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I think you'll find that brute force, while it's easy, is exceedingly messy. I prefer precision - design over chaos...
~ Cayden James
There’s no such thing as insanity. Revenge, on the other hand, is very real.
~ Cayden reveals his motivation.

Cayden James is a major antagonist in Arrow, appearing in the fifth season and returning as the secondary antagonist of the sixth season. He is the leader of the hacktivist organization Helix. After being freed from A.R.G.U.S. captivity at a black site facility, James starts going rogue and allies himself with Black Siren and a cabal of several other villains. He develops plans for an operation called "Arclight", which might result in the death of 300,000,000 people. As Cayden states to Oliver Queen, his motivation is that the Green Arrow cost him his son.

He is portrayed by Michael Emerson, who also portrayed the Joker in The Dark Knight Returns, Benjamin Linus in Lost and Zep Hindle in Saw.

Biography

Past

At some point in his life, Cayden had a son, Owen, whom he loved very much. After Cayden and his wife separated, he remained in contact with her still.

Cayden is a skilled hacker and founder of the organization Helix, in which he united hackers for political activism. Helix was an immensely successful group and obained a large data bank of delicate files on many important and influential people. However, his work at Helix clashed with his personal life and as a result, Cayden's relationship with Owen suffered.

On one occasion, Cayden personally caused a pharmaceutical group to lose all the money they made in an illegal black market deal. However, in doing so he missed the basketball game of his son Owen. After receiving a reminder, Cayden immediately drove to Owen's school but came too late. He met with his son after the match was already over and tried to act as if he had been at the game. However, Owen replied that he did notice Cayden's absence and that Cayden should not lie. The two started talking about Owen's mother and her new boyfriend Jim and Cayden seemed glad that Jim treated her right. Addressing the elephant in the room, Cayden then apologized for not making it to the game, claiming that he got caught up at work. However, Owen replied that Cayden never even really explained what his work was - other than secretive and important. Cayden then promised his son that he would like to be a bigger part in the life of his son from now on. He promised to be there at the finals and, although he could not share all of the details of his work, also promised to be a bigger part of Owen's life - starting the next day.

CaydenArrested

Cayden is arrested by A.R.G.U.S.

Eventually, A.R.G.U.S. showed interest in Cayden James after noticing Cayden's take-down of the pharmaceutical company. Considering him to be twenty times more dangerous than Edward Snowden, should he start to leak information, A.R.G.U.S. made efforts to capture him. Although he was warned that A.R.G.U.S. might be after him and that he should not show himself in public for some time, Cayden headed out anyways to be there during his son's match. Right outside the gym, Cayden was apprehended by two A.R.G.U.S. agents who told him that they had come to take him into custody. Cayden acknowledged the situation and claimed that he had been warned. He explained that his only son was playing inside and asked for a few moments so that he could fulfil his promise and watch the game. However, the agents refused and, sad that he would have to disappoint his son, Cayden let himself be arrested without causing any problems. He was not aware that he would never see his son again.

Cayden was never prosecuted legally but instead kept at a black site without a trial. He was kept imprisoned as a "person of interest" under order of Amanda Waller. While captive, Cayden was informed by an A.R.G.U.S. agents that his son was found murdered. Overwhelmed with sorrow, Cayden panicked and demanded to know who would hurt his innocent boy.

Freed by Helix

Eight months later, Helix managed to locate the black site where James was being imprisoned. As that point, one of the Helix members - Alena - also had contacts to Team Arrow member Felicity Smoak and recruited her to assist in the attempt to free Cayden. Although Team Arrow tried to prevent it, they were tricked by Helix and Helix managed to infiltrate the prison area and locate Cayden James. After obtaining James and escaping with him, Helix cut off ties with Felicity, considering her ties to Team Arrow a liability.

Cayden James in captivity

Cayden as an A.R.G.U.S. captive.

It is revealed that the death of his son - combined with his imprisonment - strongly changed Cayden James and turned him into a bitter and cynical villain. In addition, while being hidden at Corto Malteze, Cayden received information with evidence that supposedly reveals that Cayden's son was killled by the Green Arrow. Heartbroken and fueled by anger, Cayden made it his prime goal to make the Green Arrow suffer, planning to target the city the vigilante loves so much in order to fulfil his goal.

Having learned about the battle on Lian Yu, James sent his henchman Sheck there with a helicopter. He arrived on the island and found it in ruins. However, he found a wounded Black Siren and saved her from the island, marking the start of a criminal partnership between the two. After Black Siren has destroyed the Star City Police precinct, which may have been on James' orders, she starts murdering seemingly random people in Star City and takes her fingerprints.

