Liz and Jenna’s friend, Claire Harper, a free-spirited stalker-type, shows up unexpectedly in New York to visit. But once she gets there, she centers her attention on Jack and claims him as her own. Tracy, trying to cheer up Kenneth because of the new page uniforms, invites the cast of Night Court to visit.

Liz, on a return trip from Chicago to get out of jury duty, ends up sitting next to Oprah Winfrey and spills her soul to her for advice. Meanwhile, Tracy and Jenna argue as they attempt to figure out whose life is harder, leading to a wacky "social experiment". Kenneth tests Jack’s morality after an Olympics snafu.

When Don decides to promote Jack and make him his successor over Devon, Jack decides to give his old job to Liz because she always has his back. However, a turn of events concerning Don’s health compromises Jack’s promotion. Meanwhile, Tracy thinks that his son is embarrassed of his career because he did not invite him to fathers day at school.

Dennis becomes a New York City celebrity after jumping in front of a train and saving someone who fell on the tracks. Meanwhile, Jack desperately tries to persuade Tracy to become the celebrity face of the Republican Party.