-snip-
This was back in 2010 when everything was non standard. He likely used cli tools to generate the key. Is it possible that they may be custom encoded?
There's a possibility of that since WIF isn't a thing back then, but most old tools exports the keys in 64 hex characters.
He should remember the tool that he have used to export or create those.
Or ask around for old tools that people may have used to export private keys from wallet.dat files before this
PR.
I don't know how to attach an image here.
Just upload it to
talkimg.com, then share the img BBCODE in your reply.
Do not screenshot the actual keys though.