Jim Gadwood has a diverse tax practice that spans many substantive areas, including federal tax accounting, transfer pricing, opportunity zones, the non-deductibility of fines and penalties, debt-versus-equity determinations, and earnings-stripping rules. He regularly assists clients with special industry tax issues, including insurance companies, investment funds, and investor-owned utilities. Jim has significant expertise representing taxpayers in connection with IRS examinations, conferences with the IRS Independent Office of Appeals, and requests for advance pricing agreements, changes in accounting method, technical advice memoranda, and private letter rulings. He is admitted to the U.S. Tax Court where he has docketed several cases.

Jim has received various rankings and recognition, including from Best Lawyers in America and Legal 500, where clients described Jim as a lawyer that combines "knowledge and ability with outstanding customer service and interpersonal, financial, business, and commercial skills." He has been named a "Rising Star" multiple times by both New York Super Lawyers and Washington, DC Super Lawyers.

In the transfer pricing space, Jim's representative matters have involved unilateral and bilateral advance pricing agreements, intercompany guarantee fees, and cost-sharing arrangements. He is currently working on an advance pricing agreement for a Global Top 10 company and negotiating one of the few multilateral advance pricing agreements under IRS consideration.

Jim's representative controversy matters include representing large corporations in IRS examinations, partnerships in TEFRA examinations, and high-net-worth individuals in audits conducted by the IRS Global High Wealth Industry Group. He has represented taxpayers before the IRS Independent Office of Appeals in the non-docketed, docketed, and early referral contexts. These controversy matters have covered a variety of substantive areas, including management fee waivers, extraterritorial income exclusions, transferee liability, debt-versus-equity determinations, and earnings-stripping rules. Jim has also written and presented on the new centralized partnership audit regime that will apply in future partnership examinations.

Jim is active in the American Bar Association Tax Section and the International Fiscal Association (IFA). He recently served as a co-General Reporter at the 2019 IFA Congress in London where he presented a major research paper on global implementation of limitations on interest deductibility following the BEPS Action 4 Report. He also regularly presents at tax conferences in the insurance, public utility, and oil and gas industries.

Federal Tax Audits 

  • Obtained a full IRS concession of a cross-border debt-equity issue involving several billion dollars of proposed tax, penalties, and interest. 
  • Prepared a multilateral advance pricing agreement request. 
  • Successfully resolved an IRS audit of a cross-border cost sharing arrangement. 
  • Reduced a proposed assessment relating to transferee liability by millions of dollars. 
  • Obtained an accounting method change regarding a taxpayer's LIFO accounting. 
  • Negotiated an IRS Appeals settlement of an audit involving a management fee waiver. 
  • Experience with Global High Wealth and estate and gift tax audits.

State and Local Tax Audits 

  • Reduced a proposed assessment of New York City General Corporation Tax by millions of dollars in an audit involving formulary apportionment. 
  • Experience with New York City Real Property Transfer Tax audits.


  • Used the docketed Appeals process to obtain a no-change stipulated decision in a Tax Court case involving IRS assertions of underreported income. 
  • Negotiated a multi-year settlement with the IRS after filing a motion for summary judgment in a Tax Court case involving the TEFRA statute of limitation. 
  • Obtained a complete victory in New York State Supreme Court on a motion for summary judgment involving a $200 million dispute over tax provisions in a contract between third parties. 
  • Experience with tax-related qui tam litigation under the New York False Claims Act.
  • The Best Lawyers in America®: Litigation and Controversy - Tax, 2020 - 2022
  • International Tax Review: Rising Stars Awards 2021 Americas, Transfer Pricing, 2021
  • Washington, DC Super Lawyers®: Rising Star, Tax, 2015 - 2016, 2018 - 2019
  • DC Bar Capital Pro Bono Honor Roll, 2018
  • Legal 500: Tax: U.S. Taxes: Contentious, 2016 - 2018, 2021
  • Legal 500: Tax: International Tax, 2017
  • New York Super Lawyers®: Rising Star, Tax, 2015 - 2016
  • Member, American Bar Association, Section of Taxation, Administrative Practice Committee 
Bar Admissions
  • District of Columbia
  • New York
  • Massachusetts (inactive)
Court Admissions
  • United States Tax Court
Speaking Engagement

Jim Gadwood and Alexander Zakupowsky will present "Tax Counsel's Report," at the EEI Virtual Taxation Committee Meeting on June 7, 2021.

Speaking Engagement

James Gadwood and Maria O'Toole Jones will present "Income Recognition under Section 451 and Section 162(f) after the TCJA," to the Tax Executives Institute's (TEI's) Carolinas Chapter on April 30,


The IRS's Large Business and International Division (LB&I) recently requested comments from large corporate taxpayers that rely on Revenue Procedure 94-69 to disclose potential tax adjustments

Tax Alert