"Attack" on the Internet

Meanwhile, Felicity is contacted by Alena, who asks her for help. She reveals to Felicity that Cayden James is working on something terrible that will hurt the entire world. She claims that his A.R.G.U.S. custody changed and broke him and that although Alena doesn't know exactly what James is planning, she saw one of his casualty estimates which anticipated a death rate of four percent of the world's population - over 300,000,000 people - should James' plan come to fruition. Although Cayden is currently at Corto Maltese, Felicity and Alena plan to hack into his server. In order to do so, they plan to head to the former headquarter to find a way.

At the former Helix headquarter, Felicity and Alena find out that James is planning an operation called "Arclight". Suddenly, several people including Cayden James, Sheck and Laurel Lance enter the room. Cayden reveals that he has come for Alena and reveals his disappointment in her, not for her betrayal but because he could easily trick her into believing that he was still at Corto Maltese. James then addresses Felicity, apologizing to her that she will sadly become collateral damage and calling it a horrible waste of talent. He tells Sheck to kill both women but before they can do so, Green Arrow (John Diggle) and Team Arrow arrive and attack James' henchmen. Although they can take down the henchmen, Alena is shot by a stray bullet and James is able to get away.

James Inner Sanctum

Cayden's team infiltrates the IDND vault.

Laurel's three victims are revealed to be undercover agents of the International Domain Name Directory, the global internet infrastructure. Felicity realizes that the fingerprints of the victims might be used by Cayden James to enter the "master vault" of the IDND in order to destroy the entire internet, which would result in catastrophic damage to the entire modern civilization.

Indeed, Cayden and his team have arrived at the location of the IDND vault. On their way in, Laurel murders a wounded security guard, much to the displeasure of Cayden James. When Laurel rudely tells him that she is not questioning his methods, Cayden calmy tells her that he expects a little bit more gratitude - after all she would have starved on Lian Yu if it were not for him. James then hands Laurel and his chief henchman a film with one of the fingerprints, and all three use their fingerprints to gain access to the IDND vault. Impressed, Laurel claims that he is full of surprises and Cayden replies that he is just beginning. As the villainous team ventures inside, Cayden welcomes them into the "Inner Sanctum".

Soon after, Team Arrow arrives as well. Felicity swiftly realizes that Cayden has uploaded a virus onto the servers which will cause them to explode in six minutes. As Felicity starts to counter-hack the system, the group is attacked by Cayden's mercenaries. Meanwhile, at a safe place inside the vault, Laurel informs Cayden that his men have engaged the targets. Cayden corrects her, claiming that their men have engaged the targets - their partnership is a democracy, after all. Cayden then realizes that Felicity has appeared on the server and swiftly codes something together that will occupy her while Cayden takes his leave. He tells Laurel to do the same for Felicity's companions and then leaves the server room. Ultimately, Felicity is able to reach the server room, allowing her to stop Cayden's virus. However, this seems to have been Cayden's plan from the start, as Felicity has left her digital fingerprints all over the server. Meanwhile, Cayden is able to upload a critical piece of code to Arclight, planning for Felicity to take the fall for it.

Stealing Explosives

As another part of his plan, Cayden has Black Siren and several mercenaries break into a PLACE. While they head inside, Cayden observes them from his headquarters and keeps contact with Laurel in case things go wrong. He also uses his skills to get the group inside the building swiftly and silently, annoying Laurel who complains that she did not get to kill anybody. Cayden reminds her that homicide is not their objective and warns her that two guards are inside the next room. When Cayden is busy hacking the electronic security system, Laurel once more gets annoyed because he is taking longer than she expected. Cayden claims that the younger generation is too impatient and then opens the door for her. While doing so, he quotes Shakespeare - "Cry havoc, and let slip the dogs of war..." - only to tell Laurel that this was a quote and not a directive when she and her men slaughter the guards inside.

CaydenComputers

Cayden keeps watch on Laurel's heists.

Cayden then guides the group through the room where they arrive at a sealed container. Laurel wants to burst it open with her scream but Cayden stops her, telling her that the container is secured with highly-explosive nano thermite. Laurel does not even let him finish his sentence and screams at the container anyways, blasting open the container without damaging the nano-thermite.. Although Cayden is glad the thermite is safe, he claims that he hopes Laurel realizes how this could have gone completely wrong. Laurel and the gang then flee with the stolen nano-thermite. Team Arrow later manage to track Laurel down to an AmerTek facility where she is searching for an accelerant for the thermite. Once more, Cayden keeps surveillance from his high-tech hacking hideout. The team storms the building where they are immadiately attacked by James' mercenaries. While her remaining men flee with the accelerant, Laurel uses her scream to detonate some of the explosives, allowing her and the goons to escape with the thermite.

