| “ | 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 villain in Arrow, appearing in the fifth season and returning as the main antagonist in the sixth season.
James 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 million people. As Cayden states to Oliver Queen, his motivation is that the Green Arrow cost him his son.
He is portrayed by Michael Emerson.
Biography
Past
Cayden James 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.
Eventually, A.R.G.U.S. showed interest in Cayden James. Considering him to be twenty times more dangerous than Edward Snowden, should he start to leak information, A.R.G.U.S. captured him and imprisoned him at a black site without a trial. He was kept imprisoned as a "person of interest" under order of Amanda Waller.
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.
It is revealed that his imprisonment strongly changed Cayden James and turned him into a bitter and cynical villain. Having learned about the battle on Lian Yu, James headed 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 million 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.
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.
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.
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
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.
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.
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 fourty-eight 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.
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.
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.
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