Update Jessie to Stretch results in unknown apt-key errors

It seems that error 139 indicates that the gpgv process died with a segmentation fault, much like you got when running sudo rm. Two such errors closely together isn’t encouraging. I have no clear evidence of what’s happening but my best guess is that some kind of filesystem corruption might have occurred that we’re realistically unlikely to be able to fix easily. I see that you have installed a great many packages on the Pi, including X and LibreOffice, so, if you do reinstall OSMC, it might be advisable to limit what you load onto a Pi.