Caravaggio’s early production as a portrait painter is still the subject of research and a fount of enigmas. Despite the numerous citations in documents, only rarely have these been linked unequivocally to paintings known to date. This is also the case with the ‘portrait of Farinaccio criminalist painted on a head-size canvas believed to be by Michelangelo from Caravaggio’, that was listed in the 1638 inventory of the Marquis Giustiniani and with ‘the speaker wearing a robe, painted by Caravaggio’ on a head-size canvas, owned in 1652 by Caterina Campani, Onorio Longhi’s wife.

The present multidisciplinary research examines the rediscovery of the portrait of Prospero Farinacci by Caravaggio. The painting, undisclosed until now, hides an underlying female portrait. The authors investigate both compositions from a technical, iconographical and critical point of view, supporting Caravaggio’s attribution. The technical researches allow cross-validation in the brushwork and materials of the picture, compared to Caravaggio’s early painting technique and style. The portrait of Maffeo Barberini, recently re-ascribed to Caravaggio, shows a significant similarity, while the underlying woman of the retrieved painting closely resembles the gipsy of the Louvre Fortune teller. In addition a newly introduced and advanced imaging technique (Ma-XRF) has detected on the male portrait the feature of the lawyer’s robe, which supports the identification with Prospero Farinacci.

The intriguing topic of physiognomic accuracy versus stylizing tendency in Caravaggio’s portraiture is considered with the aid of Giulio Mancini’s observations.

Besides, the possible interpretation of the underlying figure as a religious subject sheds a light on the obscure activity of the young Caravaggio in Lorenzo Carli’s workshop, recently brought to scholars’ attention by new documents and hypotheses.