Nabati poetry, or the oral vernacular poetry of the Arabian Peninsula, is no longer an art form practiced solely by desert Bedouins. It has been taken up by rulers of the Arabian Gulf states who as poet-princes place themselves within a poetic tradition that is centuries old. As active composers and performers, they expand upon the historical role of Arab rulers as patrons of poetry. The present paper investigates how Shaykh Muhammad bin Rashid Al Maktoum, ruler of Dubai, employs nabati poetry for the purposes of strategic self-representation and legitimation. Specifically, it sheds light on Al Maktoum's literary riddles as a heavily patronized body of literature. A close reading of selected riddles devotes attention to those rhetorical strategies that function to negotiate the respective positions of this poet-prince and his subjects and poetic peers. The analytical focus is twofold. First, building on existing scholarship on the patronage of poetry in the Arabic literary tradition, I shed light on the complex power relations at play in the riddle competitions. Secondly, the work of Pierre Bourdieu and George Herbert Mead forms the theoretical backdrop for a discussion of Al Maktoum's socio-political persona as constructed through his poetry.