In the premiere episode, Donald Trump challenges the 16 new Celebrities to run authentic New York City pizzerias to raise money for charity. One team uses their celebrity power on the streets of Manhattan, while the other races against the clock to complete a special delivery that could be the difference between winning and losing. Friends with deep pockets show up and pack both pizzerias, and the Celebrities set a fundraising record. But the excitement is short lived, as one Celebrity becomes the first to hear Donald's dreaded words: "You're Fired!" Ivanka Trump and Donald Trump, Jr.

In the third episode of the season, each team is given two Camping World RVs to stage an 'experience' in mid-town Manhattan. One Celebrity wrestles control away from their project manager. The other team questions the sanity of their leader, who stops working on the task to play a game of catch. It's a race to the finish, but one team ultimately stands victorious. The losing team faces Donald Trump in the boardroom where another Celebrity is fired.