In recent years, voluntary health insurance costs have become a major source of friction in labor-management negotiations. What was once a “fringe” has led to job actions, strikes, and intensive bargaining. We examine the history of labor's participation in New York Blue Cross from the 1930s to the recent past and show that labor's participation in the plan was crucial to Blue Cross's success in the plan's early decades. By the late 1950s, serious tensions developed over rate increases and the participation of labor in Blue Cross governance. Ultimately, the issue was one of the control over what was provided by the plans and who would pay for the costs of care. We posit that labor was never able to achieve an important role in the control of the third-party payer, and in the antilabor environment of the 1980s this proved detrimental to labor's interests.