Ah, I love threads like this !
JUDAS SIGHED is many things, but most importantly to me - it implies that even Judas Iscariot would pity the protagonist. I wanted the title to evoke deep regret and disappointment. On another level, it's meant to pair with the phrase "Jesus wept."
The tree on the cover of the comic is meant to be a Judas Tree. Myth claims that once Iscariot used the tree to end his life, the flowers turned from white to red/pink. It felt right to use the tree to hang a swing from - tree swings feel like such major symbols of childhood (more specifically, carefree life) that it kind of sums up what the conflict is.
One of my hopes in choosing the title was putting as much of the story on the tin as possible. I didn't want people to pick it up thinking that it would be some fun fantasy romp. Judas Iscariot is a pretty huge character (so to speak) in the Western consciousness, so I felt safe using his name in the title. The names Jude and Judas still have some pretty wicked stigma where I'm from, almost crossing into shorthand for a traitor.