Executive Summary: March Madness, the NCAA Division 1 college basketball tournament, is rapidly approaching. Second in betting popularity only to the Super Bowl, some have predicted as much as $3 billion will be bet on workplace bracket pools during March Madness this year. March Madness, Super Bowl, and Fantasy Football pools have become ingrained in the American workplace and seem harmless to many; however, permitting such activities creates a wide range of risks for employers, from productivity loss to discrimination and disability issues and even criminal penalties. Online gambling can also create headaches for employers and IT departments. Before turning a blind eye or participating in the pool, here are a few risks with which employers should become familiar.