Some Bad Businessmen do go to jail. But what’s that like? I am yet to find an academic paper, or even a decent newspaper article, that discusses actual experience of executives in prison in an in-depth way. The Guardian makes do with pictures of business people who are, or have been, in prison. The issue I'm interested in here is the bite of punishment. Does prison hurt executives more or less than the ordinary man-of-crime?
The argument for prison hurting businessmen more is that they had more to lose in the first place. They can be disqualified from being the directors of companies, ruining their working life before they hear the cell door shut. Even if they are not disqualified, one must assume it’s far harder to get a high-powered position when you’ve done time. Further, the typical image of a businessman conjures up family life and community respect, both of which are liable to be broken by a stint in jail. Maybe just being branded a criminal - and it's associated shame and career damage - is punishment enough in their sphere of existence.
The counter argument could just run the way Sir Ken Macdonald put it on a (very interesting) BBC Radio show (now offline). On it, he said it was disgusting to argue that as richer people came from communities where family and reputation counted more, corporate criminals should be treated more leniently. But with respect, until studies are done, that’s not a ridiculous starting point. If prison is part-and-parcel of your community’s life, going inside is not the same culture shock as if it is really alien. Of course, you can say that if you have done something really bad, you deserve it, and elsewhere we will discuss the metrics of badness of white collar crime. But here, assuming Mr Businessman and Mr Carjacker have done equally bad things, maybe prison is a worse experience for Mr Businessman. This of course must be caveated - this general idea has to be applied on a case-by-case basis.
Other, more nuanced, complaints about the treatment of Bad Businessmen exist. Some include the idea that white collar criminals ‘get away’ with an easy life in open prisons, find it easier to conform with prison rules, and get more respect from staff than common-or-garden criminals. But then, conforming to rules should be rewarded, should it not? And, once in prison, it’s hard to see what danger is being posed by white collar criminals such that they should be in cells.
We come across scenarios all the time where wrongdoers’ means and backgrounds are considered in their punishments. Fines from the FA are set very high, because fining a footballer £200 is like fining me 2p. It might be unpalatable that to inflict equal punishment, white collar criminals should have more lenient sentences, but that is an indictment on social inequality, not a reason to punish in a de facto harsher way.