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Penn’s practice focuses on federal, state, local and international taxation matters, with emphasis on business transactions and planning, tax controversy work and tax-exempt organizations. He has extensive experience in acquisitions and divestitures, corporate restructurings, joint ventures, financings and international investments, including transactions in the financial services, energy, publishing, aggregates, healthcare, real estate, life sciences, media, telecommunications, specialty food and specialty chemicals industries. He also handles transactions involving historic, alternative energy and low-income housing tax credits, state & local economic development incentives and compliance issues. His corporate counsel experience includes projects in governance, compensation & benefits, risk management and government relations.

Penn routinely handles tax controversy matters before administrative agencies and judicial tribunals, including favorable resolution of numerous tax audits of income, estate, personal property, real property, business license and sales and use tax disputes. He also provides legislative representation before the Virginia General Assembly, the United States Congress and local governing bodies, including successful advocacy of tax incentives for companies expanding their operations in Virginia and numerous sales and property tax exemption matters.

In his representation of tax-exempt organizations, Penn counsels numerous entities on organizational and operational issues. His non-profit clients have included a statewide historic preservation organization, a preschool, a private secondary school, an educational foundation, a nonpartisan political advocacy group and a web-based campaign finance information provider.


Fellow, Virginia Law Foundation

Best Lawyers in America® for Tax Law and Litigation & Controversy - Tax Law, 2006–2024

Selected as "Lawyer of the Year" for Tax Law, Richmond, Best Lawyers in America, 2022

Recognized as a "Virginia Super Lawyer," Tax Law, 2006–2022; Top 50 Virginia Super Lawyers, 2010 - 2011, Top 100 "Virginia Super Lawyers," 2012

Selected as "Lawyer of the Year," for Litigation & Controversy - Tax Law, Best Lawyers in America, 2013, 2016 and 2019

Recognized as a "Top Rated Lawyer in Mergers and Acquisitions" by Corporate Counsel and The American Lawyer magazines, 2013

Listed by Virginia Business magazine as one of Virginia’s “Legal Elite” in Taxes/Estates/Trusts, 2020-2022

Fellow, American Bar Foundation

AV Rating, Martindale

  • 2019 "Best Law Firms" Badge Artwork
  • American Bar Foundation Fellows
  • Best Law firms 2021
  • Best Law Firms 2022
  • Best Law Firms 2023
  • Super Lawyers 2021
  • Virginia Legal Elite




Professional Affiliations

  • American Bar Association Section on Taxation: State & Local Tax Committee, Capital Recovery & Leasing Committee
  • Virginia State Bar: Tax Section, Chair 2001–2003
  • Virginia Bar Association: Tax Section, Council Member, 2005–present
  • District of Columbia Bar Association,Tax Section
  • Private Business Study Group, Richmond, Virginia, Convenor, 2009–2010
  • National Association of Property Tax Attorneys (NAPTA), Virginia Member  

Civic Organizations and Involvement

  • Founding Trustee, St. Mary’s Episcopal School, Richmond, Virginia, 2000–2006; 2009–2013
  • Trustee, The University of the South, Sewanee, Tennessee, 1991–1994, 2004–2007
  • Vestry, Treasurer & Finance Committee Chair, St. Mary’s Episcopal Church, Richmond, Virginia, 1999–2003
  • Leadership Metro Richmond, Class of 2002
  • Director, The READ Center, Richmond, Virginia, 1998–2001
  • President, Associated Alumni, The University of the South, 1991–1993
  • Ethics Commission, City of Annapolis, Maryland,1983–1988

New York University School of Law, LL.M., Taxation

St. John's University School of Law, J.D.

The University of the South, B.A., English, cum laude

  • Virginia
  • Maryland
  • District of Columbia
  • New York
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