Derek (Wilson Cleveland) gets slapped with a lawsuit and seeks help from attorney Josie Lanning (guest star Julie Warner). Jack loses his only client and most of his friends. Also guest starring Teri Reeves.

Derek (Wilson Cleveland) crumbles from personal and financial pressure after a chance encounter with his attorney Josie Lanning (guest star Julie Warner) and June Pepper (guest star Eliza Dushku) is there to help him pick up the pieces with an offer he can't refuse.

Jack has a plan to win the contest and save his friends' businesses. The problem? No one trusts him, no one likes him, and "friends" has become a very loose term.