- Crosses the Line Twice: Some of Kane's maneuvers and shenanigans are so sleazy, disreputable and sheer effective that they become this.
- Darkness-Induced Audience Apathy: The entire cast is so morally wretched and corrupt, with no one striving to be better or to work for the benefit of Chicago, instead just seizing power, that it's hard for audiences to care what happens in the election or with the politics.
- Love to Hate: Nobody would want a morally bankrupt official like Kane, a criminal past redemption, as mayor in real life, yet some of his relatively harmless maneuvers and shenanigans are so sleazy, disreputable and sheer effective that they are funny. When he wins a battle, it's often awesome and terrifying at the same time.
- The Woobie: In this series it's a relative term, but Mona and Emma qualify.
- Mona knew Chicago politics would be rough, but not that rough. Her main goal is to improve Lennox Gardens, her community. For this she gets completely taken advantage of by Tom, has her privacy invaded, is the fall guy to Lennox Gardens residences, has her family threatened, and is forced to leave town.
- Emma is raised by two parents who put their political ambitions ahead of her. As a result she develops, then kicks, a drug habit and tries to redeem herself by running a clinic for the disadvantaged. Her mother doesn't even pretend like she cares about her and her father throws her under the bus to save his own ass.
YMMV / Boss