Steal a Hireling

[snarky]

Andrew's answer seems the clearest in this regard:

Originally Posted by Andrew Hackard

Bob is correct. If you discard the Hireling, you lose anything he is carrying.

In any instance where the Hireling is DISCARDED, you lose what he is carrying.

And this quote from MM addresses when he's not discarded:

Originally Posted by MunchkinMan

Steal a Hireling would be a change in loyalty, so the Item goes with the Hireling.

If he is simply "changing loyalty" - eg: stolen by another player - then the item attached to him goes with him.

That's, at least, how we've always played it. Doesn't mean it's right, but it's a simple, bright-line rule.