For long, migration and diaspora have been perceived negatively, resulted from social and psychological turmoil. They are believed to produce devastating outcomes, as the loss of identity, cultural hybridity, psychological crises, and social instability. Theorists, as Homi Bhabha, believe that "unhomliness", having lost the feeling of possessing a home, may also result in migration and cultural diaspora, as Robin Cohen argues. Yet, it is an illegitimate overgeneralization. I tend to propose a new perspective in this regard. I believe that specific types of diasporas have come to collaborate hugely in the progress of individuals epistemologically, psychologically, socially, and intellectually. I have drawn a comparison between the falsely undisputed notions of home, migration, diaspora, hybridity, and "unhomeliness" on one side, and on the other side this "Wandering Jew" phenomenon, which I have proposed. Moreover, this title has been deliberately adopted to refer to the negatively perceived notion of the myth of the Wandering Jew, that he is the everlasting sufferer. Contrarily, he might be the wisest, the ultimate 'uncaged', free living individual. This notion will be applied on V. S. Naipaul's The Enigma of Arrival, which aptly fits into this proposed phenomenon.