Your friend might not have enough steem power to make a transfer. The Steem blockchain does not charge fees but you do need to have a minimum amount of vests aka "steem power" (I am not sure what the threshold is).
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He had a bunch of STEEM POWER and then powered down. Now he can't do shit. How is he supposed to gain STEEM POWER, if he can't even vote or be create posts?
What is the name of your friend's account?