The relationship between Dudley Carleton, the supposed 'connoisseur', and Rubens reveals neither in a wholly flattering light. Carleton misrepresented himself as a devotee of antique sculpture, whilst Rubens behaved high-handedly over an exchange of pictures negotiated by Carleton. When Carleton accidentally first established contact with Rubens in 1616, buying a 'hunting piece', this was organized by George Gage and Toby Matthew, the experts in the art market to whom Carleton subsequently left the trading of his unwanted sculptures for Rubens's paintings. Carleton did not genuinely appreciate the artist's pictures, since these were immediately offered for sale. Carleton was principally anxious to acquire paintings cheaply - for example, by Snyders, Vrancx and Brueghel obtained through Rubens's agency in 1617 - primarily as gifts for his patrons, with an eye on promotion. This article reassesses these episodes and suggests that aspects of connoisseurship at the early Stuart court are due for review.