- For the second version of The Trickster, see Axel Walker.
- "You have to admit, that was one hell of a trick "
- —James Jesse after being freed[src]
Rise to prominence as The Trickster
Around five years later, James Jesse took on the guise of The Trickster, wearing a unitard as a costume. He performed a series of terrorist attacks, killing at least 10 civilians and 2 police officers. Eventually, he was caught by police and incarcerated in Iron Heights Prison.
Re-emergence of The Trickster
Sometime before 2005, Jesse began talking to his son, Axel, through letters, grooming him to be an ideal comrade to him as The Trickster. For the next 10 years, they continue to talk and became close. In 2010, a criminal psychologist began talking to James. Before long, he was able to talk her in to committing suicide. As a result, Warden Wolfe had a cell specially-built for James Jesse. At some point in his incarceration, Jesse was given cable so he'd stop killing the guards, referencing the show Breaking Bad and the movie Speed in the future.
Five years later, after Axel had begun to act as a new version of The Trickster, Detective Joe West and Barry Allen came to him for help, giving him red liquorice to co-operate. He angrily claimed to have no association with the new Trickster, demanding that they kill him before he ruin his reputation. Apparently realizing that there could only be one way for the new Trickster to replicate the composition of his explosives, he directed them to his old lair. They returned later, having found nothing in his lair's vault. In discovering this, Jesse let them know of a giant bomb that he had, one big enough to blow up Central City. At the same time, they were notified of a vlog posted by The Trickster, claiming to have the giant bomb and would blow it up if they couldn't find him, searching between certain streets. As the police and The Flash began searching for it, Axel started to help James escape, as there had been no real bomb. With them, they took Henry Allen due to his connection to the Central City Police Department. While waiting around, Axel wondered why he'd been chosen, and James finally revealed that he was his father. That night, they began work on Jesse's big plan.
At an event held by Mayor Anthony Bellows at City Hall, they acted as waiters, poisoning the wine with one that took around an hour to act. Revealing themselves, they held the room hostage until they had transferred their bank accounts, at which time they would give them the antidote. The Flash soon found them and attempted to help, but Jesse placed a bomb on his wrist, hooked up to a speedometer disallowing him from going any slower than 600 mph. Barry was soon able to get it off and came back with an antidote, giving it to all of them. Realizing that he'd finally been caught, he gave up the location of Henry Allen. 
Nearing Christmas, Mark Mardon came to Iron Heights to free him and Leonard Snart, hoping the two of them would aid him in killing the Flash, however Snart declined. Jesse, on the hand, who had wanted to get revenge on the Flash ever since he was recaptured, agreed and sent out a video to Central City declaring his intention to kill the Flash. When Flash and Patty Spivot arrived at his location it was a trap and he attacked them with bombs. Flash escaped by shooting a whirlwind at the ground. Later Jesse dressed as Santa and was handing out bombs looking like presents to kids. Flash later caught Mardon but Jesse said that if he attacked him he would set off one hundred of his bombs, which Cisco Ramon, Harrison Wells, and Jay Garrick stoped with a powerful magnet. Mardon then attacked the Flash with ice balls because he refused to fight for fear of the bombs going off. After he was done with him, Mardon let Jesse kill him. Then Jesse saw the bombs exploding in the sky and the Flash tied him with Christmas lights. After Flash defeated Mardon, he and Patty Spivot took him and Jesse to jail.
Jesse is very possessive of his mantle, the Trickster, and was left enraged when Joe and Barry informed him when someone was using his mask. But despite this, Jesse and the new Trickster had something in common; they were both mentally-unhinged psychopaths who craved anarchy and death. Another difference is that despite his derangement, Jesse is a very intelligent man and in reality he was working together all along (who was actually his son) and helped him break out of Iron Heights. He is a skilled actor as well, able to fool a detective into thinking that he knew nothing about the new Trickster. He was quite manipulative as he was able to convince his therapist to commit suicide and sent Barry and Joe which was actually rigged with a bomb. Jesse proved to be a talented engineer as he was able to create a kinetic bomb that attempted to kill the Flash, but failed.
Despite this Jesse has a fondness for the Breaking Bad TV show and the movie Speed.
After being imprisoned yet again, he developed obsession with killing the Flash, as seen with the drawings he made of him.
- Skilled tactician: Despite his deranged nature, James lives up to his moniker, proving himself to be very crafty and methodical in his schemes. He is very patient and well-prepared, having used his time locked up in prison to plan out his escape while likewise preparing his next crime. He was also able to factor in the appearance of the Flash. Likewise, James has proven himself to be very manipulative and a skilled actor, faking ignorance and hatred for someone using his title.
- Expert engineer: Through his various terrorist attacks, James showed himself a very talented chemist and mechanic, able to produce a very unique and potent bomb-type. Only he was said to know the formula for the chemicals in his bombs, though Axel Walker learned it from him and used it in his own bombings. He is also able to design a very sophisticated bomb made especially for the Flash, which only failed to stop the speedster thanks to the assistance of Eobard Thawne teaching the Flash how to turn intangible.
- According to Jay Garrick, the Trickster doesn't have a counterpart on Earth-2.
Behind the scenes
- Photos of James Jesse when he was younger are taken from various episodes from the 1990 series, The Flash, in which Mark Hamill starred as the same character. In the episode, he also kidnaps Henry Allen, who's played by the actor that portrayed the original Flash, referencing the former rivalry.
- The name "James Jesse" is a play on American outlaw, Jesse James, as referenced by Joe West.
- In DC Comics, James Jesse was in actuality an alias assumed by Trickster, whose real name was Giovanni Giuseppe. It is currently unknown if "James Jesse" is also a stage name on The Flash television series.
- Jesse's line to Axel, "I am your father", is a reference to Mark Hamill's role as Luke Skywalker in the Star Wars films, in which Luke's father, Darth Vader, climactically reveals himself with the same words.
- James Jesse is an apparent fan of the television series Breaking Bad, as alluded to when he mentioned his master plan.
- In the Trickster's lair, the exploding door has a clown's face painted pretty similar to the Batman's archenemy, The Joker. Mark Hamill voiced The Joker in the 1990s Batman: The Animated Series, as well as later video games.
- The drawings in the Trickster's cell display The Flash donning the classic costume from the 1990 TV series rather than the current one.