This paper addresses the question the Ottoman rise narrative from the point of view of architectural history. In this narrative, the monuments designed by chief architect Sinan (d. 1588) are presented as the culmination of Ottoman architecture in the ‘classical age’. Sinan is presented as an early modern star architect in the empire’s service, building peerless monuments after which only decline could follow. Two consequences emerge from such approaches. First, Ottoman architecture built after Sinan’s death becomes part of a decline narrative, with the result that the seventeenth century remains the least studied period of Ottoman architectural history. Second, and more relevant in the present context, Ottoman monuments built between the early fourteenth and the early sixteenth century are integrated into a narrative leading towards Sinan’s projects. Effectively, both the rise and decline paradigms are embodied in a framework that centers Sinan’s buildings as masterpieces. Stepping way from this narrative, recent scholarship on Ottoman architecture in the fourteenth and fifteenth century has shown the diverse nature of construction projects in this period. Elements of Byzantine, Seljuk, Timurid, and Mamluk architecture were integrated as workers with various backgrounds and expertise are active on construction sites under Ottoman patronage. Such diverse construction projects continued in the period of crisis after Bayezid I’s defeat at the hands of Timur, and beyond as territories lost in 1401 were slowly regained, and expansion continued. With the Ottoman conquest in 1453, the creation of a new capital began, with imperial construction projects under Mehmed II focusing on Istanbul. While imperial Byzantine architecture, and particularly Hagia Sophia, increasingly served as model and inspiration, Ottoman builders remained engaged in a wide range of building practices. Not until the late fifteenth and early sixteenth centuries did increasing centralization of artistic production lead to the emergence of an easily recognizable style that would become closely associated with Ottoman imperial rule. A few decades later, Sinan’s work built on these earlier designs. This paper draws a long arch from the early fourteenth to the mid-sixteenth century, arguing that stepping away from a narrative predicated on Ottoman rise, we gain new understandings of the empire’s complex architectural heritage.