What could be sweeter than the perfect portrait of a mother and child like Cosimo's Eleanora di Toledo with Her Son Giovanni de' Medici?

Generally, almost nothing. In the case of Eleonora and her son, however, just about anything up to and including a portrait of an actual corpse could be sweeter. Instead of Virgin and Child glimmering with hope, bathed in the golden rays of heaven, we have a halo of deep blue that radiates out from behind Eleonora, just reaching her son, Giovanni, the heir to the Medici dynasty. In this portrait, the gold is real, and Eleonora is covered in it.

This, the first portrait of the ruler’s heir, was a declaration to the world that the security of the future of Florence was safely in the hands of their dead-eyed offspring. This braggardly vehicle of propaganda meant to reassure the masses that all was well in the hands of the Medici ultimately fell short in the prediction department. Both Giovanni and his mother, Eleonora, would die from malaria in 1562.

The gold, jewels, and pearls that adorn the Duchess, and to a much lesser extent, Giovanni, speak not of the promise of a heavenly afterlife, but of the Medici’s riches of the moment. As much statecraft as a statement of grandiloquence, the cold effect of those portrayed along with Eleonora’s perfectly dismissive half-smirk intentionally establishes a sense of “royal distance” between itself and anyone lucky enough to gaze adoringly at it. If we are to believe what we see, life as a Medici was a flawless state of being.

Somewhere in this painting is a lesson about how looks can be deceiving, how a tiny parasite can derail a dynasty and change the course of history, and how the shining face of youth is no guarantee of future success.