Although the Host demands a merry tale from the Monk, the Monk instead gives a series of cameo tragedies, all of which deal with the role of fortune in a man's life. The Monk catalogues the fickleness of Fortune through a series of abbreviated tales about such people as Lucifer, Adam, Hercules, Samson, Nero, and so on — all who were initially favored but eventually abandoned by Fortune. The Monk concludes when the Knight interrupts him and pleads for a merry tale.
The Monk's series of little tragedies report the gloomy news that all wealth and position in the world are pure illusion, and nothing can prevent the fall of the proud. The Monk sums up his theme in the introductory stanza: "For sure it is, if fortune decides to flee, / No man may stay her course or keep his hold; / Let no one trust a blind prosperity." ("For certein, whan that Fortune list to flee, / Ther may no man the cours of hire withhholde. / Lat no man truste on blynd prosperitee . . . .")
Why Chaucer wrote these stories for the Monk is unclear. They are monotonous, and the inevitable moral of each — one cannot depend on fickle fortune — comes as no surprise to the reader. This tale is often thought to be one of Chaucer's early writings. Certainly it has none of the subtly of most of his other tales. Some authorities believe that Chaucer at one time considered writing a book of tragedies, and since he never completed his book of tragedies, this perhaps accounts for the their inclusion in The Canterbury Tales. They were simply available and seemed suitable for the Monk to relate.
"now called Damascus" the suggestion is that Damascus now stands where Eden once was.
The Warning the moral "Don't tell your wife any secrets" differs significantly from the usual references to fortune in the other tragedies.
Centaurs, Cerberus, Busiris, Achelous, Cacus, and Antacus all part of the Labors of Hercules.
Trophee a prophet of the Chaldee.
Nessus a centaur slain by Hercules.
Odenatus the ruler of Palmyra.
Shapur king of Persia.
Aurelian (Aurelianus) emperor of Rome, preceded by Gallienus.
King Peter of Spain; King Peter of Cyprus; Bernabo Visconti of Lombardy; Count Ugolino of Pisa figures who relied on fortune and were betrayed, killed, or starved.
Alexander the representative of the ideal for the medieval person.
Brutus Cassius Chaucer erroneously supposes these two famous assassins of Julius Caesar to be one person, not two.
Croesus the king of Lydia who depended too strongly upon fortune.