Shams al-Dīn Muḥammad Malikdād Tabrīzī (d. ca. 646/1248), better known as Shams-i Tabrīzī, was an enigmatic and vagabond Sufi and is renowned for being the spiritual guru of the most celebrated Persian Sufi poet, Jalāl al-Din Rūmī (d. 672/1273). In the centuries following the passing of Rūmī, hagiographers of the Mevlevi Sufi Order often described Shams-i Tabrīzī as an unconventional and transgressive qalandar whose demeanors were at odds with the normative Sufi practices of his day. Such depictions even led to the creation of an offshoot Sufi order called Shams-i Tabrīzīs in 16th century who were openly practicing antinomianism. Scholars such as Abdulbaqi Gulpinarli, Ahmet Karamustafa and Franklin Lewis discussed the legacy of Sham-i Tabrīzī in the works of post-Rūmī authors in Anatolia. Yet there have been few studies about the mythical depiction of Shams-i Tabrīzī in the works of hagiographers and its potential relationship and contribution to the development of some of the antinomian ideas and practices within the pre-16th century Mevelvi Sufi Order. This paper aims to evaluate the aftereffect of Sham-i Tabrīzī’s mythical legacy in hagiographies such as Manāqib al-ʿārifīn of Sham al-Dīn Aḥmad Aflākī (d. 761/1360) and its impact on the perpetuation and dissemination of some of the heterodox motifs, metaphors, and narratives in the works of early Mevlevi Sufis. The main argument is that in the hagiographical tradition, Shams-Tabrīzī— as the most prominent spiritual master of Rūmī— was often depicted in particular way to fit the antinomian practices that were becoming rampant, among the Sufis of all stripes including the Mevlevis in the post-13th century Anatolia. In the process, I also hope to offer a new approach in further understanding of the overall mystical milieu of 14th to 16th century Anatolia in which some of the direct descendants of Rūmī adopted openly transgressive behaviors which they presumed were in line with Sham-i Tabrīzī’s style of antinomianism.