Where by "some time in jail", you mean, "The rest of your life." Many people will make very expensive trades when facing long prison sentences, including peopl

Where by "some time in jail", you mean, "The rest of your life." Many people will make very expensive trades when facing long prison sentences, including people for whom a mafia torture and hit is a realistic possibility. So "being ok with it" hand-waves away a very large amount of duress.