The Hebrew word “maskil” often describes a prudent person in general, while many of the Dead Sea Scrolls suggest that it designates a particular sage. The majority of scholars have argued that the figure of maskil was a leader of the sectarian movement (recently esp. Carol A. Newsom and Judith H. Newman), yet it has also been demonstrated that the term can simply mean “insight” or serve as the adjective “wise” (Robert Hawley). At the very minimum, maskil stands for a wise figure of some kind, as is indicated by the rule, wisdom, and liturgical texts that associate him with specific tasks and portray him as a first person speaker. This paper explores the character of maskil beyond the understanding of those Jews who used and collected the Qumran corpus. Leaving aside the debate about his position in the Qumran sectarian movement, the diverse maskil materials are examined in order to understand how the role of this figure is imagined and idealized in the ancient documents from the Qumran caves. The way in which wisdom is embodied in the maskil’s portrayal will deserve special attention. In other words, what kinds of concrete exercises maskil undertakes in order to attain, perform, and/or retain his wisdom according to the extant sources? Following a survey of the Dead Sea Scrolls, the portrait of maskil is compared with descriptions of other sages from the Hellenistic and early Roman periods, particularly those depicted in Qoheleth, Ben Sira, Wisdom of Solomon, and Philo of Alexandria’s texts. It will be argued that the maskil accounts of the Qumran collection reflect wider early Jewish discussion, which took place in the eastern Mediterranean context and concerned the nature of a life dedicated to wisdom. In particular, it is characteristic of several works to attribute sets of exercises to sages in order to highlight the lived aspect of the wisdom tradition.