Why do you not get the fact that it is irrelevant whether or not he chose to buy insurance if another party is liable for the damage? Your insurance is supposed to cover you for damage for which you are responsible, but if you're not responsible you (or your insurance company) can recover from the responsible party.
You keep harping on this insurance issue, but if the dog owner is responsible for the damage, it does not matter whether he chose to buy it.
What part of cheap skating don’t you get?
He saved all the C/C costs, spent it how ever he wanted and expects other policy holders to pay for his greed.