25 June 1599
Contract for the Contarelli Chapel
A contract was signed to decorate the Contarelli family chapel in San Luigi dei Francesi with canvases of scenes from the life of Saint Matthew, for 400 scudi. The commission was presumably arranged through Cardinal del Monte.
28 November 1600
Beats a cardinal's guest with a club
While living at the Palazzo Madama with Cardinal del Monte, Caravaggio beat the cardinal's guest, the nobleman Girolamo Stampa da Montepulciano, with a club, prompting an official complaint to the police. Brawls and arrests, with spells in the Tor di Nona jail, grew ever more frequent.
1601
A studio of his own, and pupils
Caravaggio rented a studio of his own, where his celebrated pupils Bartolomeo Manfredi, Mario de' Fiori and Leonello Spada painted their pictures.
1602
Cecco, model and companion
The model for “Amor Vincit Omnia”, painted in 1602 for Vincenzo Giustiniani, was 'Cecco' — possibly Francesco Boneri, later known as the painter Cecco del Caravaggio. He lived with Caravaggio in Rome and stayed with him even after the flight of 1606; the two may have been lovers.
14 June 1602
Commission for “The Death of the Virgin”
He received the commission for a painting for Santa Maria della Scala in Trastevere; the model for the Virgin is said to have been a prostitute drowned in the Tiber, or else the artist's mistress. Other accounts date the commission to 1601.