Tax Treatment of Lawsuit Settlements: What Every Litigator Should Know

Robert W. Wood
Robert W. Wood | Wood LLP

Rob Wood is often listed among the top ten tax lawyers in America. He handles a broad range of tax planning and tax controversies. He also serves as an expert witness on tax matters in civil cases, class actions, disputes over independent contractor or employee classification, etc. A widely published author known for explaining and demystifying complex tax concepts, Mr. Wood is best known for his expertise in advising plaintiffs, defendants, lawyers, and settlement funds on settlements and judgments.

Live Video-Broadcast: June 18, 2025

1 hour CLE

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Program Summary

This program offers a timely and practical analysis of the tax implications related to lawsuit settlements and judgments. Attendees will gain a clear understanding of which types of damages are taxable, when settlement proceeds may qualify as capital gains, and how to navigate key distinctions under current tax law. The session will also explore the treatment and deductibility of attorney’s fees, including recent developments under the Tax Cuts and Jobs Act (TCJA). In addition, participants will learn best practices for drafting settlement agreements, negotiating favorable tax outcomes, and avoiding common pitfalls related to Form 1099 reporting.

Key topics to be discussed:

  • Understanding damage awards
  • Capital gains vs. ordinary income
  • Attorney fees and tax deductibility
  • Strategic settlement structuring

This course is co-sponsored with myLawCLE.

Date / Time: June 18, 2025

  • 1:00 pm – 2:00 pm Eastern
  • 12:00 pm – 1:00 pm Central
  • 11:00 am – 12:00 pm Mountain
  • 10:00 am – 11:00 am Pacific

Closed-captioning available

Speakers

Speaker_Robert W. Wood_MDBRobert W. Wood | Wood LLP

Rob Wood is often listed among the top ten tax lawyers in America. He handles a broad range of tax planning and tax controversies. He also serves as an expert witness on tax matters in civil cases, class actions, disputes over independent contractor or employee classification, etc. A widely published author known for explaining and demystifying complex tax concepts, Mr. Wood is best known for his expertise in advising plaintiffs, defendants, lawyers, and settlement funds on settlements and judgments. He authored the leading book on this topic, Taxation of Damage Awards & Settlement Payments (5th Ed 2021), as well as the Bloomberg Tax Management Portfolio Tax Aspects of Settlements and Judgments (522).

The author of numerous other tax books and hundreds of articles, he is listed among the elite tax lawyers in the United States by many best lawyer’s periodicals. Mr. Wood writes regular columns in Tax Notes, Forbes and other publications, and comments on tax matters in the media.

Agenda

I. Understanding damage awards| 1:00pm – 1:15pm

II. Capital gains vs. ordinary income | 1:15pm – 1:30pm

III. Attorney fees and tax deductibility | 1:30pm – 1:45pm

IV. Strategic settlement structuring | 1:45pm – 2:00pm

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