The Art Dealer's Apprentice tells the story of how the author moved to New York in 1989 as a young Midwesterner, found a job at an Upper East Side gallery, and became the protégé of Carla Panicali, an Italian countess and major international art world figure. From Carla - an extraordinary woman whom he deeply admired - the author learned to navigate the treacherous waters of authenticity, power and money in the art business and his own life. As gallery director, he gradually piloted the gallery through a sea of fakes, frauds, and unscrupulous colleagues, competitors, collectors and experts, until the art market crashed, and in the ensuing crisis, in the increasingly money-driven art world of the 1990s, he came to question even the authenticity of his friendship with Carla.

In The Art Dealer's Apprentice, the author recounts how he learned the New York art business from the inside, including the roles of dealers, auction houses, runners, collectors and experts; the personal histories of famous artists and the art historical importance and salability of their work; and how paintings and sculptures were (or were not) authenticated and sold, often based, surprisingly, on factors having little to do with the artwork itself. The author also details how international business was done, in some cases through illicit transport of artworks, payoffs to experts, and Swiss bank accounts. Increasingly disillusioned, the author ultimately concludes that by the early 1990s, the art business was no longer really about art.