Season 2, Episode 4:
The latest number is Riley Cavanaugh, a hitman for the Irish Mob who becomes a target himself when it's discovered that he's courting a woman his boss wants to seduce. Reese must do what he can to save both of them after Riley kills his former employer's son in self-defense, and the young lovers find themselves on the run from the mob and the police.
Tropes in this episode:
- The Atoner: Riley for killing his lover's husband before they started dating.
- Beware the Quiet Ones: Elias says that bosses like Massey are a thing of the past. It's the hidden boss who acts behind the scenes that you need to watch out for. With a touch of irony, Finch can only agree.
- Bulletproof Vest: Saves Reese's life when Riley shoots him.
- Cardboard Prison: Implied; Elias is still running his empire from prison, and ordering the guards about like his own mooks.
- Character Development: "I haven't eaten there since they remodeled, but they used to have a rib-eye to die for." Compare that statement, which Finch offered to Reese without hesitation, to the discussion about the breakfast menu in a diner at the beginning of "Judgement" in the previous season.
- Contract on the Hitman: The mob is on the hunt for Riley, one of their contract killers.
- Go-Karting with Bowser: In exchange for his help on getting the hit on Riley cancelled, Elias asks Finch to... drop by on occasion and play chess with him.
- I Can Change My Beloved
- Laser-Guided Karma: "I'm not here for the money."
- Meaningful Echo: Finch says that Riley is "bad code". Realising he's just used the same term as Root clearly upsets Finch, and he later rejects the analogy, because Riley has changed while software cannot.
- Nothing Personal:
- Not So Different: Reese strongly identifies with his Shadow Archetype Riley. Also Elias and Finch, given their mutual role as The Chessmaster.
- Offhand Backhand: Reese does this to one of the mooks during the rooftop fight.
- Redemption Equals Death: Riley. There was only one train ticket.
- Smart People Play Chess: The only thing Elias wants in exchange for his help is for Finch to play chess with him.
- Trojan Prisoner: Reese and Riley pull one of these off to save Annie.