If the club rates him so highly, they should be looking to offer Caleb a three year contract now, with guaranteed pay rises built in based on performance targets (appearances and goals). Start low, and build it up accordingly.
Who's to say we haven't?
Don't think he's ever gonna sign a pro deal with us tbh, his agent seems to be using social media tout he's already the complete player...which he's obviously not.
Obviously hope he signs a pro deal with us but if not then just fully utilise him next season on his youth contract.