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Secondary sourcePaintinglate 16th century

Portrait of Niccolò Machiavelli

Santi di Tito · late 16th century

A late 16th-century portrait by Santi di Tito that became the standard image of Machiavelli, though painted after his death.

This posthumous portrait became the standard visual image of Machiavelli, despite being painted after his death.

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Painting of a man with short dark hair in a black cloak with red sleeves and red collar, resting one hand on a stone ledge and holding a book in the other hand against a dark brown background.
Santi di Tito, Portrait of Niccolò Machiavelli, late 16th century. Palazzo Vecchio, Florence.

About this source

What it is

This portrait of Niccolò Machiavelli was painted by Santi di Tito in the late 16th century and hangs in the Palazzo Vecchio. It shows a man in a black cloak with red sleeves and collar, resting one hand on a stone ledge and holding a book in the other.

Why it matters

Because no portrait was made of Machiavelli during his lifetime, this painting, created decades after his death, became the image most people associate with him. It reflects how later generations imagined the author of The Prince, shaping his legacy as much as his writings did.

Look closer

  • Why might an artist include a book in a portrait of a writer?
  • Since this was painted after Machiavelli died, how reliable do you think it is as a record of his actual appearance?
  • What might the dark background and formal pose be meant to suggest about the sitter?

This painting is part of the curated material that grounds the AI version of Niccolo Machiavelli on Humy.ai — when students ask about related events, the AI can quote it and cite it.

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Title page of the 1550 Italian edition of Machiavelli's Il Principe, with the title and subtitles in black letters on aged paper, a woodcut portrait bust of a man holding a book, two oval emblems, and the date MDL at the bottom.Book

Primary source

The Prince

Niccolò Machiavelli · 1513

Letter

Primary source

Letter to Francesco Vettori

Niccolò Machiavelli · 10 December 1513

Title page of an early printed book, 'Discorsi di Nicolo Machiavelli, Fiorentino, sopra la prima deca di Tito Livio', with a woodcut border showing a lion's head at top and a wolf standing on a ribbon inscribed 'DISSIMILIVM INFIDA SOCIETAS' below. Handwritten marks appear in the margins.Book

Primary source

Discourses on Livy

Niccolò Machiavelli · c. 1517, published 1531

Title page of a 1556 printed edition of Machiavelli's comedy Mandragola. Large capitals read MANDRAGOLA COMEDIA FACETISSIMA DI M. NICOLO MACHIAVELLI FIORENTINO, followed by Nuovamente corretta & Ristampata. A woodcut of a mandrake plant with roots and leaves is centered between the text. At the bottom reads IN FIORENZA MDLVI.Book

Primary source

The Mandrake

Niccolò Machiavelli · 1524

Photograph of a handwritten manuscript page on aged, yellowed paper, showing dense cursive Italian handwriting in brown ink, with a dedicatory opening line at the top. A small embossed seal or stamp appears at the bottom center, and a faint initial is written at the lower right.Book

Primary source

Florentine Histories

Niccolò Machiavelli · commissioned 1520, presented 1526, published 1532

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