Jim Gadwood is Counsel in the Tax Department. His practice focuses on federal civil tax controversies and other taxpayer interactions with the Internal Revenue Service. He has experience representing both corporate and individual taxpayers in matters involving federal, state, and local tax authorities. Mr. Gadwood has been described by clients in Legal 500 as a lawyer that combines "knowledge and ability with outstanding customer service and interpersonal, financial, business, and commercial skills."

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.

Litigation 

  • 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.
  • Legal 500: Tax: Contentious, 2016 - 2018
  • Legal 500: Tax: International Tax, 2017
  • Washington, DC Super Lawyers®: Rising Star, Tax, 2018
  • 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
Court Admissions
  • United States Tax Court
11.08.2018
Speaking Engagement

Maria O'Toole Jones, Mary Lou Soller, Jim Gadwood, and Nicholas Metcalf will speak at the 2018 Insurance Tax Conference, taking place November 8-9, 2018, in Rosemont, IL. 

Rosemont, IL