This essay examines the four pinnacles of the Man of Sorrows produced by the Vivarini workshop for polyptychs painted between 1440 and 1450, the Parenzo, Madonna, Praglia and Certosa Altarpieces. These panels of the Imago pietatis heralded by at least ten years or more Giovanni Bellini’s famed series of innovative interpretations of the same figure of c. 1455–1470. Unlike Bellini’s versions, those executed by Antonio Vivarini, his brother-in-law and younger brother (Giovanni d’Alemagna and Bartolomeo Vivarini) negotiated between a time-honored iconic serenity and the practical requirements of specific devotional cults. While complying with historic traditions, the Vivarini atelier nonetheless adapted to innovative pictorial solutions and aptly met the needs of individual altar dedications and exacting groups of patrons, among them Benedictine nuns in Venice, Benedictine brothers in Praglia and Carthusian monks in Bologna. By exploring the sponsorship and site of each commission, we can attempt to re-assess the art of Antonio and his collaborators. Most important, we avoid the pitfall of evaluating the early production of the workshop by wrongly examining it through the lens of later repetitions of the same subject produced by Bartolomeo and Alvise (Antonio’s son) during the 1460s, ’70s and ’80s.