With Star City going bankrupt Oliver is desperate to end Cayden James' reign of terror and is forced to make a tough choice that puts him at odds with Dinah.
- A Death in the Limelight: The episode's flashbacks focus on Dinah meeting Vince, and their time undercover at Sonus' operation, right up until the particle accelerator explosion. Vince is killed by the episode's end.
- Batman Gambit:
- Cayden deliberately turned Vince's comms back on to provoke Team Arrow to split up to try and save him. The end result is that both the attempt to secure the thermobaric bomb and the rescue mission fail.
- It's suggested that Cayden's entire campaign is one of these on the part of an as yet unknown villain; they sent Cayden doctored proof that Oliver accidentally killed his son, provoking his attacks on Star City.
- The Bus Came Back:
- Alena returns, helping Felicity hack into Cayden James's database.
- Sean Sonus returns via flashbacks.
- Cold-Blooded Torture: After being exposed as a mole, Vince is subjected to this by Diaz and Anatoly. His Healing Factor prevents any permanent damage, but it still obviously hurts.
- Continuity Cameo: Captain David Singh is seen in the flashbacks.
- Cruel and Unusual Death: Black Siren screams into Vince's head until either his skull is shattered or his brain is liquefied.
- Downer Ending: Team Arrow didn't get the bomb, and Vigilante is murdered. The only silver lining is that they find the "evidence" of Oliver killing Cayden's son — they can prove it was not Oliver as the type of footage was digitally framed just like it was when his secret was nearly exposed way back at the start of the season.
- Even Evil Has Standards: In a reverse from their stances earlier in the season, Black Siren balks when Cayden orders her to execute the immobile and helpless Vince in front of Dinah. She goes through with it under threat, and when the deed is done, she looks almost sickened with herself.
- Failed a Spot Check: A computer genius like Cayden James somehow missed the fact the "evidence" of Oliver murdering his son was digitally doctored.
- Forced to Watch: Once again, a villain forces Dinah to watch Vincent die in front of her very eyes.
- Foreshadowing: Based on the episode's title, you can probably bet things won't go well for the heroes.
- Freak Out: Black Siren has one when Quentin confronts her with pictures and videos of Earth-1!Laurel. She goes from visibly moved to panicking, muttering "this isn't me" before letting out a Canary Cry to destroy the projector and running off. Her demeanor later in the episode implies that the experience was still affecting her.
- Good All Along: Yes, Vincent was serious about being a mole on Cayden's team.
- Heroic BSoD: Dinah has one after seeing Vigilante die right before her eyes.
- Hidden Villain: The same person who outted Oliver as the Green Arrow in the premiere sent Cayden James doctored evidence to make Cayden think that Oliver killed his son. Who this person is and why they've done this is unknown, although Team Arrow speculates that it was someone who knows Cayden well enough to know how he'd react to Oliver "killing" his son.
- Hope Spot: Quentin and Thea were starting to get quite optimistic about the idea of redeeming Black Siren. Then she murders Vince on Cayden's orders, which seems to dash their hopes. Ironically, judging from her hesitance to kill Vince and unsettled expression afterwards, they likely did succeed in getting through to her to some extent.
- Hypocrite: Dinah accuses Oliver of this when he tries to stop her from saving Vincent in favor of the bomb, arguing that if Felicity or Lyla's lives were on the line, there wouldn't even be a debate about this.
- Ignored Epiphany: Laurel, despite being reached out to by Quentin and being obviously uncomfortable with James's request, still goes through with brutally executing Vincent.
- Internal Reveal: Team Arrow finds out about Vigilante's Double Agent status... right as they are about to apprehend him.
- It's Personal: Black Siren kills Vigilante right in front of Dinah's eyes meaning that Dinah is hell-bent on killing her.
- Jerkass Has a Point: Dinah takes Oliver's refusal to rescue Vince instead of securing the bomb as nothing but callous hypocrisy, but Oliver's proven right shortly after: not only does the rescue mission play into Cayden James' hands, it fails, Vince is killed, and because the New Recruits left to save Vince, Oliver and Diggle didn't have the manpower to secure the bomb.
- To Dinah's credit, she is not wrong either when pointing out that if it was Felicity or Lyla being tortured this would not even be a discussion.
- Jumping Off the Slippery Slope: Dinah believes that Vigilante's extremism was right and proclaims she is going to kill everybody in Helix — starting with Black Siren.
- Kick the Dog: While Cayden wanting to kill Vigilante is somewhat understandable (Vince had been a mole, and he killed Sheck), but having Black Siren do it in front of Dinah while the latter is pinned and helpless is unnecessarily cruel. Even Black Siren hesitates at the idea.
