$100 million. That is what Ivan Boesky paid the United States as part of a negotiated settlement to charges of inside trading. The Boesky and related securities fraud scandals focused unprecedented attention on the corporate restructuring phenomenon in general and risk arbitrage in particular. Much of the considerable public unease over the scope of corporate restructuring focused on the role risk arbitragers play in fueling the market for corporate control. Risk arbitragers also played some role in triggering the stock market break of October 19, 1987. This article explores the debate over risk arbitrage spawned by the Boesky scandal and the October 19th event. The debate primarily concerns the proper role federal securities law should play in regulating risk arbitrage.