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Watson, Roberta Casper

Roberta Casper Watson - Tampa, FL

Attorney at The Wagner Law Group

Lawyers in Tampa, FL

100 North Ashley Drive Suite 600 Tampa, FL 33602

Updated: 03/16/2026

Attorney Information

Overview

Roberta Casper Watson is the leader of the firm's health and welfare group. Her practice is in the areas of ERISA and employee benefits, with a focus on pension and profit sharing plans as well as health and welfare benefits, including COBRA, HIPAA, and the Affordable Care Act. Roberta also concentrates in ERISA fiduciary decision making and employee stock ownership plans.

Within the employee benefits field, Roberta's extensive experience goes beyond ERISA and impacts other areas of law. For example, she is skilled in determining how employee benefits affect family law and labor law, including the American Disabilities Act, the Age Discrimination in Employment Act, and the Family and Medical Leave Act. As a result, she applies specific provisions that must be integrated into benefit plans - so as to comply with these rules and satisfy government reporting requirements while fully informing participants. Additionally, she spearheads litigation when fiduciary breaches occur in employee benefit plans.

Roberta is an active member and a past chair of the American Bar Association Tax Section's Employee Benefits Committee, the ABA's Joint Committee on Employee Benefits (JCEB), the ABA Health Law Section's Employee Benefits Interest Group, the Harvard Club, and Florida West Coast Employee Benefits Council. She is a member of the Tampa Bay Pension Council and is a charter member of the American College of Employee Benefits Counsel.

Prior to joining The Wagner Law Group, Roberta was a shareholder and senior member at a leading Tampa law firm.


Awards and Honors

Honors

  • The Best Lawyers in America Tampa Bay Lawyer of the Year - Employee Benefits (ERISA) 2026
  • Chambers USA - 2025
  • AV Rated by Martindale Hubbell
  • Best Lawyers in America (Employee Benefits Law), 1995 - 2026
  • Florida Super Lawyers, 2006-2007, 2009-2010, 2012-2020
  • Florida Council for Community Mental Health, Inc. Board Member of the Year, 1994 - Present
  • The Best Lawyers in America Tampa Bay Lawyer of the Year - Employee Benefits (ERISA), 2012 - Present
  • Florida Super Lawyers Corporate Counsel Edition, 2008 and 2010, 2008 - Present
  • Best Lawyers, 1995-Present
  • American College of Employee Benefits Counsel - Charter Fellow
  • Marquis Who’s Who Lifetime Achievement Award – 2018 Edition of Who’s Who in America
  • 2012 Lawyer of the Year - Employee Benefits (ERISA) Law Best Lawyers
  • 2019 Lawyer of the Year - Employee Benefits (ERISA) Law Best Lawyers
  • The Best Lawyers in America (Employee Benefits/ERISA Law) – 1995-2016
  • The Best Lawyers in America – Tampa Bay Lawyer of the Year (Employee Benefits Law) -2012

Education

  • Legal Education

    • Harvard Law School, Cambridge, Massachusetts, 1974
      J.D.
  • Non Legal Education

    • University of Idaho, Moscow, Idaho, 1971
      B.A.
      Honors: cum laude
      Major: Political Science

Past Positions

  • Trenam Kemker, Senior Member, 2011 - 2013
  • Trenam Kemker, Shareholder, 1988 - 2011

Classes and Seminars

  • Conducting Effective Service Provider RFPs for ERISA Retirement Plans - Panelist, Strafford CLE webinar, July 14, 2021
  • Urgent Health Plan Priorities - COBRA Subsidies, and Health and DCAP FSA Extensions and Expansions , Panelist, The Wagner Law Group Webinar, May 26, 2021
  • ERISA Covered Health and Welfare Plan Administration: Compliance, Fiduciary Liability, DOL Enforcement Actions, Co-panelist, Strafford CLE webinar, April 14, 2021
  • iability Insurance for ERISA Plan Sponsors: Minimizing Financial Risks During the Pandemic and Economic Downturn, Co-presneter Strafford Webinar, December 2, 2020
  • New Legislation Affecting Workplace Health & Welfare Benefits, Co-panelist with Dannae Delano and Barry Salkin, The Wagner Law Group free webinar, May 15, 2020
  • Lawyer Insights on SECURE Act Planning and Obligations, Co-panelist with Stephen Wilkes, Financial Experts Network webinar, April 30, 2020
  • Merger, Divestiture and Acquisitions and Employee Benefits - Co-panelist with David Gabor, Izzy Goldowitz and Mark Poerio, free live webinar with Institutional Investment Consulting Inc., March 24, 2020
  • New Individual Coverage and Excepted Benefit HRAs: DOL Guidance and Compliance Challenges for Employers - Panelist, Strafford live CLE webinar, January 29, 2020
  • Being Smart About M&A-Related Benefit Plan and Employment Issues - Co-panelist with David Gabor, Mark Poerio and Roberta Watson, The Wagner Law Group FREE webinar, June 11, 2019
  • Fiduciary Compliance in ESOP Transactions: Recent DOL Settlement Agreements and Best Practices for Counsel , Co-panelist, Strafford Live Interactive CLE webinar, June 4, 2019
  • Florida West Coast Employee Benefits Council's Annual Educational Workshop, Roberta Watson (Council President), opening remarks, April 22, 2019, Centre Club, Tampa, FL
  • Structuring Options for ESOP Transactions: Advanced Techniques for ERISA Counsel and Plan Sponsors , Webinar for Strafford, Tuesday, September 25, 2018
  • Agencies Issue Final Rule that Expands Duration of Short-Term Limited-Duration Health Insurance , Dan S. Brandenburg and Roberta Casper Watson, American Bar Association, Employee Benefits Committee Newsletter, August 2018
  • ERISA Reporting and Disclosure: Statutory Exclusions and Exemptions , Co-panelist, Strafford CLE webinar, August 14, 2018
  • ERISA Compliance: Implementing Effective Claims Procedures Under Section 503 and DOL Regulations
  • Ethical Considerations Regarding Private Opinion Letters for Qualified Plans - Co-panelist, ABA Employee Benefits Spring Update, April 9, 2018, Washington, D.C.
  • ERISA Compliance and Monitoring 401(k) Investments: Safe Harbor Rules and Appointing Advisers – Co-panelist, webinar for Strafford, April 3, 2018
  • HSAs, FSAs, HRAs and Voluntary Insurance Programs: ERISA vs. Non-ERISA Compliance - Webinar for Strafford, Tuesday, November 28, 2017
  • Protecting Yourself: Private Determination Letters, Insurance, and Indemnification – Co-presenter with Jon Schultze at NCEO’s Fall ESOP Festival, October 3, 2017, at the Grand Hyatt, Tampa Bay, FL
  • Conducting Effective Service Provider RFPs for ERISA Retirement Plans - Webinar for Stafford Live CLE Webinars, July 13, 2017
  • What Every Employer Needs to Know About the Affordable Care Act - PART 2 - Health & Welfare Law Webinar, December 15, 2015
  • What Every Employer Needs to Know About the Affordable Care Act - PART 1 - Health & Welfare Law Webinar, November 12, 2015

