Domenico di Bartolo for his work as a "gharzone di bottega". The term gharzone may define someone's position ranging from a full-fledged apprentice to a mere helper or worker. If the document indeed were to refer to Domenico, he was most likely at the beginning stages of his artistic training, and only eight years later in 1428 he finally made a standing for himself by being acknowledged in the painter's guild. On the basis of this payment document in 1420, it is most probable that Domenico was born sometime between 1400 and 1405. However, more accurate sources that record his exact date of birth have yet to be discovered today.
Carl Brendon Strehlke further elaborates that the payment documents for the Opera del Duomo show that, at the time, the Opera was overseeing several important sculptural commissions: a new pulpit for the Council of Siena, the decoration of the Cathedral pavement, and most importantly the construction of a new Baptismal Font. It is recorded that some of the most progressive artists in all of Tuscany were involved in these projects, names which include Ghiberti, Donatello, Francesco di Valdambrino, Domenico di Niccolo' de Cori, and Jacopo della Quercia. It is therefore not a surprise that Domenico's first extant painting, the Madonna of Humility of 1433, possessed strong sculptural qualities. Art historians such as Strehlke and Bruce Cole claim that it is highly likely that during the time that Domenico worked as a Gharzone for the Opera's projects, he received many influences from many of the mentioned sculptors. Other contemporary artists that existed during Domenico di Bartolo's time were Stefano di Giovanni and Giovanni di Paolo, who were already active master painters by their early twenties. Both di Giovanni and Giovanni di Paolo placed emphasis on more of the linear and emotive qualities of drawing, whereas di Bartolo conceived of forms in rounded masses.

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