Jonathan L. Holbrook

Clients engage Jon throughout the income tax lifecycle for assistance in planning transactions, developing reporting positions, assessing refund opportunities, and defending positions in tax controversy scenarios.

Jon’s practice focuses on cutting-edge federal income tax issues facing businesses and individuals, as well as related employee benefit and executive compensation issues.

He supports accounting firms, law firms, entrepreneurs and multinational corporations with creative advice on complicated and high-stakes matters.  He advises on U.S. and international business operations in a wide range of industries, including financial services, manufacturing, crop sciences, pharmaceuticals, cryptocurrency, software and real estate.

Clients have sought Jon’s advice on issues including: controlled foreign corporations (CFCs), global intangible low-taxed income (GILTI), subpart F income, section 245A, the base erosion and anti-abuse tax (BEAT), the foreign-derived intangible income (FDII) deduction, section 1031 like-kind exchanges, section 168(k), FIRPTA, the section 199A (QBI) deduction, worker classification, the employee retention credit, and claim-of-right relief.  He also has significant experience with challenging IRS guidance.

Before joining the firm, Jon graduated magna cum laude from Harvard Law School, where he was a winner of the Williston Negotiation Competition and co-founded HLS Effective Altruism.  He also served on the General Board of the Harvard Civil Rights-Civil Liberties Law Review and was active in the school’s Federal Tax Clinic.

Practice Areas

Education

Harvard Law School, 2016, J.D., magna cum laude

Yale University, 2012, B.A., summa cum laude, Phi Beta Kappa

Bar & Court Admissions

District of Columbia

Maryland