New York attorney Carl Sack joins the Boston branch of Crane, Poole & Schmidt, ruffling feathers amongst the staff, including Denny who is arrested for soliciting a prostitute, and Clarence who is targeted for performing in a drag show.

Meanwhile, Alan defends Shirley when she is sued for withdrawing a large contribution to an academic study, but is distracted by the familiar opposing council. Jerry helps freshman lawyer Katie Lloyd try her first case involving a murder suspect who refuses to cooperate.