Past research on idiosyncratic deals (i-deals or individualized employment arrangements between some employees and their employers) provides evidence that these arrangements are beneficial for individuals who secure them (“i-dealers”) and the employers that grant them. While this body of work has been instrumental in showcasing the value of i-deals to organizations, I contend that it provides a simplistic picture. Most research has focused on the outcomes of i-deals for the parties involved but has not deliberated on if, why, and how the i-dealer and employer perceptions of i-deals (and resultant outcomes) may change over time as the i-deal unfolds. I argue that one cannot assume that once granted, an i-deal will hold the initial value it had at the time of negotiation for the i-dealer and/or the employer. In this work I develop a processual explanation of how over time, it is the mechanism of i-deal value assessment by the i-dealer and the employer that drives i-deals into different pathways or trajectories. In doing so, this work presents a theoretically grounded framework that chisels out drivers at different levels that can alter the value of i-deals for the i-dealer and the employer. Due to change in value, the two parties will reappraise the arrangement which will impact the trajectory of the i-deal (depending on the changes (or no change) in its value for the i-dealer and/or the employer). I discuss i-deal maintenance and other possible i-deal trajectories that may emerge e.g., i-deal transformation into we-deal or a Human Resource (HR) practice, i-deal renegotiation/new i-deal for the i-dealer as well as ultimate i-deal termination. I also deliberate on the practical and research implications of this work.