How? Well, supposedly, you can pick his pocket for it before and after the quest he is involved in. I've already taken his ammunition (with a sneak skill of only 44) but even with a damn stealthboy I can't grab it from his warm, still-living hands!
So, do I still need to give him another weapon and ammunition for it? If I do, would a 9mm be enough? What the cheapest, easiest-to-find weapon (with the lowest DAM possible) that can be used?
Note: My companions were with me when I tried this, I was [HIDDEN], it was dark, I was using a stealthboy, and I attempted both when he was sitting on the tree stump and when he was sleeping.