Stuart is the assistant deputy mayor. He is in charge when Mike or Charlie are away. Stuart often acts sexist, boorish and rude to his colleagues, masking low self-esteem, which everyone's aware of and likely why they deal with his antics. Despite this, Stuart is smart and capable, albeit too into winning and politics, rather than affecting conscientious change. He often gets snubbed by women because of his sleaziness and depravity, so much that he often solicits sex.
In 1996, Stuart works as Deputy Mayor Mike Flaherty's Chief of Staff at City Hall. He pretty much runs over the sweet and innocent James and the bumbling Press Secretary, Paul Lassiter, while being sexist to Nikki, although she and Janelle constantly show Stuart up in his running commentary on them. When Carter Heywood speaks out against the administration and ends up getting hired by Mike, Stuart is faced with someone incredibly capable, smart and competent who doesn't give Stuart's crap the time of day. This puts another balance to the office, as Stuart doesn't get to rule over the male staff in the same manor as he'd previously attempt.
While clear antagonists from the start due both to Stuart's homophobic running commentary, but more so his insecurities about Carter being the more competent political mind, the guys end up roommates and even become friends eventually.
Stuart constantly vies for Mike's job, although he is also constantly checked by Mike's capabilities. Despite this, Stuart does provide political insight and help, being rather dedicated to doing his job well.