Jonathan R. Black joined Caplin & Drysdale in 2019 as an Associate in the Tax Disputes & Tax Litigation and Complex Litigation practice groups. Prior to private practice, Mr. Black served for over five years as an attorney with the Office of Chief Counsel for the Internal Revenue Service, where he defended the IRS in Tax Court, drafted regulations and other published guidance, and advised the IRS and the Department of Justice on a myriad of legal issues. He also provided IRS attorneys training on administrative law and legal ethics. In addition to his near decade of experience in tax law and litigation, Mr. Black has prior careers in property development, procurement, and analytics.


Mr. Black advises individuals and businesses on a wide range of matters relating to compliance with their U.S. tax obligations, including:

  • audit assistance, IRS Independent Office of Appeals (“Appeals”) negotiation, and litigation;
  • information reporting obligations;

  • FBAR compliance;

  • penalties and reasonable cause; and

  • streamlined filing procedures and voluntary disclosure.


Mr. Black has negotiated full IRS concessions and abatements on matters including millions of dollars in penalties for failure to file foreign information reports (including Form 3520, Annual Return To Report Transactions With Foreign Trusts and Receipt of Certain Foreign Gifts, and Form 3520-A, Annual Information Return of Foreign Trust With a U.S. Owner) and various asserted income tax deficiencies.

Admissions & Education

Bar & Court Admissions
  • District of Columbia
  • New York
  • U.S. Tax Court

J.D., Cornell Law School, 2014

P.B.C., Minzu University, 2008

B.A., University of Oregon, 2005


Government Service

Attorney, Office of Chief Counsel, Internal Revenue Service, 2014-2019

Judicial Intern, Honorable Margaret M. Cangilos-Ruiz, U.S. Bankruptcy Court (N.D.N.Y), 2013

Newsroom & Publications

Speaking Engagements
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