This dissertation consists of three essays which examine topics at the intersection of law and finance. The first essay investigates the role of regulatory sanctions and reputational damage in financial markets. We study the impact of the announcement of enforcement of financial and securities regulation by the UK’s financial regulators on the market price of penalized firms. We find that reputational sanctions are very real: their stock price impact is on average almost 9 times larger than the financial penalties imposed. Furthermore, reputational losses are confined to misconduct that directly affects parties who trade with the firm (such as customers and investors). In the second essay we analyze the costs and benefits associated with se...