Among the most distinguished figures in the history of European commerce is Simón Ruiz Envito, a merchant banker whose commercial and financial activities were carried out mainly within the framework of the great fairs of Medina del Campo. We have news about his life and professional achievements, his business relationships and his immense fortune thanks to the conservation of his extraordinary mercantile and family archive, a documentary collection considered one of the most important archives among the great businessmen of his time.This portrait responds to the courtly type that nobles and members of the upper bourgeoisie used throughout the 16th century, emulating the rigid and majestic image of the monarchy. The painting is not signed and it has traditionally been proposed that it was authored by the workshop of Juan Pantoja de la Cruz, a portraitist at the Court of Philip II, or some follower of his circle and continuation of his portrait work.