Depending on how technology savvy you/your family is, you may need some help with this one.
1. Go to an electronics store and buy an external hard-drive like this one
. (Yes, I do recommend Wester Digital.)
2. Get a program that allows you to rip DVD content. There's probably a free one on the internet.
3. Rip all of the DVDs that will fit and put them on the external hard-drive.
4. Ship the hard-drive to your bother.
This is, of course, assuming that he has a computer with him and access to electricity. Seeing as how he isn't in Iraq, though, I would think that these are available to him. I have heard of other military families doing this, so I am under the impression that it is allowed.