Silverstein founded (in 1959!) the Tax Management Portfolio series of practitioner guidebooks, which is why I got the notification, as I was the author for the passive loss rules volume in that series (for which he recruited me when I had just left the Joint Committee on Taxation and was starting my academic career at the University of Chicago). He also successfully cajoled me to write a few very short practitioner pieces for a tax practitioners’ real estate journal as the passive loss regs started coming out.
Each only took me a few hours to write, but their publication led to an amusing episode that I’ve always remembered. A former fellow tax associate at my pre-Joint Committee law firm, who had preceded me into academics, came across these pieces, at a point when my first academic writings had not yet appeared in print (and of course there was no SSRN yet). He evidently concluded that this must be how I was directing my writing efforts as a legal academic, which would have been horrifyingly naive and misguided, as the University of Chicago Law School would have rated their value towards my earning tenure at zero. I ran into this individual at a conference, and while, he was trying to be gracious, his excruciating politeness about the pieces, along with an involuntary smile that he couldn’t quite suppress, brought to mind a man talking to one whose pants have fallen down and doesn’t realize it. But I figured there was no need to tell him what I was actually doing from an academic standpoint; he’d find out soon enough. (Yes, we’re in an ego-driven and competitive profession, and he was certainly no worse than anyone else, including me.)
Anyway, back to Leonard Silverstein. While the 1986 Act was in process, lobbyists who had technical issues to raise with staff would talk to us at the JCT. He was very good, in the sense that he understood our perspective as people who wanted the provisions we were working on to make consistent sense internally and be workable. E.g., I recall his deftness in saying that his client had asked him to raise two issues, one of which lacked merit but he had to mention it before we moved on, and the second more substantial. He was right about their relative merits, and I understood how he was working me but in a way that I had to appreciate. (Plus, the issue he raised truly was meritorious, in absolute terms whether or not comparatively so to the rest of the landscape, as the provision at issue, relating to the disallowance of miscellaneous itemized deductions, was a bit sketchy to begin with, in that it could result in overmeasuring net income.)
I subsequently heard from someone else that he referred to a couple of us at JCT, with whom he was discussing these issues, as “the kids on the Hill,” which I found amusing – I was in my late 20s – but by no means offensive. There was something a bit peculiar about an eminent senior law firm partner in his mid-60s, no doubt accustomed to deferential treatment most of the time, having to plead his case before a couple of bright-eyed recent law school grads who were excited about being near the pulse of what was happening at that moment. We certainly met plenty of senior law firm partners who were clueless about the sorts of arguments we’d respect, had never been contradicted by anyone for several decades, and thought they give us orders as if we were grocery store clerks. But he seemed to me to have a bemused and tolerant, albeit perhaps slightly weary, sense about the peculiarity of the status reversal implicit in his having to plead with us, at his career stage, to agree with him.
I thus got to like Silverstein, while not forgetting that he had his job to do and I had mine. Maybe it was mutual, as I’m sure we bantered a bit about the merits of the issues that he raised, I think with some shared enjoyment. When he found out that I was leaving JCT, he asked me if I wanted to join his firm, and when I said I was going to U Chicago he brought up the Tax Management Portfolio, which paid me enough to be worth my while at the time.
I don’t recall seeing him in person after I left Washington in 1987, although while I was still in Chicago (through 1995), we discussed TMP follow-ups by phone. But I’ve always remembered him fondly, and he somehow conveyed to me a sense of being a substantial person even though we never discussed anything that wasn’t narrowly professional.