Jeffrey G. Sherman (Chicago-Kent)
- A.B. 1968, Harvard
- J.D. 1972, Harvard
An English actor (possibly David Garrick) is said to have been visited on his deathbed by a friend, who complimented the actor on the calmness and gallantry with which he was facing his coming end. The actor replied, “Dying is easy. Farce is hard.” I think of those words as I sit down to write this profile: talking about myself is easy; writing about myself is hard.
I haven’t done much nonscholarly writing since my last year in law school, when I was the lyricist for the law school show, an original musical that the students presented each year. Our show concerned three law students who ran away from law school to join the circus. One of the songs I wrote was called, “One Ball.” It was about an incompetent juggler who could juggle only one ball at a time, and I can’t be blamed if you thought the song was about something else.
I graduated from law school intending to specialize in trusts and estates, thanks to the dazzling classroom performance of the late A. James Casner, who taught both property and estate planning. “I want to be just like him when I grow up,” I thought to myself. Estates law, with its ancient pedigree and its English associations, appealed to my antiquarianism and my passionate Anglophilia, so it seemed like the ideal specialty for me, and the strength of Casner’s intellectual commitment to the subject convinced me that a professional life might profitably be spent grappling with powers of appointment and fiduciary duties.
Life in private practice revealed what ought to have been clear to me back in law school: estate planning involves as much tax law as property law. Fortunately, I discovered that I loved tax law, too. Tax law was to me like an exquisitely complex machine that could be made to do all sorts of wonderful things if only one could find the right lever to pull or the right button to push. To find flexibility within an apparently rigid system was an almost intoxicating challenge.
When ERISA was enacted in 1974, I discovered that same challenge in employee benefits law, which had also become part of my practice. And a year later, I jumped at the chance to work in the United States Treasury Department, the Office of the Tax Legislative Counsel, laboring over new regulations that were to become the foundation of a new legal specialty. In ERISA, Congress effectively delegated to the Treasury Department the power to write a great deal of law, so being at Treasury at that time was like being present at the creation. I suppose I went there expecting to find a bunch of people exulting in their power, but instead I found people with a clear understanding of the limits of their authority and a fierce determination to stay within them.
From there, it was on to law school teaching, and I’ve been at it for more than a quarter of a century. I just love it. Nothing is more gratifying than seeing a student’s facial expression change from one of bafflement to one of comprehension because of something I’ve said or done. And despite my length of service and despite the number of times I’ve taught my courses, every year I continue to experience that oddly pleasurable embarrassment of having a student of mine correct some mistake I’ve made in class. In addition to teaching estates and trusts, gift and estate tax, and employee benefits law, I’ve begun teaching Law and Literature, which is about as far removed from tax law as one can get. It gives me a chance to revel in ambiguity instead of struggling to avoid it, and it gives me a chance to interact with students whom I might not otherwise see in my courses. Not everyone sees tax law as something exquisite.
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