The former Mayor of New York is a constant critic of the current administration, and a plan to appease him has tragic consequences. Meanwhile, Michael and Ashley try to avoid their annoying new neighbors. And Nikki holds a contest among the men in the office to prove that none of them could ever be fathers.

When Mayor Winston's nominee for the Public Schools Chancellor proves an embarrassment to the administration, James urges Mike to stick with the controversial candidate. In the meantime, Ashley considers a career in television on a roundtable show.

An opinionated school janitor becomes ""Mayor for a Day"" when he wins an essay contest intended for schoolchildren. Meanwhile, the Mayor wants to change his image.

For the Mayor's 50th birthday, Paul is determined to get his ""old friend"" George Stephanopoulos to attend the event; as Michael arranges for birthday wishes from David Letterman, Patrick Ewing, Al Michaels, Dan Dierdorf, Frank Gifford, Rosie O'Donnell, Larry King, and the cast of Rent. But in the midst of the planning, a scandal swirls about the Mayor's presumed affair with a staffer from the Governor's office.

Michael discovers that his new girlfriend, Gayley, is paying for law school by moonlighting as a stripper. Meantime, Claudia catches Paul in a lie, and Nikki plays mind games with Stuart.

Despondent over his separation with his wife, the Mayor decides on a whim to take a road trip with Paul, leaving Mike in charge of New York City and scrambling to find out where they went.

Mike struggles to make the children of New York believe again after the Mayor tells them that there is no Santa.

Stacey's grandmother puts a curse on Mike after he convinces her to move out, into Manhattan. The Mayor is concerned he's losing his hearing. And there's a void in Stuart's life after he is moved upstairs and is not allowed to make sarcastic comments anymore.

Stuart lobbies to become Carter's roommate. After Carter's apartment is robbed, he must let Stuart stay. A rat on the loose in City Hall wreaks havoc on the staff and Paul's cat.