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Courses/Law/Employment Law

Breaking Up Is Hard to Do: Settlements in Employment Cases

Master employment case settlements. Gain a deep understanding of tax implications, structured settlements, and negotiation strategies to maximize client outcomes and achieve finality.

Created byNYS Academy of Trial Lawyers
BeginnerUpdated Sep 24, 2025
Breaking Up Is Hard to Do: Settlements in Employment Cases

What You'll Learn

check_circleUnderstand tax implications in employment settlements.
check_circleLearn how structured settlements offer tax deferral.
check_circleIdentify benefits of non-qualified assignments.
check_circleExplore flexible structured settlement payment plans.
check_circleAnalyze above-the-line tax deductions in employment cases.
check_circleEvaluate lifetime payment options for plaintiffs.

About This Course

Here's the reformatted version:

Structured settlements offer powerful advantages in employment cases, yet their mechanics, tax implications, and strategic applications are often underutilized. This course provides a comprehensive overview of both traditional and nontraditional structured settlement approaches, with a focus on how they can be used to achieve income averaging, optimize tax outcomes, and create customized payment streams that meet the real financial needs of plaintiffs.

Drawing on a hypothetical gender discrimination case, the course walks through the full settlement process — from the inherent difficulties of resolving employment disputes to the practical application of annuities and funding agreements. Participants will leave with a working understanding of how to deploy structured settlements as a strategic tool that benefits both sides of the table.

Learning Objectives

By the end of this course, participants will be able to:

  1. Describe the inherent challenges in settling employment cases, including the role of personal animus and financial stakes in shaping negotiations.
  2. Compare traditional cash settlements with unfunded structured settlements, evaluating the pros, cons, and risks associated with each approach, including defendant creditworthiness.
  3. Explain the evolution of structured settlements and the critical role of the Periodic Payment Settlement Act of 1982, including the concepts of qualified and nonqualified assignments.
  4. Apply relevant tax considerations to employment case settlements, including the above-the-line deduction under IRC Sections 62(a)(20) and 62(e)(18) and the annuity rules under IRC Section 72.
  5. Structure attorneys' fees and design customized payment streams that provide guaranteed income, tax deferral, and long-term financial security for plaintiffs.
  6. Identify the role of structured settlement brokers in the settlement process, including their compensation model and the impact of anti-rebating laws

Your Instructors

NYS Academy of Trial Lawyers
NYS Academy of Trial Lawyers
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The NYS Academy of Trial Lawyers is the largest statewide trial bar in the US with 5,700+ lawyer and judge members. We are committed to protecting, preserving and enhancing the civil justice system. Our highly acclaimed CLE programming features extraordinary presenters covering the most timely and important topics.

Martin  Jacobson, Esq.
Martin Jacobson, Esq.

General Counsel at Creative Capital Inc.

Marty is a licensed NY and NJ trial lawyer with experience in both state and federal courts. For many years his concentration was primarily in employment discrimination cases. He’s a well-known lecturer and has presented numerous programs to the bench, bar association groups, and law firms. Marty and CCI’s legal team draft, review, and/or revise all of the legal documents needed in Structured Settlements and Periodic Judgments for attorney clients. Also an expert on the subject of Periodic Judgments (CPLR Articles 50-A and 50-B), Marty assists CCI’s attorney clients in obtaining better settlements for their clients.

Morris Lener
Morris Lener

Vice President at Creative Capital Inc.

Morris is NY State’s leading expert in assisting attorneys at mediation and settlement conferences in achieving better offers by employing the Multiplier Effect of CPLR Art. 50-A and 50-B. He has participated in hundreds of mediations throughout New York State. In the area of Wrongful Conviction and Imprisonment, Morris has handled some of the largest and most prominent cases in the nation.

Rhys  Andersen
Rhys Andersen

Assistant Vice President at Creative Capital Inc.

Rhys joined Creative Capital in 2015. With a background in analyzing expenses, business models, and investments, he supports CCI’s clients by attending mediation and settlement conferences, assisting with crafting structured settlements, and helping clients obtain better offers by employing CPLR Art. 50-A and 50-B. Rhys has also developed expertise in working on periodic judgments as required by CPLR 5041 under the supervision of Creative Capital’s General Counsel, Marty Jacobson.

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We are a registered provider with 327+ associations and regulatory bodies worldwide. We operate across 29 global markets including Canada, the US, Australia, and the UK. Every course page clearly displays its specific accreditations. Upon completion, you receive a professional certificate that can be validated online. Our certificates include all necessary accreditation details, credit hours, and completion dates, and are formatted specifically to meet the submission requirements of most global regulatory bodies.