Mike's choice for a new campaign manager, Caitlin Moore, is more than he expected and her ambitious nature quickly becomes a direct threat to his authority.
Caitlin tries to fire James and take over his speech-writing duties; guest Nipsey Russell.
Mike plans an internal break-in to obtain background files on staffers at City Hall.
Mike deceives Nikki into going to couples counseling with him; eighth-graders challenge the mayor to take a standardized test.
An interviewer for a gay magazine misinterprets Mike s comments about his closeness to the mayor.
Former Sen. Alfonse D Amato advises Mayor Winston, who considers giving up his bid for the Senate.
Mike targets a wealthy political donor (Amy Irving) to help the mayor s bankrupt Senate campaign.
The mayor falls into an adjacent pit during a rescue operation to free a trapped baby.
Mike and Caitlin pose as a couple to win an endorsement for the mayor from a senator with a sentimental streak.
Mike deals with an angry doormen s union; Paul opens a politically themed restaurant.
Mike and Caitlin take the mayor s convertible for a joy ride.
Mike invites Caitlin to his Christmas party but doesn t expect her to bring a date.
Mike goes on a date with Caitlin s sister; Stuart takes up art.
Mike must raise $500,000 when a ticket glitch in a raffle results in hundreds of winners.
Mike hires a British director for the mayor s political advertisements.
Caitlin s new romance with her ex-husband drives Mike crazy.
Mike suspects Carter s new boyfriend is coming on to him; Paul tries to impress a reporter.
Angry farmers protest the mayor s latest proposal; Stuart learns his girlfriend had a fling with Paul long ago.
Mayor Winston seems unaffected by his father s death; James believes Caitlin is attracted to him.
The staffers drown their sorrows in a bar while the president visits the mayor.
Sparks fly between Mike and Caitlin during the mayor s listening tour.
Mike continues to pursue Caitlin despite her engagement; Carter heads a hunger strike against an environmental polluter.
Mike pursues Caitlin to Paris to declare his love before she marries Trevor.
Mike tries to prove that his attraction to Caitlin goes beyond the physical level.
Mike decides to take the fall for a mob scandal in order to protect the mayor and his administration.
Caitlin and Mike declare their love for each other.
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