2I am thankful to my main advisor professor Steven Matthews for very detailed feedback and patient support. I am grateful to my dissertation committee members professor George Mailath and Nicola Persico for incisive comments. I also thank Jing Li, and Ichiro Obara, and audiences at the Economic Theory workshop at University of Pennsylvania. All errors are my own responsibility. This paper studies a principal-supervisor-agent model in which a privately informed supervisor is susceptible to collusion. We model collusion as a side mechanism pro-posed by the supervisor who observes a private signal correlated with the agent’s type. We explore how the supervisory information helps the principal to extract informa-tion rent from the agent when th...