Here's a suggestion. Take him to his bank and open a money market account with it. You can frame it as "here's a cushion for when you need it" or "to get you started on some savings" rather than "here's $1,000, you're poor so go buy some groceries and beer." Even if the latter is what he really needs he can withdrawal the money, close the account, and spend it as he pleases. But the way you frame the gift is important.
You're a good bro.
This. I was thinking a heartfelt, handwritten letter about strong suggestions of how to use the money. I agree 100% that he could use it as a foundation for savings, it would be my primary suggestion. I think I might wait to do all of this in person. I wont see him until after his bday, Im in Iraq right now.