Caitlin and Charlie fight the attention of Caitlin's new friend. Carter, Stuart and Paul compete for a trip to New Orleans with the mayor.
s05e01 - Hello Charlie
s05e02 - Smile
s05e03 - The Spanish Prisoner
s05e04 - The Bone Collectors
s05e05 - Blind Faith
s05e06 - Balloons over Broadway
s05e07 - Lost and Found
s05e08 - All the Wrong Moves
s05e09 - The Burgers of Wrath
s05e10 - Toy Story
s05e11 - The Perfect Dorm
s05e12 - Hey Judith
s05e13 - The Gambler
s05e14 - In the Company of Dudes
s05e15 - The Image Maker
s05e16 - Trainstopping
s05e17 - Rain on My Charades
s05e18 - You've Got Male
s05e19 - Minor League
s05e20 - Science Friction
s05e21 - Brotherly Love
s05e22 - A Shot in the Dark (1)
s05e23 - A Shot in the Dark (2)
In New York's City Hall, Mike Flaherty, the deputy mayor, 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.