If he thought of it, he might!

Dean overlooks some details like this, and Sam probably wouldn’t make it a point to bring it up past complaints when Dean fills his inside pockets and he ends up spending time with extra salt rounds or some emergency floss (you never know when you might need to stitch yourself up with it, Sammy!). They’re used to roughing it on both sides. 

Sam usually prefers a shoulder perch, so that’s at least clear of debris.