3 Paths to Tax Law

The paths that UVA Law alumni have taken to become tax lawyers vary, but they all have in common an alma mater that fosters a love for tax, with courses taught by experts seasoned in the field. Alumni have joined academia, launched firms focused on tax law, managed the taxes of corporations such as Exxon Mobil and Amazon, served in the U.S. Office of the Legislative Counsel, and held leadership positions at the IRS.

Meet three alums who continue the distinguished tradition of Law School representation in this area.

Hal Hicks ’85

Partner, Skadden, Arps, Slate, Meagher & Flom
Washington, D.C.

When did you decide to become a tax lawyer?

I went to law school to be a public defender with the goal of saving the world — I fell well short of that mark! I think I made the final switch away from being a public defender in my first semester, second year, when I took my first tax class. I realized then that being a tax lawyer would not be about crunching numbers or filling out tax returns. Instead, it was about complex analysis of facts and law — including statutes, regulations, case law and IRS rulings, etc. My parents had suggested back when I was in college that being a tax lawyer could be good because “there will always be tax law.” Moreover, my then-girlfriend and wife of almost 35 years gently mentioned that tax lawyer might provide a higher standard of living than being a public defender!

Did any of your UVA Law professors influence your decision to go into tax law? If so, who was it and how did they encourage or inspire you?

I had a wide range of tax professors at UVA that certainly affirmed the tax field as an interesting field of practice. These included Hank Gutman, who used the phrase for tax planning that “pigs get fat and hogs get slaughtered.” I still use this phrase often when discussing options with clients. Also, Bill McKee, Tom White, Saul Levmore and Julie Roin. And I could not forget the tax class I took with Mortimer Caplin (a future partner of mine) that really ramped up our enthusiasm for the dynamic nature of tax practice; he also resolved our concerns about tax practice becoming obsolete with the ongoing process of passing the 1986 Tax Act. Mort and Bill and Hank each also created a real desire in us for government service (as they each had) which helped lead me to run the international tax groups at IRS Chief Counsel and at Treasury.

Did any of your classmates at UVA Law join you in tax practice and have you remained in touch with them?

In law classes and on the Tax Review, I studied and worked on publications with many fellow students. Alveno Castilla, Sonny Talley and Peggy Israel, among many others, inspired me to pursue tax law as a profession. We have stayed in touch over the years.

What has been your experience with the Virginia Tax Study Group?

The Virginia Tax Study Group is an excellent tax conference. I am on the boards of several tax conferences and speak (pandemics aside) often. I have been privileged to be a panelist several times at VTSG and to have attended often. It has sometimes conflicted with a conference I help run in Europe, so I have missed some dates for VTSG, but I make it whenever I can. Mort Caplin and Eddie Cohen were huge supporters, so that conference means a great deal to me.

Select Publications

• “Select Cross-Border Tax Issues in Reverse Morris Trust Transactions,” Int’l Tax J., Nov-Dec 2017.
• “Select Corporate Migration and Combination Considerations in an Ever Changing Environment – Update,” Int’l Tax J., July-Aug 2014.

Amanda Leon ’17

Associate, Caplin & Drysdale
Washington, D.C.

When did you decide to become a tax lawyer? Did any of your UVA Law professors influence your decision to go into tax law? If so, who was it and how did they encourage or inspire you?

Hard as I tried, I just could not stay away from tax. Although my pre-law school resume might have fooled some (e.g., CPA and [Volunteer Income Tax Association] volunteer), I did not intend to become a tax lawyer. In fact, I arrived at UVA Law as a 1L announcing my retirement from tax (jokingly after an “illustrious” two-year career as a tax accountant) and very ready to try something new. I took Federal Income Tax that spring solely because my section’s Peer Advisors recommended it as a must-take before graduation, and I figured I might as well take it before I forgot everything I knew about tax. UVA Law and its amazing tax faculty, however, had other plans for me. Just a few weeks into my Federal Income Tax class I was out of retirement discussing the intricacies and logic, or lack thereof, of our tax system with Professor Ruth Mason; by the end of the semester, I was headed to spend my summer working at Caplin & Drysdale as a tax summer associate.