Back at the Arrowcave, the team learns from felicity that with the two components, Cayden James could build a powerful thermobaric bomb. The team deduces that James will use it in a highly populated area to maximise casualties. They soon come to the conclusion that James might target a concert being held the very night, a conclusion that is proven true when Felicity finds out that Cayden James has already taken over the system there.

Meeting the Green Arrow

When the owner of the concert hall, which holds 35.000 people, refuses to cancel the concert, combined with Diggle being unable to be the Green Arrow that night due to being in hospital, Oliver is forced to don the green hood once more.

During the concert, Team Arrow sneaks into the concert hall and starts looking for the bomb. They soon find that all doors have been locked by fake polcemen, who are working for Cayden James. While Mad Dog, Mr. Terrific and Black Canary head out to deal with the policemen, Oliver heads deeper into the building where he finds the "bomb". Looking at the video feed from Oliver's hood, Felicity immediately realizes that the bomb is only a decoy, which is confirmed by Cayden James who steps into the room as well. He sarcastically claims that Oliver must surely wonder where the bomb is located and claims that the evening will be very insightful for the both of them.

CaydenMeetsOliver

Cayden meets Oliver.

Once more, Oliver demands to know where the bomb is and Cayden tells him the same quote he told Black Siren earlier about this generation's impatience. Oliver fires an arrow at him and Caden deflects it with the prototype of Mr. Terrific's T-Sphere Black Siren stole from the Arrowcave. Cayden reveals to Oliver that there is no bomb - it was all a trick to get the Green Arrow's attention. He outright tells Oliver that he wants revenge on Oliver. Oliver is surprised and claims that he never even met James. James replies that Oliver cost him somethign very dear nonetheless - his son. He then coldly states that he only arranged this meeting so that, when Star City burns, Oliver will know the reason. He then hurls the T-Sphere at Oliver who destroys it with an arrow. Before he can intercept Cayden James, Black Siren suddenly appears and allows Cayden to escape while she battles Oliver.

Back at the Arrowcave, the team wonders whether James really lost a son. They find out that there is someone called Owen Post, who has Cayden listed as his father in his birth certificate and went missing soon after Cayden was taken by A.R.G.U.S., but they cannot find and proof that he ever lived with Cayden or had a close connection. It is also revealed that James had another reason for the "attack" on the concert. He now has video footage of the entire team attacking policemen, which he immediately puts on the internet - without the fact that these policemen were not real policemen. This means that the day the city is voting on an anti-vigilante-bill, footage of vigilante's attacking police forces is circulating. This leads to the anti-vigilante-vote passing with an overwhelming majority, making life harder for Team Arrow.

Kidnapping Quentin Lance

CaydenBlackmails

Cayden blackmails Oliver.

On Cayden's orders, Laurel kidnaps Quentin Lance. She leaves a cellphone which is eventually handed to Oliver. The moment Oliver gets the phone, it rings. Cayden tells Oliver that he has Quentin but will not reveal where he is. When Oliver asks what Cayden wants, Cayden reveals that he wants Oliver and the team to steal a device for him. The device is secured at A.R.G.U.S. and Cayden threatens to kill Quentin if Oliver refuses. Although Oliver is hesitant to help Cayden, remembering that Cayden's ultimate plan is to destroy the city, he does not have a choice if he wants Quentin to live. Cayden reveals that he will text an address to Oliver the next night and that Oliver has to be there with the device if he wants Quentin back alive.

After Team Arrow succeds in their A.R.G.U.S. heist and successfully steals the device, Cayden sends them the address for the drop-of. While they wait, Team Arrow realizes that the device they stole will increase the blast of Cayden's bomb so that it will destroy far more than just the city. In order to save Quentin anyhow, Oliver orders Curtis to tamper with the device so that Cayden will not be able to use it.

However, Cayden underestimates Laurel's connection to Quentin and that her father died when she was thirteen. While Quentin is her captive, Laurel bonds with Quentin enough to recognize her father in him. After their conversation, Cayden enters the room and tells Laurel that it is time for the deal. He reminds her to kill Lance if Oliver fails to deliver the device. Cayden then sends Oliver the location of the drop-off.

JamesMercenaries

Oliver arrives for the deal with Cayden.

