What I find strange about this whole thing is that you (OutOnaLimb) have your own insurance and you could easily file a claim and recover the money for your stolen property. Of coarse your premiums might rise, but your boss's premiums would rise if he filed the claim under his name (and that's assuming he's even covered for someone else's stolen property).
So paying the $1500 isn't even the issue, it's just an issue of maybe paying more premiums.
Most people are looking at this from the employees standpoint, but few are looking at it from the bosses standpoint. From my own experince, if I was your boss, I'd file the claim under my own insurance if I was covered, but that's just me. Over the years I've had to foot the bill for a number of things people working for me have broken including (1) A guy breaking a spring and tire on his own trailer for which I reinbursed him even though he was driving it (2) Another guy driving his skidsteer onto that same trailer about 2 years later and slashing a tire on some screws that were sticking out even though neither machine was mine and i was driving neither.
So basically what I'm saying before i ramble on forever is that people need to look out for their own equipment and never entrust it to someone else unless they are prepared to live with the consequences without reimursment.
Nobody I've worked for has ever reembursed me for anything I've lost or broken that belonged to me. I very rarely lend anything to anyone and I always make the effort to gather up my own stuff and lock it up in my own building or vehicle. That's probably why nothign has ever been stolen.