Hmmm... Off-subject slightly, but I've been thinking about Li'l Cal.
My thinking is that he's not just a juju. Note that anytime a Cherub or the representation of a cherub got Tricksterized, they turned into Cal lookalikes. In essence, Cal is the image of a tricksterized Cherub.
Now, Hussie has stated that the Trickster power-up is effectively a trap. It's an attempt to shortcut personal growth by becoming stupidly powerful and plowing through/ignoring one's issues.
And as Sburb is itself all about personal growth - it could even be stated that personal growth is required in order to complete the game - Trickster mode is effectively a honey trap: It tempts you with all that power, but you cannot satisfactorily progress in the game while using it. So my guess is that Caliborn, hatching out of Li'l Cal, has effectively perma-trickstered himself. He's under the mother of all cheat codes.
And my second guess is that Caliborn never completed his session. His session is a dead session, the most difficult of all sessions, and Caliborn has been failing it at every turn. By killing Calliope he ruined his own cherubic maturation process, he's been trying to skip all the content, and he's made it clear he'd jump at the chance to Tricksterize himself. I'm fairly certain he's made it impossible to win his own session. In fact, I'd guess that the Troll and Kid sessions are all subsessions of Cal's - they are part of his own session working to bring him down now that he's fallen into its trap.
That's how I'm starting to read things. Lord English cannot win. Not because of narrative reasons or predestination, but simply because he's been continuously hosing himself over from day one.