How did Chicago develop one of the largest and most successful Bicycle Sharing Systems in a very short time, what benefits does this system afford to the city and its residents, and what developments threaten this success? Urban areas benefit significantly and in a variety of ways from micromobility, which contributes to an urgently needed sustainability transformation. In this qualitative, exploratory case study, we examine the foundations of the success and types of benefits of the second largest bicycle sharing system in North America, the City of Chicago’s Divvy. We juxtapose our data, which consists of participant and non-participant observations, fieldwork, interviews, documents, and social media posts, with a typology gleaned from the academic literature on bicycle sharing systems to explore Divvy’s wide-ranging positive impact. This typology includes economic, environmental, health and safety, and quality of life benefits. In addition, we identify two further benefits from our data: modularity and zoetic capacity. Despite this impact, we show how the consequences of changes in the ownership structure since 2018 are threatening the success and benefits. The emerging service model is no longer based on the initial pillars of its success: the city’s policy and vision for Divvy, the funding and ownership structure, and the strategic deployment of bicycle stations to balance demand potential with locational equity. Based on our study, we conclude that it is unlikely that the new micromobility system, refocused on more profitable e-bike and e-scooter rentals in privileged neighborhoods, is viable in the long term because it is abandoning the core values that embedded Divvy into the fabric of the city. Worse, the emergent model may actually contribute to a systematic exclusion of poorer neighborhoods and less privileged residents of Chicago.