Len Barclay's personal history is largely a mystery before he came to Odyssey, but it is clear that escapism was a major part of his life. Eventually, after a few months of hanging out with what they saw as a questionable group of friends, his parents, not knowing exactly what he was doing except that he had "changed" and begun to act even more secretively, convinced him to visit his cousins in Odyssey, in hopes that the town would be "healthy" for him.
During his visit, Len introduced Jimmy Barclay to a role-playing game called Castles & Cauldrons, which he had brought along with him. Jimmy was excited about the game, and played along even as Len (who would later insist on being referred to by his character's name) assigned him a character (as his own character's "apprentice") and railroaded him through a story of barbarians and evil wizards.
While Jimmy enjoyed playing the game, for the most part, he was put off by Len's unusual behavior, which included taking control of his character and telling strange stories about his friends back home, not about playing the game, but about "powers" which he and his friends believed the game could imbue its most devoted players with. He also somehow convinced the Barclays' cat to tear the arms off of Donna Barclay's doll and, overall, showed trouble separating the game from real life.
This culminated in his frustration over Jimmy somehow getting their characters ensnared by a group of wizards in the game, leading Len to decide that the only answer was to "summon" a character using a ritual — which involved at least one element that couldn't possibly have been legal — while ignoring Jimmy's protests, as usual, until John Avery Whittaker and Jimmy's father interrupted them. The fantasy seemed to abruptly fall away, as Whit stopped the "game" in progress.
Len returned home shortly thereafter. According to a phone call from his father, Len was last said to be going through counseling under a pastor who "knows about this kind of thing".
- Main article: Barclay family