38 years ago - Giovanni Giuseppe is born to a family of circus acrobats.
28 years ago - 10-year-old Giovanni, exhibiting an genius level intellect but without any outlet, begins focusing his attention on building elaborate pranks.
23 years ago - 15-year-old Giovanni begins working as the con artist 'James Jesse', using his earning to find larger and larger pranks.
16 years ago - 22-year-old James, finally ready, unleashes a massive prank-based crimewave as the Trickster. He is stopped by the Flash.
13 years ago - 25-year-old James sides with Leonard Snart when he allies the Rogues with Barry Allen & Wally West to stop Eobard Thawne's takeover of the Rogues after he kills Lisa Snart & Sam Scudder.
11 years ago - 27-year-old James & the Rogues ally with Gorilla Grodd until his plans become evident. They then help Barry Allen & Wally West stop him.
7 years ago - 31-year-old James is caught & sent to prison by Wally West when he ends Barry Allen's ideal with the Rogues, holding them responsible for the fall of Frankie Kane.
5 years ago - 33-year-old James's clues scattered across the city lead Axel Walker to his trickster Lair, giving him a protege he's never met.
Characters like the Trickster are a little bit difficult to explain to people that aren't long-time comic fans. by almost every concieveable metric, it's a completely rediculous design. The character is a relic of an era when comics were a childrens medium. In this case, however, we have a very particular element that has managed to make him much more interesting. Before Mark Hamill ever voiced the Joker, he made an appearance on the 90's live-action Flash series as a brightly-colored rendition of the Trickster. Taken by itself, the appearance was just as rediculous as any other take on the character. Within a larger context, however; given Hamill's game-changing performance as the Joker, and the few times he's reprised his role as the Trickster, a version of the character takes shape that is way more than the sum of it's parts. This isn't the sort of development you could possibly plan, but it works surprisingly well.
James Jesse's Comic History
The Trickster first appeared in 1960, the creation of John Broome and Carmine Infantino. He's a conflux of a few different superhero tropes. Practical joke-themed villains are a comic book mainstay, dating well back into the golden age, and of course the character was created at the height of the popularity of brightly colored gimmick-villains that quickly populated the Flash's rogues gallery.
In later decades, when there was an effort to redesign many of the less-threatening villains created during the Silver Age, many of the Flash's Rogues started to experience stories that had them starting to reform. The Trickster in particular was actually depicted becoming a government agent. It was never the best fit for a brightly-colored character wearing anti-grav shoes, and for a while he was replaced by a new, younger version. Meanwhile, however, while all this was happening in the comics, the character was appearing in several other media, and a version of the character slowly evolved that manages to completely supersede his depiction in the comics. The thing that really did it. though, was the performance of a certain Tatooine farm-boy.
Mark Hamill's Trickster
Comic books often take their cues from outside sources when looking for ways to define characters that might not have quite found their stride within mainstream continuity, but you'd be hard pressed to find a character that has been so completely recreated by a single performance. Mark Hamil's role as the Trickster in the 90's live action series, his reprisal voicing the character in the animated Justice League series, and his return to the role in the new CW series has essentially completely rebuilt the character. While the comics have maintained a version of Jesse James that has reformed and joined the FBI... anything we do with the character is 100% defined by Mark Hamill.
Our James Jesse Story
In order to make Jesse James work we had to lean into the parts of his story that really establish him as a madcap trickster who is also inexpliciably a genius inventor. This is actually a fairly well-trot archetype in comics; characters like the c-list superman baddie the Prankster follow essentially the same MO. Even the Joker is a similar style villain, to a certian extent.
Thankfully, we have the Mark Hamill version of the character to build from. We can make him a person that is clearly a few chairs short of a dinette set, but who's dedication to madcap, crime-riddled pranks is an obessions all it's own, and a means to it's own end. This sort of insane energy works really well in the Rogues, and also does a good job establishing a legacy for a new Trickster, the far more dangerous Axel Walker.