Once Oliver and his team arrive, they find Cayden and several henchmen inside the warehouse. Oliver demands that Cayden tells him where Lance is but Cayden wants the device first. When Oliver repeats his demand, Cayden calls it a fair request and offers Oliver to let him speak with Quentin if Oliver drops his bow. Oliver complies and once his bow is dropped, Cayden hands him a phone. Through the phone call, Oliver has proof of life and in turn, Cayden demands the amplifier. Oliver hands him the device but Cayden refuses to take it, claiming that he wanted an amplifier that was not sabotaged. This takes Felicity by surprise, as she did not believe that Cayden could notice the sabotage just by looking at the device. Cayden orders Black Siren to kill Lance and orders his mercenaries to kill Oliver, fleeing from the warehouse while they attack. However, Laurel doesn't go through with killing Lance and instead tells him to run. She cuts him free and allows him to escape.

Back at their headquarter, Oliver tells the remainder of his team that they need to find out how Cayden James realized that the device was sabotaged. The solution is revealed at Cayden's headquarter, where Cayden is watching live video feed from the Arrowcave - he had Black Siren secretly install cameras when she attacked the cave two months ago. Cayden claims that things worked out even better than anticipated. While more people step into the room, Cayden's full team - consisting of Black Siren, Anatoly Knyazev, Ricardo Diaz, Vigilante and Sheck - is revealed; all villains that pestered the team for the last few months are in fact working together under Cayden's command.

Obtaining the Port

Together with Diaz, and Black Siren, Cayden arrives at the office of the Jerry Bertinelli, head of the Bertinelli crime family. Bertinelli states that the three don't look good and asks how they got past his men. Black Siren states that she "blew them a kiss" and Cayden states that Jerry is the last of his kind - the rest of the Bertinelli family is either imprisoned or dead.

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Cayden threatens Bertinelli.

Jerry sarcastically asks whether Cayden is writing a book and Cayden then claims that he heard that sometimes, ships are on Bertinelli's list that never arrive at the docking station. Diaz completes the sentence, claiming that other times, ships appear at the docking station that are not on Bertinelli's list. Bertinelli claims that if the price is right, they can make some sort of deal. Cayden reveals that Jerry misunderstood them - they came to buy the port. Jerry states that the port is not for sale and orders them to leave but Black Siren blasts him into the wall of his office with one of her screams. Cayden then tells Bertinelli that he has 48 hours to reconsider, else they will be back. He also reveals that he knows Bertinelli has a daughter.

While at a warehouse with Sheck and Black Siren, Cayden senses that something is off with Laurel. He asks her and she reveals that she is annoyed that they do not just take the dock from the Bertinellis as they have enough manpower to do so. Annoyed himself, Cayden states that they do as they do because brute force will draw attention and he prefers design over chaos. Suddenly, Sheck is shot with an arrow and Oliver jumps into the room and shoots two arrows at Laurel. The arrows are connected with a rope and hit the walls next to Laurels head, causing the rope to strangle her just enough so that she cannot use her scream. Suddenly, Cayden is powerless and confronted by his nemesis. However, he solves the problem by activating three T-Spheres but these as well are shot out of the air by Oliver.

CaydenThinks

Cayden thinks about how to deal with Bertinelli.

Surprised, Cayden states that Oliver learned some new tricks. However, Oliver then realizes that he has no connection to Felicity anymore. Gleefully, Cayden states that he has tricks as well - and also friends. At that word, Anatoly Knyazev enters the room with several armed mercenaries. Through another door, Ricardo Diaz arrives with even more henchmen and cuts Laurel free. Vigilante turns up as well - meaning that Oliver is severely outnumbered. Unable to fight this many enemies, Oliver flees by using a rope arrow. The mercenaries fire after him but Cayden stops them, claiming that this is not the time or place for Oliver Queen to die. After Oliver has fled, Ricardo remarks that for a smart guy, letting Oliver go was a dumb move.

Having meanwhile found out that Cayden is watching the Arrowcave through his hidden camera, Team Arrow makes preparations to trick him. After making a plan with Jerry Bertinelli, Oliver heads back to the Arrowcave where he, Diggle and Felicity stage a conversation in which they state that Bertinelli has called in a high-profile death squad in order to combat Cayden, also talking about where the group is located. Listening on on this, Cayden murmurs to Black Siren that now that Bertinelli has his army, he should mee Cayden's. He sends Ricardo Diaz with several mercenaries to deal with the situation.

CaydenGroup

Cayden with part of his team.

