This situation comedy takes place in New York's City Hall. It centers on Mike Flaherty, the deputy mayor, who has to protect the slightly moronic mayor, Randall Winston from those who want to ruin his political career, and from himself, cause he is constantly making an ass of himself and Mike has to try and make sure that his little escapades are either not made public or have very little negative effect on the mayor. Helping Mike is Carter, probably the least quirky member of the mayor's staff and Nikki and James. Stuart and Paul are two members of the staff who cause just as much problems. Mike's secretary, who joined the show during the second season was Stacy. Mike's girlfriend during the first season was Ashley, but the character was dropped, his next girlfriend, during the following season was Laurie, and during the third season it was Nikki, and in the fourth season it was Caitlin Moore, the mayor's campaign manager. Michael J. Fox would leave the show after the fourth season. During the next season, the new deputy mayor would be Charlie Crawford.
The Mayor has a stuttering problem. And Mike has a big problem when he promises to coordinate Paul and Claudia's wedding but discovers that the church is also booked for a funeral at the same time.
After eating some of Rags' dog food, Paul develops a rash before he appears on "The View." Nikki helps him discover the wonders of makeup, though. Stuart tries to convince James that he's gay. Mike hires a hotshot director to film the mayor's Senate commercial, unaware that Trevor is Caitlin's ex-husband. After the commercial turns out to be a flop and Mike fires Trevor, Caitlin accuses him of being jealous. When a talk with Nikki persuades Mike to express his feelings for Caitlin, he sees her and Trevor in a heated embrace.
Mike invites Caitlin to his Christmas party as his only guest but his plans at romance are spoiled when she arrives with a date. Paul finds John McEnroe's headband in the City Hall clothing drive box. James finds a second job as a suicide hotline operator. Stuart installs a chin-up bar in the mayor's office, which the mayor promptly injures himself on.
Mike must choose between protecting his mom, Macy, and protecting the Mayor, when he tries to spin the Mayor out of a new scandal--His Honor's alibi would reveal that he spent the night with Macy instead of a prostitute. Meanwhile, Paul is sued and goes to The People's Court to defend his case.
Mike has a meeting with a tomato stand owner who refuses to move his stand so that the city can build a new performing arts center. He ultimately enlists James to compete against the man in a "pig-off" to decide whether the stand will stay or move. The mayor befriends a rapper who sampled one of his speeches in a song. Paul and Deirdre have memories of having sex at a concert 20 years before, driving Stuart jealous.
The Mayor brings an abandoned baby to City Hall. Mike's old girlfriends voice opinions about him. The Mayor sends James to see a psychiatrist for him, concerning his sexual problems. Mike wants to adopt the baby. The Mayor takes Viagra to help him out. Mike's interview with the social worker doesn't go very well. Nikki prepares to tell Mike about her crush on him, but can't quite get the words out.
Faced with the prospect of spending Valentine's Day alone for the first time in eighteen years, Mike is thrilled when old flame Laurie steps back into his life. But he doesn't know what to do when she discovers a ring Mike was holding for Paul, and assumes it's for her. Meanwhile, Paul plans to propose to Claudia.
When Laurie accepts Mike's proposal, he begins to worry that they are too different. Meanwhile, Paul struggles to get the courage to propose to Claudia, and various staff members fantasize about what their life would be like if they married Mike.
Mike prepares to have sex with Heidi Klum for the first time. After "it", Heidi asks Mike to keep their relationship a secret. James receives his Aunt Sarah's ashes in the mail; his Aunt Sarah was a cow. Mike daydreams while making a statement to the press and accidentally reveals his relationship with Heidi; she breaks up with him. Paul's new fan creates problems for Aunt Sarah (take a wild guess).
A champagne filled New Year's celebration at the Mayor's mansion gets out of control, resulting in more than a little embarrassment the next day, especially for Mike and Nikki. On the big night, Nikki's date, Jay, two-times her and a protective Mike not only gets even--he gets Nikki. Meanwhile, Stuart is undone over the death of his family cat and Stacy makes James question his own virility.
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.
Carter, Nikki and Mike go deer hunting in a fundraising attempt. While Mike is gone, Stuart becomes Stacy's boss for the day. And, with Claudia's help, Paul campaigns for a raise.
Mike discovers that his childhood pal, Nate Scott, has more in common with Carter than meets the eye, and finds it difficult to deal with this revelation. Meanwhile, Paul instructs Stacy in the finer art of being a cheapskate.
While Michael and Caitlin fly to San Francisco, Stuart joins Carter for a protest and the mayor tries to have a light bulb changed.
Mike's mom, Macy, is visiting for a week and she and the Mayor hit it off better than Mike ever imagined, or feared. Meanwhile, Nikki dates Steve, a ventriloquist whose dummy, Mr. Bungle, is more romantic (and talkative) than Steve. And Stacy and Stuart scheme to get Hank, an elderly security guard, his job back after he accidentally shoots Paul.
The Mayor's free-thinking daughter, Meg, with whom he has a somewhat strained relationship, puts the "bare" in bareback when she disrupts a rally with hansom-carriage drivers in Central Park to draw attention to her animal rights stance--and not coincidentally, herself. Meantime, the gang tries to reunite a needy Paul with ex-girlfriend Claudia, but he's smitten with his new pen-pal.
While a reporter visits City Hall to do a story on Paul, the mayor thinks she's really there for him. Mike thinks Carter's boyfriend is hitting on him. The staff looks for good samaritans for a dinner. Stuart tries to convince James that he's getting fat.
The staff prepares for Paul and Claudia's bachelor and bachelorette parties as the city prepares to unveil a new statue that it commissioned. The girls play "I Never....". Paul's party is in the office because the Mayor can't go to strip clubs. The new statue, called "The Bird," is, you guessed it.... The girls think a visiting priest is a stripper because of a prank pulled by Stuart. James and Carter go to the hardware store and it is robbed with them in it. Mike is trapped in the store too, after he goes checking for James and Carter. Stacy sends the guys the male stripper Stuart canceled for the girls.
Mike suggests the staff undergo drug testing to demonstrate the mayor's new anti-drug campaign. But after he accidentally gets high while visiting some Native Americans, he risks failing the drug test that he initiated.
After Mike's picture with model Heidi Klum is in the tabloids, people assume he's dating her. But, he soon is after she asks him out. As a result, Nikki reveals to Carter that she has a secret crush on Mike. And The Mayor can't stop laughing at VERY inappropriate times.
Mike helps the mayor deal with his feelings when his father unexpectedly dies. James thinks Caitlin has a crush on him. Paul's magic eight ball proves helpful to the staff.
Mike celebrates his five-year anniversary working for the mayor by taking Caitlin and going on a joyride with the mayor's '66 Mustang. Nikki and Carter accuse each other of being vain when City Hall ID photos are taken. The mayor wants to rekindle his romance with Janelle. Caitlin's busy schedule forces James back to speechwriting; he hires Deidre to be Mike's new secretary.
A feuding Carter and Stuart become friends with the other's ex, just for spite.