Spin City
Workaholic Mike Flaherty is the Deputy Mayor of New York City, serving as Mayor Randall Winston's key strategist and much-needed handler. Mike runs the city with the help of his oddball staff: an anxious and insecure press secretary; a sexist, boorish chief of staff; an impeccably groomed gay activist running minority affairs; a sharp and efficient, man-crazy accountant; and an idealistic young speechwriter. Like Mike, they are all professionally capable but personally challenged.

Season 6 · Episode 2 ·
A Tree Falls in Manhattan (2)
The mayor has a tree cut down to impress his new girlfriend. Unfortunately, it was a tree planted by George Washington in 1796. Meanwhile, Charlie has a one-night stand, who turns out to be a rival mayoral candidate's campaign manager. Mike helps out with crisis control. Charlie and Caitlin decide to be friends for the time being, while Mike announces his return to City Hall.
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Episode 2 of season 6 of Spin City: “A Tree Falls in Manhattan (2)”. Aired 2001-09-25. Watch it online free on ZapFlix.