Virginia Tax Review
When tax lawyers are shown to have been particularly "successful" in limiting or even eliminating their clients' tax liability, there is often an outcry, including for more law. But law's ability to deal with these problems is limited, for many reasons, including one less remarked upon than it should be: There is a continuum, from the "(Almost?) Over the Edge Envelope Pushing" tax lawyer to the "Old Venerable Risk-Hating" tax lawyer with, of course, most people falling somewhere along the continuum. Benefits to the "(Almost?) Over the Edge Envelope Pushing" lawyer might include living dangerously on the edge of detection, being more clever than her competitors in coming up with a brilliant shelter idea, being clever in avoiding detection, or the like. For the "Old Venerable RiskHating" lawyer, no such benefits would be available and the associated costs would loom large. Indeed, something that would be a cost to Venerable - say, appearing on the front page of the newspaper as somebody who had designed an aggressive shelter - might be a benefit to Envelope Pusher. Envelope Pushing is not always bad: the law doesn't always get things right. But it is certainly not always good. Regulatory interventions should be designed taking into account that different people approach tax compliance with different mindsets.
Claire Hill, Tax Lawyers are People Too, 26 Va. Tax Rev. 1065 (2007), available at https://scholarship.law.umn.edu/faculty_articles/65.