Cayden James

"I was hurt, truly! Not the betrayal so much as the naïveté of someone I thought had potential. I'm sorry, Miss Smoak... I'm afraid you're whats known as collateral damage! Horrible waste of talent..."

- Cayden James reveals himself

"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. 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.

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 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 a henchman 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. 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 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. 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.