The principal goal in calculating damages is to make the injured party whole. This exercise often is simple in theory but can be excruciatingly complicated in practice. In most cases, courts are presented with competing experts offering damage valuations based on estimates, forecasts, projections and discounts, and are then tasked with rending this information into a monetary amount sufficient to compensate a party for its injury. As a result, a damage award may be more of a "best guess" than a mathematically precise reflection of the harm caused by the liable party.

In Maverick Therapeutics v. Harpoon Therapeutics, C.A. No. 2019-0002-SG (Del. Ch. April 23, 2021), the Delaware Court of Chancery considered the appropriate measure of damages for fraudulent misrepresentations made in connection with investments in a cancer therapeutics company. Given that the technology involved was cutting-edge but unproven (at present, but more importantly as of the historic date of the fraud), the court was challenged to determine the value of the defrauded party's investment. To deal with this challenge, the court employed a useful analogy: that the defrauded party's investment in a novel, nascent treatment was akin "to the purchase of a lottery ticket, a risky investment with a low probability of a large pay-out." Applying this analogy, the court reasoned that the defrauded party's damages could be calculated as the difference between two lottery tickets—the ticket the defrauded party thought it had purchased, and the ticket it actually received as a result of the fraud.