Rideshare workers who drive for companies such as Uber and Lyft experience tensions in their occupational identity. These tensions are a result of rideshare drivers being denied the benefits and security of employee status (such as healthcare or unemployment) while also being denied the freedoms of independent contractor status (such as the ability to set their own labor rates). These tensions were especially prevalent in California during the November 2020 election because Proposition 22 was an initiative to determine whether rideshare drivers would be legally classified as employees or independent contractors. Although some rideshare drivers ruthlessly defended their right to be independent contractors and urged voters to vote “yes” on Proposition 22, others considered employee classification a route to better working conditions, higher pay, benefits, and much needed legal protections. In this case study, I utilized a qualitative content analysis of rideshare forums on a counterinsitutional website to showcase a) how trolling behaviors were pervasive in rideshare online discourse; b) how trolling impacted sensemaking about the rideshare professional identity; c) how trolling paradoxically united while divided rideshare drivers; and d) how drivers exercised control over one another. The study found that trolling was used by drivers to make sense of their occupational identity and create in- and out-groups on the platform. Additionally, downward social comparisons in intergroup interactions were used as a control mechanism amongst drivers. Implications and future directions are also discussed.