The authors respond to a proposal in this issue of Academic Medicine by Ray, Bishop, and Dow, who recommend adopting a free-market approach to the Match in which applicants and programs negotiate directly with each other to find and fill residency positions year-round. This Invited Commentary examines and responds to the reasons Ray and colleagues give for changing the Match and explores their proposal's implications and likelihood of success.The authors question Ray and colleagues' argument that assumptions underlying the National Resident Matching Program algorithm have been violated. The authors suggest there is insufficient evidence for the "July effect" and that the possibility for improvement in physician supply due to the year-round entry of graduates into the workforce ultimately faces the rate-limiting step of caps on residency positions allocated to programs. Most important, competency-based medical education, on which the free-market proposal depends, is not yet sufficiently developed.Nonetheless, the imbalanced ratio of applicants to positions in the Match is contributing to a rise in the numbers of student applications and program interviews. Although the proposed free-market approach might, as Ray and colleagues envision, curtail applications as well as reduce time and financial resources currently expended on the process, it would require significant changes on the part of applicants, residency programs, medical schools, and other stakeholders.Because the proposed free-market approach could reduce some negative effects of the imbalance of applicants and positions, it merits ongoing discussion along with other more immediate practical solutions to issues with the Match.