The man holds incredible power in the courts of 16th century Rome and over many important figures of the time. He wrote Il Libro del Cortegiano (The Book of the Courtier), which served as a pivotal took for modern historians in understanding the Renaissance. The book describes what a true gentleman should be including moral, intellectual and physical attributes - basically a how-to bro guide. Although "bro" back then used to be some stature to attain, not one to degrade yourself to. The point that comes most across in Raphael’s 1514 genuine portrayal of Castiglione is the fact that a courtier should not have to show he is one, the simplicity is what shows everyone how much of a man he really is.

When observing his portrait, Castiglione seems to change his expression before your eyes. His eyes are neither raised nor lowered as he views you as an equal. Never known to raise his voice, or strike an unfair bargain, Castiglione was one of the most sophisticated minds of his time. The portrait does not suggest that he is a genius for the palette and reserved position offer a more unpretentious look at the man. The diplomat meditates between the two extremes of black and white with his gray ensemble, as he weighs multiple view points without coming to any hasty decisions.