- Hilarious in Hindsight: Amusingly, the show did predict the eventual decentralization of Wall Street in the pilot, via a pair of investors who invite the characters to join them when they sail down to the Caribbean and trade stocks online.
- Romantic Plot Tumor:
- Jack and Alex's "will they, won't they" plotline continues long past the point when they explicitly agree to each other that they're separated, and takes up more and more screentime in episodes as a result.
- McConnell and Sherman's sister, Gillian. The former has been fired by Divack, and the latter is cheating on him with other men and contributes nothing to the A-plot, but their scenes take up a substantial part of the final two episodes.
- Unintentional Period Piece: Aside from the World Trade Center being featured in the pilot episode, the show is a storm of pop culture references to works like Gattaca, Xena: Warrior Princess and Buffy the Vampire Slayer.
- Values Dissonance: One episode has Mitchell play host to a Saudi Arabian investor and his daughter, who is sexually repressed and wants to lose her virginity with him, after removing her hijab when they're alone. Later on (after they've done the deed), her father goes to him and says that he'll kill him if he touches his daughter. This whole plotline is Played for Laughs. After a decade of honor killings of women who cheat or disrespect their families in Middle Eastern societies, the episode comes off as incredibly tasteless and inflammatory.
- The Woobie: McConnell. He loses $500,000 on a bad trade with Alden Industries because he became impetuous, gets no bonus at the end of the year, gets chastized (and later fired) because of insider trading), his relationships almost always fail, and the one woman who shows genuine interest in him is not only playing him for his connections, but is cheating on him with multiple men.
YMMV / The Street