A former competitive fencer, Jon focuses his practice on identifying cutting-edge solutions for clients moving forward in the post-tax reform landscape.
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.
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
News & Events
- Twelve IPB Attorneys Recognized by Best Lawyers | 08.19.2021
- Jon Holbrook Serves on DC Bar Taxation Panel | 05.27.2021
- IRS Clarifies Its View of Cryptocurrency Hard Forks | 04.14.2021
- Ivins Attorneys Teach Pro Bono Tax Class | 10.14.2020
- Jon Holbrook Offers Tax Advice to Entrepreneurs | 10.23.2019
- Code Section 162(m) Grandfathering Rule Under TCJA | 01.25.2019
- Code Section 162(m) Planning Strategies | 01.25.2019
- Employee Benefits Alert: New Disability Claims Rules | 03.23.2018
- IPB Attorneys Teach Tax Strategies for Artists | 02.05.2018
- EB Newsletter: Tax Reform | 11.17.2017
- IPB Tax, Trusts & Estates Newsletter | 06.23.2020
- IPB Tax, Trusts & Estates Newsletter | 02.2020
- IPB Tax, Trusts & Estates Newsletter | 10.2019
- IPB Alert: Notice 2019-09 and Section 4960 | 04.02.2019
- IPB Tax, Trusts & Estates Newsletter | 03.2019
- Affordable Care Act Update | 10.18.2018
- IPB Tax, Trusts & Estates Newsletter | 08.2018
- IPB Tax, Trust & Estates Newsletter | 03.2018
- Employee Benefits Update | 12.20.2017
- EB Update: Tax Reform | 11.17.2017
- IPB Tax, Trusts & Estates Newsletter | 11.2017
- "The Case for Custom Target-Date Funds" | 08.2017
Speeches & Presentations
- May 27, 2021: Jon Holbrook Serves on DC Bar Taxation Panel
- February 22, 2021: IPB Attorneys Offer Tax Strategy Presentation to Entrepreneurs
- February 4, 2021: IPB Attorneys Teach Tax Strategies for Media Professionals
- October 26, 2020: Corporate Tax Changes to Expect from a Biden Administration - Presentation to CPA Academy
- October 14, 2020: Ivins Attorneys Teach Pro Bono Tax Class
- May 15, 2020: Ben Grosz and Jon Holbrook Present on COVID-19 Tax Issues to Entrepreneurs
- October 23, 2019: Jon Holbrook Offers Tax Advice to Entrepreneurs
- April 11, 2019: IPB Attorneys Offer Tax Strategies to Entrepreneurs in Creative Fields
- March 28, 2019: Ben Grosz and Jon Holbrook Offer Tax Advice for Entrepreneurs
- May 16, 2019: Hybridity: Landmines in Your Org Chart? - Presentation to the TEI Baltimore Washington Chapter Conference
- May 9, 2019: Hybrids, BEPS and the TDCIA - Presentation to the International Fiscal Association, USA Branch, Westchester County, NY/Connecticut Region
- July 26, 2018: Jonathan Holbrook Spoke as Part of University of Florida Law Course on Recent U.S. Tax Reform
- March 27, 2018: Ben Grosz and Jon Holbrook Offer Tax Planning Insights to Small Business Owners at Pro Bono Program
- February 5, 2018: IPB Attorneys Teach Tax Strategies for Artists