- Leaning on the Fourth Wall: It has been over a week since Cayden James' began holding the city hostage.
- Love at First Sight: In the flashbacks, it is shown that Dinah and Vince pretty much instantly fall for each other during their first meeting.
- Lured into a Trap: Both the Outsiders, as well as Oliver and John are lured into their respective positions with a surprise waiting for them that scrutinizes their plan.
- Misblamed: Dinah, in her grief, is quick to blame Vincent's death on Oliver for not helping her save him.
- The Needs of the Many: Oliver is more concerned with stopping the bomb than saving Vigilante; the New Recruits disagree. This disagreement gets Vincent killed and causes Team Arrow to lose the bomb.
- Obvious Judas: Cayden James even mentions how unlikely it seemed from the start that a vigilante, hell-bent on clearing the streets of crime, would team up with the likes of him to target other vigilantes.
- O.O.C. Is Serious Business: Black Siren is usually ecstatic at killing people, but she is extremely hesitant in killing Vigilante — but unlike in "Irreconcilable Differences" Cayden James is watching her every move and when push comes to shove she does the dirty deed.
- Out-Gambitted: Oliver tried to get A.R.G.U.S's help to evacuate the city, but Cayden James was prepared for them too.
- The Password Is Always "Swordfish": Felicity guesses that Cayden James's password is the birthday of his deceased son. She is correct.
- Properly Paranoid:
- Cayden James never truly believed that Vigilante joined Helix just to take down the other vigilantes in town, but kept him because he was useful, but began doubting him after he kept meeting with Dinah.
- While Vince assures the team that his Healing Factor will prevent him from facing any serious danger, the ending shows that they were right to be worried.
- Redemption Equals Death: This episode has Vigilante at his most heroic (for a given value of "heroic"; he shows no remorse for trying to kill Oliver in the past and it's implied that he hasn't moderated his views on other criminals). It ends with his death.
- Roaring Rampage of Revenge: In retribution for Vincent's death, Dinah vows to kill every last one of Cayden James' cabal, with Back Siren being first on her list.
- Rule of Symbolism: As Black Siren insists "this isn't me", she's standing in front of a projector that imposes Laurel's face (wearing the Black Canary mask, no less) over hers.
- Sadistic Choice: Anatoly set up in the warehouse where the bomb one was: save innocent hostages or stop the bomb. Diggle saves the hostages while Oliver goes after the bomb itself, but unfortunately is quickly out numbered.
- Senseless Sacrifice: Dinah believes Vince's death was for nothing; Oliver disagrees as he finally has his first best shot at stopping Cayden thanks to the intel they got with Vince's help. Unfortunately, Dinah doesn't see it that way and intends to avenge his death by personally murdering Cayden and his cabal.
- Shout-Out: Cayden James holding Star City hostage with a bomb that's constantly moved throughout the city is like what Bane did in The Dark Knight Rises.
- Shut Up, Hannibal!: Oliver destroys the walkie-talkie to Anatoly while he is speaking, clearly not caring about whatever evil speech his former friend has to say and instead focusing solely on his mission.
- Spotting the Thread: Everyone in Helix is quick to note that Team Arrow would never have killed Sheck ... so all eyes begin to turn on Vigilante.
- Stealth Hi/Bye: Laurel keeps following Quentin and always vanishes the second he turns around.
- Tempting Fate: Both Dinah and Vincent make a big deal of not trying to lose each other again. Tragically, Vincent ends up dead for real this time...
- Torture Technician: Ricardo Diaz and Anatoly take turns torturing Vincent.
- True Companions: The New Recruits are firmly established as this; when Dinah insists on leaving to try and save Vince, Curtis and Rene join her, regarding her as family. Of course this can be seen as a Deconstruction since they are essentially turning their back on the city to save one man.
- We Used to Be Friends: After being estranged, but civil it's made clear that Oliver and Dinah are no longer friends — because she blames him for Vincent's death.
- What the Hell, Hero?:
- Oliver subtly calls the New Recruits out for refusing to help them find the bomb.
- Dinah tries something like this to Oliver but it's clear it's more she's pissed at Vincent's death then anything else.
- Wham Episode: Vigilante dies and it's revealed that the person who leaked the doctored image of Oliver being the Green Arrow is the same one who sent Cayden James the "evidence" of Oliver killing his son.
- Yank the Dog's Chain: Black Siren killing Vigilante really puts a damper on Quentin's hopes to reform her.
