This case study is based on the epic divestment of Air India which eventually did not take off. Post ill-conceived merger without any synergies, the losses began to enlarge exponentially. This led the carrier to financial losses, apart from that enormous order of 110 fleets without having the capacity to pay, crippled the financial status of the airline substantially. All the government’s effort to restructure and turn around the airline proved to be a failure. The plot for this case is set as, considering the government’s inability to cope with its debts and meet day-to-day expenses in this extremely competitive industry, the Union Cabinet gave its ‘in-principle’ nod to divest holdings in Air India, but had not formally announced for the bidding process, a group of ministers are still working on terms of divestment. Meanwhile the news created a buzz and potential bidders have started informally expressing their interest in Air India. The government is expecting more and more bidders to participate to derive maximum out of the auction. When more and more bidders participate in a bid, the bid amount always ascends and a situation of winner’s curse is created where the winning bidder has a feeling of regret by over-paying the amount in order to win the bid. The subject that this case will fit into is Game Theory and Strategic Management courses and central theme or concept to be taught through this case is situation of winner’s curse and some more concepts related to Auctions and Strategy.