The episode opens with Oliver, Thea, and Quentin celebrating the capture of Adrian Chase, which has restored Green Arrow as a hero and sent Oliver's approval rating through the roof. Quentin says that he's going to find Rene to berate him for missing his meeting, but wishes Oliver a happy birthday before he leaves. Thea suggests they celebrate with a drink tonight, but Oliver says he made plans with Felicity already.
That evening, Oliver heads to Felicity's apartment but finds the door open. He sees an intruder and throws him to the ground...but it's just Curtis as part of Oliver's surprise party.
At the party, Curtis shows off a new sonic enhancer for Dinah (who's working) while Diggle tells Oliver he patched things up with Lyla. Quentin arrives late and mentions that he can't find Rene. Oliver gives a toast and says that he can't remember the last time he actually celebrated his birthday. Diggle says it's usually because they're saving the city from a bad guy or an evil plot this time a year, to which Quentin mentions that it's as if summer break started early for them. Everyone talks about their plans with their time off and then leave the room to give Oliver and Felicity "a moment."
In a flashback, Kovar chains Oliver to the roof of a building in Lian Yu and injects him with a torture drug called the Red Death. Oliver vows to kill Kovar, but Kovar says that Oliver will only want to kill himself after the drug takes hold.
Curtis heads over to Dinah's apartment and notices that someone has broken into her place. He tells Felicity (who he was talking to on the phone) to send backup before he gets knocked out from behind and dragged away.
Diggle and Oliver head to Dinah's apartment, and Oliver quickly determines that Chase is behind it. He finds an arrow shaft in the apartment and tells Diggle that Talia al Ghul must still be working with Chase. Diggle says he'll get Quentin and Thea to a safehouse, while Oliver confronts Chase.
Of course, Chase just laughs at Oliver and says that he's always ahead of Oliver, while Oliver seems to always be behind. Oliver says he's going to find his friends, but Chase knows that Oliver will be back.
In another flashback, Kovar starts to torture Oliver and reveals that the Red Death forces Oliver to relive every pain he's ever experienced. As Kovar starts touching Oliver's scars, Oliver starts remembering every traumatic wound he's ever experienced.
Oliver heads back to the Arrowcave, and tells Felicity that he wants her to stay with him instead of going to the safehouse with Thea and Quentin. Oliver is still worried about his son William, but Felicity says she still can't find any trace of him. Then, Felicity discovers that Black Siren has escaped from ARGUS - and is probably heading straight to the safe house.
Sure enough, Black Siren shows up at the safe house, posing as Laurel. Quentin finds Black Siren and hesitates, giving Artemis the opportunity to knock both him and Thea out. Black Siren does apologize to Quentin before he passes out though.
When Oliver heads to the safe house, he figures out that Chase is trying to take away his biggest strength: his team. Oliver says that Diggle and Felicity need to leave town, so that Chase can't put them in danger too.
In a flashback, Oliver relives all his failures over the last few years. Kovar passes Oliver a gun with a bullet and says that he can either waste the bullet on Kovar or end his own suffering. Kovar says that Oliver won't last more than 14 minutes before killing himself.
Oliver heads back to Chase and beats the snot out of him. Oliver puts a gun to Chase's head, but says that he will never kill Chase or let him go because he won't give him of the satisfaction. Chase says that the only way to save his friends is to let him go, but Oliver says he'll find another way. Chase says that Oliver only has until tonight to let him go, and then says that Oliver is "one loss" away from snapping. Chase asks Oliver who's going to die this year, and then smiles.
Thea and Quentin are chained in the back of a truck, and Thea tries to explain that Black Siren isn't "their" Laurel. Quentin doesn't take the news well, but seems to figure it out before Artemis and Black Siren show up to drop them off at Chase's secret lair.
As Diggle and Felicity leave the city, Felicity says she has a bad feeling in her gut about leaving Oliver alone. Sure enough, Oliver realizes there is an intruder in the Arrowcave....MALCOLM MERLYN. Merlyn says that he's there to help Oliver save Thea.
Meanwhile, Talia confronts Diggle and Felicity as they try to leave town. Diggle tries to run her over, but it was just a trap to get the car to crash. Felicity and Diggle survive, but are apprehended by the League.
Oliver and Merlyn arrive at the scene of the car crash. Merlyn wants to bargain with Chase, but Oliver still wants to find another way and he'll do it by himself. Merlyn says that Oliver can't be an island, and that he'll always have human connections. Oliver leaves to make sure that Chase's prison transfer goes smoothly and tells Merlyn to figure out where his friends are.
In a flashback, Oliver sees a hallucination of Yao Fei, who reminds him of all his failures over the last few years. Yao Fei says that everyone suffers around Oliver and then tells Oliver to kill himself to prevent any more suffering.
In the present day, Black Siren puts Quentin in a shipping container. She's surprisingly kind to Quentin and says that she's only helping Chase because he freed her....and because Chase agreed not to hurt Quentin. Quentin tells Black Siren that his Laurel wouldn't be that stupid, and Black Siren seems to agree with him.
Oliver watches Chase get carted away. Chase says that the second he gets on the prison helicopter, all of Oliver's friends will be dead. Chase also says that Oliver's about to get a phone call. Sure enough, Oliver gets a video call....revealing that Chase also has William.
Oliver chases after Chase, but Argus has already taken him to the transfer site. Malcolm shows up and says he figured that Chase went after Oliver. The two take down a ton of Argus guards, just so Oliver can confront Chase. Oliver asks why Chase brought William into it, and Chase implies that it's because Oliver got Chase's wife involved. Before boarding the helicopter and escaping, Chase tells Oliver he'll see Oliver on "the boat."
Back in the Arrowcave, Oliver says that he's trying to track down Chase via Felicity's computer system. Oliver also reveals that he's called in backup, via Nyssa al Ghul. Of course, Oliver didn't tell Nyssa that one of their adversaries is her sister Talia. Felicity's computer goes off, revealing Chase's location.
One plane ride away, Oliver, Nyssa, and Malcolm fly towards the site of their final showdown with Chase: Lian Yu.
In a final flashback, Oliver prepares to pull the trigger, but a hallucination of Laurel convinces him not to do it. Laurel says that his friends and family still need him. So instead of shooting himself, Oliver shoots the lock of his cell and walks out.
Chase dumps Oliver's friends on Lian Yu and says that he's counting on Oliver showing up to rescue them. Felicity says that Oliver can't beat Chase's small army alone.
Of course, Oliver isn't done collecting allies. When he lands on Lian Yu, he heads down to the secret Argus bunker and asks Lian Yu's sole resident for help. SLADE WILSON looks up from his cell and says that he's glad that Oliver returned.