence, Italy, in the year 1500, puts the text in historical context.
• Role-playing a lion, a fox, and or a wolf.
• Language Analysis of the term Machiavellian.
• Charting quotes that show the good / evil contradictions in Machiavelli’s advice.
• Applying Machiavelli’s advice on war to contemporary situations.

Wanted Poster & Rubric designed for the ideal Machiavellian leader.

Presidential Advice asks students to role-play Machiavelli and give advice to the new US President.

Letter to a Leader asks students to select a leader and target Machiavelli’s advice to that leader.

Modern Leader Analysis requires students to analyze a major European leader who has had power in the last thirty years.

Personal Reflections includes both a written response and an artifact to illustrate student reflections on the text and its application.

Characteristics of Candidates is quirky activity for discussion, listing characteritics of several unnamed people. Students discuss leaderrship potential of each. Revelations of the real people described serves as a springboard for discussion or writing.

Back to Assignments or Home.
Updated 3 September 2020.


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