In their combined numbers, Cayden's associates are able to take down Bertinelli's henchmen and even overpower Oliver. After seeing that the battle is lost, Bertinelli tries to flee but is held back when Cayden and Sheck arrive and shoots his two henchmen. Cayden states that he is disappointed by Bertinelli and claims that this can now go two ways for him and his men. However, suddenly bombs that Oliver and Bertinelli planted earlier go off. This allows Oliver to escape with another rope arrow but Bertinelli is left behind. Losing all hope, Bertinelli tells Cayden to just take the freaking port but is executed by Ricardo Diaz nonetheless. Afterwards, Cayden tells to the corpse that Bertinelli ultimately made the right choice by handing over the port and that this is why he won't have Bertinelli's daughter killed.

After the battle, Cayden meets up with Vigilante and tells him that he is worried - having seen surveillance feed that implys that Dinah knows about Cayden and Vigilante working together. Vigilante tells Cayden not to worry as he knows exactly how to deal with Dinah.

Shutting Down the City

Using the virus he implanted in the internet vault, combined with his hacking skills, Cayden hacks into several electronical devises into the city, including cars, hospital equipment and elevators. By causing those to crash, Cayden causes several deaths in the city. One of the victims of Cayden's attack is SCPD captain Frank Pike. Even after news get out, Cayden keeps hacking electonical devices, even crashing a plane inside the city.

CaydenCityHall

Cayden confronts Oliver at City Hall.

Under the alias Ben Gale, Cayden enters City Hall where he enters Oliver Queen's office during the chaos. After Oliver sends his aidé away, Cayden claims that he will let Oliver make the usual threats in a minute but wants to inform him first that his colleagues are expecting to hear back from him in six minutes and if they don't get a response, they will detonate the thermobaric bomb. Angry, Oliver asks him what he wants and Cayden states that he already told him - he wants vengeance for his son. He claims that he cared for, loved and protected his son like Oliver does for the city. He reveals that the entire city's infrastructure is under his command now and that people will keep dying if Oliver does not transfer $10,000,000 into an offshore bank account; this night and every night until further notice.

Oliver is shocked and states that this will bankrupt the city and Cayden replies that he hopes it does. He explains to Oliver that he is not doing this for money but for seeing Oliver suffer. Oliver furiously spits at Cayden that he did not kill his son but Cayden counters that he did; the very day one year Oliver tried to kill a criminal. He missed his target and shot Cayden's son instead. Oliver wants to know why Cayden has not just outed him as the Green Arrow if he wants to hurt him, but Cayden replies that he heard that somebody else did that already - revealing that he has nothing to do with Oliver's exposure after all. As Cayden turns to leave, Oliver warns him that the city will not negotiate with terrorists but Cayden only replies that come nightfall, these words will sound hollow even to Oliver. After Cayden has left, Oliver realizes that he could not have killed Cayden's son because he was not even in Star City at that point.

CaydenConfrontsOliver

Cayden reveals that he wants Oliver to suffer.

Back in the Arrowcave, the team realizes that there is a reason for Cayden's attacks. He is shutting down all routes out of the cities and this is also why he took control of the port. In fact, there is only one way out left Cayden did not yet attack, a tunnel. Meanwhile, Dinah's team is informed by Vigilante that Cayden soon wants to attack a subway tunnel by causing two subways to collide. They manage to foil this plan. In the other tunnel, however, Cayden causes a gas pipe to detonate, causing explosions in the entire tunnel. Although Team Arrow arrives to save civillians, the exit is effectively shut - trapping all inhabitants of Star City inside the city.

To prevent Cayden from killing more people, Oliver goes live and reveals to the city that a hacker called Cayden James can kill with every electronical device in Star City. He also reveals that Cayden made demands but strongly states that the city will not negotiate with terrorists. He reveals that safe zones have been erected in the entire city and tells the people that they will be safe there. Addressing Cayden directly, Oliver says that the city has survived far worse dangers than Cayden James. Watching the broadcast, Cayden amusedly tells Sheck and Vigilante that Oliver is so predictable that it almost takes the fun out of it. He tells the two that they will advance to the next step.

Blackmailing the city

Cayden sends Sheck and Vigilante with several henchmen to attack one of the safe zones. Before they can strike, Vigilante warns Dinah's team about it who in turn alerts Team Arrow. During the resulting fight, Vigilante actually kills Sheck in order to save Rene. After the attack has failed, Cayden shuts down all communications in Star City, including emails, phones and the internet. Ultimately, Oliver decides and orders that the money is wired to Cayden James. apparently giving in to the hacker's demands.

CaydenBetrayed-0

Cayden thinks about a possible traitor.

