Employment Litigation and Claim Settlements: Maximizing Tax Benefits and Avoiding Penalties
Tax Considerations for Employers When Negotiating Settlement Agreements; Drafting Strategies

Course Details
- smart_display Format
On-Demand
- signal_cellular_alt Difficulty Level
Intermediate
- work Practice Area
Employment and Workers Comp
- event Date
Thursday, January 16, 2025
- schedule Time
1:00 p.m. ET./10:00 a.m. PT
- timer Program Length
90 minutes
-
This 90-minute webinar is eligible in most states for 1.5 CLE credits.
This CLE course will provide employment counsel and tax advisers guidance for structuring complex settlements and complying with complex tax reporting and withholding requirements applicable to employment claims. The panel will discuss best practices for employers to structure settlements, maximize tax benefits, and avoid penalties when allocating settlement proceeds. The panel will also discuss the reporting of payments and the tax implications of plaintiff requests in settlement agreements.
Faculty

Mr. Fortuna is a partner in Greenspoon Marder’s Corporate & Business practice group. With over 30 years of legal experience, he concentrates his practice on domestic and international tax, business and estate planning, employee benefits, and executive compensation matters. Mr. Fortuna has substantial experience representing clients in the entertainment, higher education, clean energy, health care, hospitality, non-profit, manufacturing, retail, and real estate industries.

Mr. Wood handles a wide range of tax planning and tax controversy matters. He also serves as an expert witness on tax issues in legal disputes. Mr. Wood is best known for his expertise advising plaintiffs, defendants, and lawyers on the tax treatment of legal 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).

Ms. Cohen works with leaders across the professional spectrum, helping them navigate significant events in their career trajectory. Her breadth of knowledge and ability to consistently resolve matters successfully have made her one of the leading executive compensation and employee benefits attorneys in North America. Clients and attorneys seek Ms. Cohen’s practical advice and business-oriented approach to complex tax and employee benefits issues. She is known for deal-making and pragmatic problem-solving on private equity transactions, mergers and acquisitions, employment contract negotiations and development of incentive and deferred compensation strategies. Ms. Cohen is an Adjunct Professor of Law at New York University Law School, teaching Taxation of Employee Benefits in NYU's graduate tax program. In addition, she is a highly sought-after speaker and author.
Description
The law governing the approval of settlement agreements and the tax treatment of settlement payments is complex and continually evolving. Employment counsel and tax advisers negotiating settlement agreements for employers must understand how structuring a settlement, drafting a contract, allocating settlement proceeds, and making payments impact the employer's eligibility to claim tax deductions for the payments and related attorneys' fees.
There are also consequences for its obligations to pay payroll taxes, take withholdings, or file information returns for 1099 income. Improperly characterizing a settlement payment can result in tax liability, penalties, interest, or other unforeseen consequences.
To minimize potential adverse outcomes, employment counsel should carefully consider the settlement structure and the settlement agreement's language regarding taxable damages. Counsel should clearly state the purpose of all payments such as wages, damages, or attorneys' fees in the agreement, evaluate which payments are taxable and nontaxable, and identify the proper reporting forms for each type of claim.
Listen as our authoritative panel of employment and tax attorneys discusses the implications that employment counsel should consider and address when negotiating settlement agreements to resolve employment disputes.
Outline
- Settlement payments that must be reported
- Tax deductible settlement payments
- Settlement agreement structuring options
- Settlement agreement drafting strategies
Benefits
The panel will review these and other key issues:
- What types of options exist for structuring an employment settlement?
- What settlement payments are taxable as wage income to the recipient in an employment dispute?
- What types of settlement payments and related attorneys' fees are tax deductible by the employer?
- What tax reporting obligations do employers have following a settlement?
- What are best practices for anticipating and addressing tax issues when negotiating employment dispute settlement agreements?
Unlimited access to premium CLE courses:
- Annual access
- Available live and on-demand
- Best for attorneys and legal professionals
Unlimited access to premium CPE courses.:
- Annual access
- Available live and on-demand
- Best for CPAs and tax professionals
Unlimited access to premium CLE, CPE, Professional Skills and Practice-Ready courses.:
- Annual access
- Available live and on-demand
- Best for legal, accounting, and tax professionals
Related Courses

New EEOC Guidance on Employer DEI Initiatives: Prohibited Conduct, Limited Defenses, Policy Review and Development
Friday, May 23, 2025
1:00 p.m. ET./10:00 a.m. PT

FCRA Basics for New Attorneys: Employment Background Checks, Compliant Policies, Penalties
Monday, May 19, 2025
1:00 p.m. ET./10:00 a.m. PT
Recommended Resources
Making Continuing Education Work for You, Anytime, Anywhere
- Learning & Development
- Career Advancement