It wouldn't help. $5 wrench would always know the exact sum you possess. He doesn't come at random and blindfold. If you deal with the excessive amount of crypto all your data are already in databases of the various 3-letters agencies and it is only the matter of time when they will be at the hand of $5 wrench.
If we're dealing with this level of preparedness, then it's no longer a "$5 wrench" - it's a $5 wrench + you fucking up your privacy willingly + you fucking up your digital/analog identity connections + you dealing with a persistent mugging.
If we're at the point where the guy is ready to start torturing you for every last one of your keys, odds are you're not going to survive, whether you give it to them or not.