Caravaggio left Arpino's workshop in January 1594 and began selling works through the dealer Costantino, with the assistance of Prospero Orsi, an established painter of Mannerist grotesques (masks, monsters, etc.).

The second boy, a cardsharp, has extra cards tucked in his belt behind his back, out of sight of the mark but not the viewer, and a sinister older man is peering over the dupe's shoulder and signaling to his young accomplice.

The subjects of The Fortune Teller and Cardsharps offered something new: realistic scenes of street life, especially with this beautifully rendered attention to little details such as the split fingers on the older man's gloves, or the teenage cheat's anxious glance at his master.

The Cardsharps, with its mixture of brutal low-life realism and luminous Venetian delicacy, was much admired, and Orsi "went around acclaiming (Caravaggio's) new style and heightening the reputation of his work."

Whether through Costantino or Orsi, Caravaggio came to the notice of the prominent collector Cardinal Francesco Del Monte, who purchased Cardsharps and became the artist's first important patron, giving him lodgings in his Palazzo Madama behind the Piazza Navona,[2] then as now one of the principal squares in Rome.