Consequential historical decisions that shaped transportation systems and their influence on society have many valuable lessons. The decisions we learn from and choose to make going forward will play a key role in shaping the mobility landscape of the future. This is especially pertinent as artificial intelligence (AI) becomes more prevalent in the form of autonomous vehicles (AVs). Throughout urban history, there have been cyclical transport oppressions of previous-generation transportation methods to make way for novel transport methods. These cyclical oppressions (...) can be identified in the baroque and modernist periods, and a third oppression may occur in the contemporary period. To explore the idea of a third oppression, we focus on the bicycle and outline the history of cycling to understand how historical mode oppression unfolded. We then present several social and political factors that contributed to the oppression of cycling and share recommendations for how to avoid future oppressions including political, social, and design actions for researchers and policymakers to take. This paper argues that priorities for AI-enabled mobility and cyclist needs be advanced in proportion to the extent that they contribute to societal goals of urban containment, public realm, and proximal cities. Additionally, future mobility evolutions should prioritise mobility justice and mode choice over inducing a singular transportation method. (shrink)