I still don't get why would anyone hold their coins in a wallet that allows a finite attempts to log in.
Just keep your secret phrases and the fact you are playing around in the crypto field a secret.
You have to remember that this is way back, when bitcoin was still in its infancy and definitely those early bag holders security practice is nascent and probably this is one reason he uses a drive that has finite attempts.
If this happens in 2020, then obviously he could have bought a hardware wallet to put all his bitcoins and then write down the seed. So he is not that stupid, but probably lack the knowledge that time and chooses to hide everything in a usb drive.