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1-50 of 149
- Mike Flaherty, the Deputy Mayor of New York City, and his team of half-wits must constantly save the Mayor from embarrassment and the media. Mike is later succeeded by Charlie Crawford.
- A pro hockey player spends more time with his family after he is forced to retire.
- Randall tries to please visiting Governor Riley. Charlie and Caitlin struggle to keep their affair secret and Stuart senses there's something strange in the office. Carter is getting a foster child.
- As a preemptive strike against illegal drug use, Mike mandates that the staff will undergo mandatory drug testing, then accidentally ingests peyote during a visit with Native American constituents.
- When Tim doesn't just propose another evening with Caitlin but a trip to St.Barts, she has her first real row with Charlie. After the press finds out the mayors limousine was carjacked with him, Paul and Charlie in it, PR demands they spend a night with an officer on patrol in a police car, while Stuart and Carter ride a police horse together; Charlie gets shot -accidentally as a video camera proves, but by...- which brings Caitlin running back to him, only to find out it's just a superficial wound...
- Caitlin finds that Charlie lied, and pulls a prank on him. Charlie dates a mentally unstable woman so that he seems unavailable. Randall offers a job to a high school classmate, now a hobo, to make amends for ruining the man's life.
- Dr. Bronsteen, an old professor of James', is appointed the city's new School Commissioner by Winston, but it is later revealed by the press that he was caught on camera smoking pot at a 1971 Grateful Dead concert causing duress for Mike and disbelief for James. Ashley is offered a job reporting for a local TV station.
- At a mayors' conference, Caitlin feels awkward because Charlie once had an affair with the organizer, so Caitlin tries to make Charlie jealous. Randall renews his long-standing professional rivalry with Mayor Stone Taylor of Los Angeles.
- Caitlin tries to sabotage Mike's date with her visiting sister Catherine. Stuart joins the other staffers in taking an interest in art. Paul is upset to learn that Carter makes more money than Paul does, so Paul starts acting immaturely about the matter.
- Randall tries to impress Claire by having a tree cut down, only to find out that the tree is an historic landmark. And Charlie tells it to a stranger, who turns out to be the campaign manager for Randall's opponent Julian Wheeler.
- President Clinton pays a visit to City Hall, during which James helps Paul to obtain a photograph with the President. Nikki and Carter have a flirting contest.
- Charlie is exhausted from keeping up with his much-younger girlfriend Tracy. Gay art dealer Martin Davis invites Randall, Carter, and Stuart to a fund raiser, where Martin and Carter might hit it off.
- Mike continues his pursuit of Caitlin, despite her engagement to remarry Trevor. Stuart disrupts Carter's hunger strike against an environmental polluter. Randall, Paul, and James try to do maintenance work in the office.
- When Caitlin instigates background checks on the staff, Mike tries to one-up her by staging an internal break-in and stealing the files. Meanwhile, James tries to coach Mayor Winston for an upcoming appearance in an independent film.
- Charlie plays racquetball with Mayor Winston, beats him in a match, and crushes his ego. Paul campaigns to get a raise. Stuart hires an actor to date Carter.
- Paul feels depressed when his divorce is finalized, so Carter feigns heterosexuality to help him play the dating game. Charlie and Caitlin have a flashback to their first meeting - in 1988 during a political event for Michael Dukakis.
- Mike plans a star-studded party for the Mayor's 50th birthday, but tries to keep him away from Holly Cohen, Randall's romantic interest from the governor's office so that the Winston marriage doesn't suffer.
- Mike follows Caitlin to Paris in order to break up her engagement to Trevor. James preps Randall to receive an award that he may not have earned. Stuart asks Nikki to pose for a calendar so that he can donate proceeds to charity.
- Randall delegates Charlie to decide which staff member will move into a beautiful new office. Caitlin tries to find out what the City Hall Santa Claus looks like before she dates him.
- When an old friend of Mike's who's in the navy comes to town, he's happy to see him. Until he learns that he hooked up with Carter.
- 1996–200230mTV-148.5 (213)TV EpisodeMike's political mentor comes to City Hall to help on the Millennium project, and displays a literal Messianic complex. Things heat up between Randall and Janelle. A mishap occurs when Paul dog-sits Rags as a favor to Carter.
- The staff tries to appease Native Americans by having an appropriate float in the Thanksgiving parade, but things go awry. Paul's visiting mother doesn't know that Claudia has left him and he is afraid to tell her.
- An abrasive blind man finds Caitlin dull, spurns her, and causes her to try to improve her personality. In need of a religion refresher, Randall and Charlie accidentally wreak havoc on Claudia's religious education class and her future.