If you haven't read George Packer's profile of Richard Holbrooke, Special Representative for Afghanistan and Pakistan, you should. (Sorry I can't link to the article, which is behind The New Yorker's firewall. Here's an abstract.) NPR's Renee Montagne interviewed him today, on Morning Edition.
On his blog, Interesting Times, Packer has posted a suggested reading list on Afghanistan and Pakistan. (Tom Ricks, whose blog I also read, often posts lists like this.) Packer recommends Steve Coll's Ghost Wars, Ahmed Rashid's Descent into Chaos, and Shuja Nawaz's Crossed Swords, among others.