Generally any white collar criminal does not need to go to "big boy jail," and I'm not sure why that needs to be a thing. Is this like joking about prison rape, where we just assume that the consequences of being incarcerated aren't enough, and we need "Bubba" to add a little "extra" because we're not as civilized as we believe we are?

Either way, rest assured that in the real world, a hypothetical executive who was convicted of ordering a hit would end up being treated the exact same way as a mafioso who did the same.