999,999 times out of a million, the answer is no.
the 1 time out of a million is when an attacker manages to intercept the hardware wallet being shipped to the victim and tamper with it.
That's not the hardware wallet being exploited though, it targets the user's computer. Verifying the address on the screen of a hardware wallet during confirmation would reveal the mismatch.
But most HW wallets have tiny screens that make users apathetic to validating tx data.
Probably not, he was storing his bitcoin private key on a low cost server, that regularly got hacked, as recently as a month ago. And he kept using it.