In 1957, the courtrooms in India witnessed a high-stakes legal battle. It was fought in two innings, first in the Bombay High Court and later in the Supreme Court of India. The Supreme Court’s verdict in R. M. D. Chamarbaugwalla vs. Union of India outlined core principles to determine if any economic activity constituted gambling. Even after 69 long years, the doctrines applied to interpret the Constitution inform our understanding on matters pertaining to gambling and betting. In the light of the recent ban on online real money games by the Union Government, this oft-forgotten legal dispute demands a fresh glance from anyone interested in public policy. One of the brightest advocates in independent India represented the parties involved in this legal conflict. Nani Palkhivala represented R. M. D. Chamarbaugwalla, the founder and Managing Director of R. M. D. C. (Mysore) Limited against the State of Bombay and later against the Union of India.