Public officials are entrusted with hard-earned tax dollars meant to benefit the community in ways set out by elected representatives. Controls and policies are put into place to ensure that individuals do not misappropriate those funds for other purposes, including their own personal gain. Sometimes safeguards are insufficient or break down in the face of human failings and human relationships. This case, which is based on actual events, illustrates ways in which the principles of proper internal controls, good human resources practices, and effective ethical reasoning were all lacking. Background is provided about a city comptroller who rose from humble beginnings to earn the trust of his co-workers and community. He used his position to embezzle funds to finance an affair with a vendor to the city. The existing internal controls did not catch him, and his thievery was not discovered until he left the city’s employment.