The Byzantine Empire experienced the 14th century, especially the second part of it, as a period of economic decadence because of devastating civil wars and numerous invasions. As the financial difficulties of the century widened the gap between the rich and the poor, the resulting social stratification eventually made inequalities more apparent. The intellectuals of the century who tackled these current problems not only condemned greed as evil and unjust, but also encouraged the rich not to be avaricious and to be more generous toward the poor. The rich were regarded as people who abuse the possessions that God bestowed on all humankind, including the poor. In this context, the practice of moneylending constitutes a ground where these two conflicting groups interacted, and the “creditor”, as a component of wealthy people, played an important role in the monetized Byzantine economy in which people borrowed and lent money for various reasons. While the economic and political instability created an atmosphere of insecurity within Byzantine society, the value of credit dramatically increased. Yet the creditors were subject to a mood of distrust, and they became harsher in order to satisfy their loans, as more and more people were in greater need of cash but unable to repay their loans under the worsening conditions of the empire. These circumstances can be observed in the increasing number of cases concerning credit transactions that were brought before the patriarchal synod in Constantinople, especially at the end of the century. This paper aims to analyze the concepts of “generosity” and “avarice” by focusing on the relations between the creditor and the debtor as reflected in the jurisdictional decisions of the patriarchal court in 14th-century Constantinople.