To combat Cayden's influence in Star City, Oliver plans for an A.R.G.U.S. team to be brought into the city. As Cayden monitors every airport, street or train track, and is in control of the port - killing everybody about to enter or leave the city, Oliver has the team brought in through the shoreline. As the divers emerge from the water, however, they are all electrocuted and killed when Cayden hacks their communication devices. In the following six days, Oliver keeps wiring money to Cayden, costing the city a collective amount of $70,000,000. Fearing that the worst can be expected, Oliver takes into account that they might have to evacuate the citizens into bomb shelters - although not everybody will survive in this case. In addition, supplys are running low in Star City and the population grows desperate.

In the meantime, Cayden calls in all his colleagues except Laurel for a meeting. After the last man, Vigilante, has arrived, Cayden states that the meeting is supposed to be a wake for their deceased colleague, Sheck. Vigilante soon realizes that Cayden suspects something and Cayden all but confirms it when he claims that it was unexpected that Oliver knew of their attack on the safezone. Cayden claims that he does not like surprises, but what he likes even less is the feeling that he cannot trust his comrades. Vigilante states that it seems that it is only him that Cayden does not trust but Cayden replies that if he were sure that Vigilante betrayed them, Vigilante would not be breathing anymore.

CaydenSuspicious

Cayden is suspicious of Vigilante.

The same day, Vigilante teams up with both Oliver's and Dinah's team and infiltrates Cayden's headquarter to steal information from Cayden's flashdrive. However, while he is doing so Cayden enters the room. Surprised, Cayden asks how Vigilante got it because all his colleagues have their respective domains and IT is not one of Sobel's - ergo he would not have a passcode for the door. Vigilante claims that this is true but reveals that Sheck had a passcode and was a little more loose-lipped than Cayden would like. Cayden says that this still does not explain what Vincent is doing in his server room. Using IT knowledge that Felicity is giving him, Vincent tries to save his hide by telling him that he was just impressed with Cayden's set-up and wanted to take a closer look. Cayden remains silent for a while and then seemingly accepts Sobel's explanation. Leaving the server room, Cayden tells Vincent to join him in five minutes as one of his associates has returned from the port with information.

However, Vincent plans to return to Helix instead. As he leaves the building, he is stopped by Cayden who tells him that he needs Vigilante for a rather important task. When Vincent asks what it is, he is suddenly tazered by Anatoly Knyazev and Cayden states that the task is "Rooting out a traitor". He has Diaz and Knyazev bring the unconscious Vigilante back into the building where he has him tied up. When Vigilante regains consciousness, Cayden claims that Vincent was always the enigma in the group - the vigilante who was willing to cooperate with criminals in order to defeat other vigilantes. Off-hand, James replies that he never really bought into Vincent, giving his former job as an undercover policeman. He then leaves Anatoly and Diaz to torture Vincent in order to find out whether he really is the traitor, claiming that even if Vigilante is hard to kill, he cannot withstand torture forever.

CaydenVigilanteDeath-0

Cayden approaches the wounded Vigilante.

During Vigilante's interrogation Cayden activates Vigilante's com, causing Team Arrow to believe that it was Vigilante himself who did it. They set out to save Vincent and apprehend Cayden James and his bomb, unaware that they are walking into a trap. Although Dinah is able to team up with Vincent, Cayden suddenly activates explosives which bury both of them under debris. At th same time, he has Diaz and Anatoly bring the thermobaric bomb to another of his facilities. Together with their truck, several other trucks leave the compound as well so that Oliver will not know which truck holds the actual bomb.

Seeing that Dinah is trapped under debris, Vince moves to help her. However, Cayden James and Black Siren appear. With a scream from Black Siren, Vince is blasted backwards and impaled on a metal pipe. Cayden moves closer, claiming that Vince's ability to withstand pain and mortal wounds is impressive. He goes on, claiming that everybody has his limits and ordering Black Siren to find Vince's. When she hesitates, Cayden tells her not to make him question her own loyalty as well. With Dinah unable to stop them, Black Siren screams at Vince until even his meta-human powers are unable to save him. After Vigilante's death, Cayden walks out of the room without another word.

CaydenWarnsHisTeam

Cayden thanks his colleagues for their help.

Back at their Arrowcave, the team obtains the evidence that was sent to Cayden to prove that the Green Arrow murdered his son from the files Vince stole from Cayden's server. They know that Oliver was not even in the city so the tape must obviously be fabricated. In addition, it seems that the tape was made by whoever also released the photo framing Oliver as the Green Arrow. The team realizes that there must be another traitor in Cayden's team - somebody who is playing both Cayden and Oliver.

