In the earliest seasons of “Buffy,” Jonathan (Danny Strong) was Sunnydale High’s resident nerd, picked on to the point where he almost attempted to end his life. Unfortunately, while Jonathan’s desire for acceptance was understandable, he didn’t always go about it the right way. First, in the Season 4 episode “Superstar,” he uses magic to make everyone believe he’s a hero, and then in Season 6, he’s a member of the Trio, along with Warren Mears (Adam Busch) and Andrew Wells (Tom Lenk), three outcasts from Buffy’s former high school who team up in an attempt to amass power and influence through supernatural means.
After managing to survive the Trio’s dissolution at the end of Season 6, Andrew and Jonathan flee to Mexico but are soon lured back to Sunnydale by the First Evil, who wants to use them to open a mystical seal in the basement of Sunnydale High. Jonathan sees their actions as a means to their redemption, and he expresses his hope that they can alert Buffy to the presence of the seal and maybe even join her team. Instead, Andrew stabs him in order to use his blood to open the seal. Poor Jonathan never sees it coming, especially since Andrew is perhaps the one person in the world he trusts at that point. Adding insult to injury, because Jonathan is both small in stature and anemic, he doesn’t have enough blood in his body to fulfill the purpose Andrew kills him for.