As on-demand labor platforms proliferate the independent contractor business model, plaintiffs' attorneys in the United States have filed dozens of misclassification lawsuits to secure rights and protections for workers. The conventional wisdom is that if these lawsuits are won, then they will reverse the growth of insecure work. This Article challenges this widelyheld assumption. Using empirical research, I examine the trajectories and legacies of three celebrated misclassification lawsuits from earlier moments of transportation "gig work" in California: Tracy v. Yellow Cab Cooperative, Friendly Cab v. NLRB, and Alexander v. FedEx. Against many odds, plaintiff workers secured judicial recognition of employee status in each of these cases. The untold, post-litigation stories, however, were surprisingly grim: workers' economic lives were no more secure-and in some cases more precarious-then before the lawsuits. While I maintain that such litigation plays an important deterrence role, this Article highlights the significant limitations of misclassification litigation victories in effecting and enforcing the rights of gig workers. Based on this data, I critique the (over) reliance on the private enforcement of employee-status to fight precarity in the on-demand gig economy and suggest lessons for future advocacy.