With information they obtained from Vigilante, Oliver and Diggle head into another of Cayden's hideouts but find it completely abandoned. Suddenly, monitors start flackering and the two look at live video footage of Cayden James. Cayden reveals that he abandoned the base after he realized of Sobel's treason and that Oliver's allignment with Sobel caused him to think that he and Oliver no longer had an agreement. Oliver interrupts Cayden and tells him that there is something he needs to know, stating that they almost have proof that Oliver did not kill Cayden's son, but Cayden brushes it off as a desperate gamble. Oliver asks for more time but Cayden claims that time is something he and the city have run out of - he will launch the thermobaric bomb at midnight. Before ending the call, Cayden says that his son will find justice in the ashes of Star City.

CaydenStopped

Oliver stops Cayden's car.

Cayden then heads back into his new makeshift lair where he meets with the remaining team. He tells them that Arclight is in full procedure and that it is now time for them to end their partnership. When Anatoly asks how they will get out of the city before it is destroyed, Cayden tells them that they will be air-lifted out of Star City before it is destroyed and that respective share in the blackmail money will be wired into offshore accounts after they all have successfully escaped the city. Cayden thanks each of them for helping him in his project - stressing the importance Arclight means to him. As the cabal disbands, a touched Cayden once more thanks all of them in helping him getting justice for his son.

In order to avoid the explosion, Cayden leaves the city via car. Although Team Arrow can locate him, Cayden is too far away to reach him in time. However, with assistance from the Flash, Oliver and Diggle are transported to the street Cayden is currently driving on right before he can leave the city territory. When Cayden sees them in front of him, he stops his car and leaves it in mild amusement. He tells Oliver that Oliver could not have found a better way to make the bomb go off before midnight than taking Cayden into police custody. However, Oliver makes no attempt to do so and instead hands Cayden a tablet.

Learning the Truth

CaydenLearnsTruth

Cayden learns the truth about his son's death.

Cayden asks whether this is the "truth" Oliver mentioned earlier. When he sees that the tablet contains video footage of his son's death, he shuts it off and disgustedly claims that he will not watch that scene again. However, Oliver urges him to watch the entire video as it will be the first time Cayden sees what really happened to his son. While Cayden watches the video which shows that his son is not a bystander but the real target of an assassin who shoots him with an arrow, Cayden is horrified to realize that he was wrong all the time. He hectically runs some analytics in order to make sure the evidence is not faked and realizes that the video he was sent - causing him to believe that Oliver murdered Owen - was indeed manipulated. He also realizes that the meta-data on the video file confirms the video to be fabricated by the same person who faked the image of Oliver being the Green Arrow and that his person must come from within his organization.

Shocked, horrified and aghast, Cayden states that he wants to talk to his former colleagues. He orders Oliver to bring Diaz, Anatoly and Laurel to him alive, otherwise he will launch the bomb anyways. As Cayden walks back to his car, the outraged Oliver tells him that he will not round up Cayden's former partners in order to have them executed. Cayden replies that he only wants a pointed conversation but stresses the fact that he still has the bomb and would be perfectly fine with blowing up the entire city along with whoever killed his son. As Oliver has no choice but to comply, Team Arrow starts hunting for Cayden's former partners while Cayden drives back into the city.

CaydenDemandsTruth

Cayden demands the truth.

While the three are being captured by Oliver and his team, Cayden heads to where he has stored the bomb. After Black Siren has been captured, Oliver calls Cayden and asks him where to bring her but Cayden tells him that he will only reveal the location after Oliver has captured the entire trio. After ending the call, Cayden turns to the thermobaric bomb and emotionally vows that judgement will be passed for Owen.

After all three have been captured, Cayden is called again and this time, he gives Team Arrow the location of his bomb - an abandoned theatre. Unbeknownst to Oliver, his son William also overhears the call and heads to the theatre as well. When Oliver and Diggle arrive at the theatre with Anatoly, Cayden wants to know where Laurel and Diaz are. Oliver promises him that they will be there soon and Cayden then notices William and dryly tells Oliver that he does not remember having invited Oliver's son. Noticing how frightened William is, Cayden calls out the beautiful symmetry of the situation starting with his son and ending with Oliver's. Cayden then speaks to William in a friendly manner, welcoming him and introducing himself. He explains to William that he set things in motion because of his own son and when William asks where Cayden's son is, Cayden explains that he passed away. Moments before Dinah and Quentin arrive with Black Siren, Cayden says to Oliver that William is as brave and foolish as his father.

As the last to arrive, Diaz is led into the hall by Rene and Curtis. He directly speaks to Cayden, stating that his capturers told him that Cayden believes one of his former comrades killed his son. Cayden replies that he knows it and even when Anatoly is insulted that Cayden would trust people in masks over people he does business with and Diaz agrees with him, Cayden remains stubborn.