UVA Law’s tax course offerings, which much to my surprise — and gratefully so — were plentiful, solidified my decision to become a tax lawyer and, better yet, prepared me to become one. For example, classes like Professor George Yin’s tax policy seminar taught me to think critically about the why behind tax, Professor Andrew Hayashi’s international tax course taught me how to parse and apply the code, and Professor Mason’s EU tax and international moot court competition classes taught me how to write and advocate in the tax world. Most importantly, however, my time in the tax classroom revealed how passionate all of my professors are about their field and that I would never be bored as a tax lawyer. And here I am, a tax lawyer, much thanks to them.

Did any of your classmates at UVA Law join you in tax practice and have you remained in touch with them?

In addition to providing an invaluable foundation for my future practice (not to mention fostering my inner tax nerd!), UVA Law's vast offering of tax courses provided a unique opportunity to learn and work alongside familiar faces each semester, a mini tax bar of sorts, and make lifelong friendships along the way. While not all of us practice tax now, many of us do and I always look forward to seeing those familiar faces at Virginia Tax Study Group meetings and other conferences or reviving a group text thread when a big case is decided (or even breaking it down on the dance floor at our mutual friends' wedding). 

What has been your experience with the Virginia Tax Study Group?

I look forward to attending VTSG meetings every year — and I swear, not just because it is a great excuse to return to Charlottesville! VTSG seems to attract the best and the brightest tax professionals from academia, the government, and private practice year after year, which makes for fascinating panels and discussion. I always leave in awe of both how much I’ve learned and how much more I have to learn. On top of that, in my experience, the VTSG attendees have always been incredibly warm and welcoming to newcomers. I always enjoy catching up with those I’ve met in years past, as well as meeting new people.

Select Publications

• "Mining for Meaning: An Examination of the Legality of Property Rights in Space Resources," 104 Va. L. Rev. 497 (2018).
• "Reconsidering European Court of Justice Jurisprudence on Limitation on Benefits Clauses: Why the U.S. Should Care," 46 TM Int'l J. 83, Bloomberg BNA Tax Mgmt. Int’l J., February 10, 2017.

Len Teti ’05

Partner, Cravath, Swaine & Moore
New York

When did you decide to become a tax lawyer?

I enrolled at the Law School without any of the markers you might expect for a future tax lawyer: I had no significant exposure to finance, economics or accounting in my undergraduate education or my early work experience. It was in the spring of my 1L year that I took Federal Income Tax with Professor Paul Stephan. I found it interesting enough to sign up for International Tax the following fall as I was interviewing for 2L summer jobs. Interviewing with tax lawyers through that process and then working as a summer associate in the Tax Department at Cravath helped convince me that I wanted to work as a transactional tax lawyer. 

Did any of your UVA Law professors influence your decision to go into tax law? If so, who was it and how did they encourage or inspire you?

Yes, certainly. Professors Mitchell Kane (now at NYU) and Thomas White encouraged me to pursue a tax practice, and I spoke to them at some length about what to expect in the early part of my career. Both were very supportive and helped guide me as I started my first years in practice.

Did any of your classmates at UVA Law join you in tax practice and have you remained in touch with them?

Gavin White ’04 was a year ahead of me in law school and is now a tax partner at Skadden. He and I were in several tax classes together and remain in touch from time to time. Andrew Carlon ’07 was two years behind me and has been in the Cravath Tax Department with me for over a decade. He is one of our senior attorneys and an extremely valuable member of our team. 

What has been your experience with the Virginia Tax Study Group?

I try hard to attend these meetings every year. They are always worthwhile and draw a useful mix of practitioners, professors and government lawyers. 

Select Publications

• “Unanticipated Costs of Paycheck Protection Program Loans in M&A Transactions,” Harvard Law School Forum on Corporate Governance, June, 17, 2020.
• “US Government Finalizes Rules on Transfers to Partnerships with Related Foreign Partners,” European Tax Blog, February 10, 2020.
• “US Treasury Department Loosens ‘Earnings Stripping’ Rules,” European Tax Blog, November 4, 2019.
• “The World Turned Upside Down: Understanding Corporate Inversions,” Corporate Live Wire 2014 Expert Guide: Tax, September 2014.