26. Cayden James
We were teased with Cayden James before him actually showing up in season 6 and when he arrived, he brought with him a villainous group that was bound and determined to do what every they could to destroy Star City. Anyone who can bring an entire group of villains together deserves some credit for that.
This is a character with a solid backstory, plenty of charisma, and an actor who really delivered with every line and moment on the screen.
The fact that Cayden has been manipulated into believing that the Green Arrow was the person responsible for the death of his son certainly helps add to his bad guy ways and furthers many of his motivations. Unfortunately, by the time he learned the truth, it was too late for him in many ways.
Perhaps what makes Cayden James an interesting character is the fact that at one point he was actually an ally of Felicity Smoak’s and she was even a part of a group who helped to save him after he was imprisoned for hacking activities. The problem with his imprisonment was that it definitely did him no favors when it came to his sanity.
As someone who clearly viewed Team Arrow as an enemy, even when they were wrongly accused, Cayden James is the kind of bad guy who made an impact, even if there were plenty of times when he was more of the monologuing villain often made fun of when we watch other comic book related properties.