CaydenLosesIt

Cayden is ready to kill everybody in the city.

He reveals that he does not trust people as much as data and he has ample evidence that one of his comrades betrayed him. He addresses all of the people in the room and slowly breaks down, claiming that none of them lost a son and knows what that is like. While he slowly dives into his pain and hate, he then manages to snap back and remind himself that he did not lost a son; his son was taken from him. Diaz interrupts him, claiming that Cayden's grief has caused him to lose his grip on reality, Cayden pulls out the detonator for the bomb and challengingy asks Diaz what if it has.

Black Siren then speaks up, admitting that it was her who killed Owen. She also provokes Cayden, claiming that she enjoyed murdering his "stupid kid". Cayden slowly moves up to Black Siren and slaps her in the face. However, what he does not realize is that the detonator in his hand is interferring with the power dampening collar Black Siren is wearing. Black SIren provocatively asks Cayden if he doesn't want to ask her why she killed Owen but Cayden replies that he actually does not; he knows that she is lying. He reminds her that she hesitated to kill Vigilante and states that she would not have had the stomach to kill his innocent son. Suddenly, Black Siren realizes that her collar is malfunctioning and uses the opportunity to unleash a sonic scream that blasts everybody, including Cayden, off their feet. When he sees Cayden lying on the ground motionless, William attempts to take the detonator but Cayden suddenly jumps up and takes the trigger himself.

CaydenTakenDown

Cayden is defeated and apprehended by Oliver.

Seeing the insane look in Cayden's eyes, Oliver tells William to back away from him. He tries to calm Cayden by telling him that his son would not want this death and destruction but Cayden reminds him that his son's killer is in the vicinity and that he is perfectly willing to drag him down to hell with him. Realizing that Cayden is lost, Oliver embraces his son in what he believes to be his last moments with him. However, the sight of Oliver with his son reminds Cayden of his own son. He apologetically tries to explain to William why he is doing what he is doing but slowly breaks down again, muttering that he had the obligation to protect his own son and failed utterly. Stating that all this time, the person responsible for his son's death was Cayden himself, Cayden lowers the trigger and Oliver immediately hurls an arrow into his arm, causing Cayden to drop the trigger. Taking another arrow, Oliver aims it at Cayden's throat and threatingly dares him to make a single move.

Betrayed Once More

CaydenArrestedFinal-0

Cayden recognizes Diaz.

Cayden is arrested by the SCPD. Awaiting transfer, he is held in one of their interrogation rooms but is utterly broken and delusional. In the room, he is visited by Oliver but says with disinterest that Oliver's visit has been predictable. Oliver replies that he needed to look Cayden in the eyes and know that this surrender is not part of a bigger plan. Cayden replies that Oliver saved Cayden from doing the unspeakable and states that Owen would have been ashamed of him. He hands Oliver a document containing information about Cayden's cabal as well as the number of the bank account in which he stored the money he extorted from the city. As Oliver turns to leave, Cayden asks for something in return - he wants to visit his son's grave. Oliver promises him that he will make arrangements and then leaves the room.

Hours later, Cayden notices the surveillance camera in the room being turned off but is still surprised when Ricardo Diaz enters. While Diaz sits down in the chair opposed to Cayden, he tells his former comrade that while he expected this situation to play out in a lot of ways, he certainly did not expect it to go down like this.

CaydenKilled

Diaz kills Cayden.

Cayden sarcastically asks whether it would be foolish to assume that Diaz has come to rescue him and Diaz nods, gleefully mocking Cayden for always believing to be the smartest person in the room whereas it now turns out that he was not so smart after all. He then tells Cayden that he used Cayden's crusade against the Green Arrow to make moves on his own which have now resulted in Oliver Queen being under indictment, his team being fractured and the city in such a chaotic state that it is ripe for a takeover. Diaz claims that while Cayden only wanted to destroy the city, Diaz' plan was to take it over all along. As reality sets in for Cayden, Diaz reveals that he is in charge of the police captain as well as other city officials. Diaz stands up and claims that Arclight was really helpful for him to thin the herd. While Cayden realizes that his death is imminent and states that he assumes that Diaz is not done yet thinning the her, Diaz steps behind Cayden and rams a knife into his neck. As Cayden suffocates on his own blood, Diaz admits to him that it was him who had Cayden's son killed and tells Cayden to pass on his greetings to Owen when he sees him.

After Cayden's death, Diaz' police chief informs Oliver Queen that James was killed by an inmate during his transfer to Iron Heights penitentiary. In addition, the city is still in danger of financial collapse because Laurel Lance took the money Cayden extorted before Oliver could get it.

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