In a special three-hour episode, the teams take on two tasks, and two Celebrities are fired. It all begins when Mr. Trump tasks the teams with creating and selling a Celebrity guidebook on New York City. With a big bonus on the line, special guest Regis Philbin judges the teams' books. Despite the added incentive, one Project Manager neglects the quality of their book, while the other team struggles just to get theirs completed in time. An explosive boardroom leads to another Celebrity being fired. The evening continues, as the teams create an interactive health segment for Walgreens. Before the Celebrities can even begin their task, Mr. Trump switches up the teams. One Project Manager struggles to maintain control of an insubordinate teammate, while the other team tries to complete the task with a Celebrity missing. Before anyone is even fired, Mr. Trump witnesses one of the season's biggest Boardroom battles, resulting in one Celebrity going AWOL.

This week, the teams must create their own puppets and perform in front of a live audience for Henson Alternative's "Stuffed and Unstrung" improv show. One outspoken Celebrity struggles to be a team player. On the other team, another Celebrity fights for a role in the task, but is marginalized and has a breakdown. Both teams put their improvisational skills to the test, but only one is declared the winner and another Celebrity hears Donald Trump's dreaded words, "You're fired!"