This is Tschu the Allel, a character from my Autumn of the Empire of the Thousand Petal Throne setting for Evan Rowland and Hannah Shaffer’s upcoming roleplaying game Noirlandia.
In case you haven’t guessed (bless your hypothetical heart), the painting is not actually mine. It’s my manipulation of a painting by Agnolo di Cosimo il Bronzino. The original depicts Piero De Medici Il Gottoso (which is a pretty lousy sobriquet — it means “the gouty”).
The Empire of the Thousand Petal Throne is more top-down than Renaissance Italy, but with its backstabby, personal politics, it feels more like the constant low-level conflict of the Italian city states than a functioning empire.