This paper seeks to explore the various interconnected theological aspects present in the Eastern Orthodox phenomenon known as the holy fool by bridging 2 notions; feigned madness and salvation. It will begin by addressing the inception, and scriptural origin of holy foolery. Moving from presenting the definitions and ideologies from a rather widespread perspective, this research will come to focus on the holy fools of Russia, attempting to address the factors which have contributed to the strength and duration of the presence of holy fools in Russia over the centuries; far outlasting that of other Eastern Churches, and impacting its theological, socio-cultural, and literary history. In analyzing this phenomenon particularly within the Russian context, it is essential to address notions of Russian mysticism and several central ideologies of theologian Vladimir Lossky. Within this discussion, the concepts of salvation and deification will emerge. Ultimately, the goal will be to assess the ways and reasons for the unicity and duration of the holy fools’ existence in Russia and to convey the deeply rooted connection between this practice and the Eastern Orthodox understanding of theōsis as salvation.