Dispatched in 1502 by the Florentine Republic to watch the operations of Cesare at Imola, with secret instructions to offer the Duke false promises in the hope of eliciting information that could be relied upon, Machiavelli had enjoyed the rare pleasure of a game at political ecarte with the subtlest and most unscrupulous diplomatist of his age.

He had witnessed his terrible yet beneficial administration of Romagna.

He had been present at his murder of the chiefs of the Orsini faction at Sinigaglia.

Cesare had confided to him, or had pretended to confide, his schemes of personal ambition, as well as the motives and the measures of his secret policy.

On the day of the election of Pope Julius II.