Published Works

Articles

  • Mandated Benefits 2021 Compliance Guide - Co-author, Wolters Kluwer, April 2021
  • How Benefits Can Ease Workers' Return To The Office - Law360, March 31, 2021
  • Truncated IRS Guidance Agenda Heartens Benefits Attorneys - Bloomberg Law, November 30, 2020
  • Seven Attorneys from The Wagner Law Group Named to 2020 Super Lawyers Lists - November 3, 2020
  • Benefits Industry Newsmakers - BenefitsPro, September 7, 2020
  • Employee Retention Tax Credit Under the CARES Act - Co-author with Barry Slakin and Livvia Quan Aber, The Wagner Law Group Law Alert, May 21, 2020
  • Welfare Plan Issues During the Covid-19 Emergency - Co-author with Barry Salkin, Bloomberg Law, April 2020
  • The Families First Coronavirus Response Act Updated to Include Coronavirus Aid, Relief, and Economic Security Act Provisions - Co-author with Barry Salkin and Virginia Peabody, The Wagner Law Group Law Alert, April 1, 2020
  • The Families First Coronavirus Response Act - Co-author with Barry Salkin and Virginia Peabody, The Wagner Law Group Law Alert, March 26, 2020
  • Agencies Issue Proposed Rules Regarding Health Care Transparency - Co-author with Barry Salkin, The Wagner Law Group Law Alert, March 19, 2020
  • 4 Tips For Complying With Coronavirus Benefit Mandates - Law360, May 1, 2020
  • Sharing of Workers’ 401(k) Data ‘New Frontier’ in Litigation - Roberta Casper Watson, Bloomberg Law, February 14, 2020
  • Mandated Benefits 2020 Compliance Guide - Co-authors Katherine Brustowicz, Dannae Delano, David Gabor, Barry Salkin and Marcia Wagner, Wolters Kluwer, December 2019
  • An Employer's Guide to Navigating the ACA Reporting Requirements - Roberta Watson and Dannae Delano, The Practical Lawyer, December 2018 Reprinted with permission from ALI CLE
  • An Employer's Guide to Navigating the ACA Reporting Requirements - Roberta Watson and Dannae Delano, The Practical Tax Lawyer, Fall 2018 Reprinted with permission from ALI CLE
  • Health Care Reform Proposal - Wolters Kluwer Journal of Pension Benefits, Spring 2018, vol. 25, no. 3
  • Realtors Nearly Sold on Association Health Plan Rule - BNA, February 28, 2018
  • Fate of health reform’s 30-hour rule uncertain - Employee Benefit Adviser, July 14, 2017
  • 5 ways to ensure an HSA isn't subject to ERISA - Investment News, July 7, 2017
  • Should ERISA exemption be sought for voluntary? - Employee Benefit Adviser, November 14 2016
  • Broker input anticipated on new OT rules - Employee Benefit Adviser, November 08 2016
  • Can UAW pull off brave, new health deal? - Detroit Free Press, August 23, 2015
  • Health-care 'Cadillac' tax could be hurdle in auto talks - Detroit Free Press, August 19, 2015
  • Health care tax could be hurdle in UAW talks - Detroit Free Press, August 18, 2015
  • Experts Weigh in on the 'Cadillac Tax' - AccountingWeb, July 1, 2015
  • Beyond 401(k): Program Will Take a Peek at New Pension Model - In Business Madison (ibmadison.com), October 31, 2014

Bar Admissions

  • Massachusetts, 1974
  • Florida, 1985
  • U.S. Supreme Court, 1979
  • U.S. Tax Court, 1979
  • U.S. District Court Middle District of Florida
  • U.S. District Court Southern District of Florida
  • U.S. District Court District of Massachusetts
  • U.S. Court of Appeals 1st Circuit
  • Supreme Court of Florida
  • Supreme Judicial Court of Massachusetts

Other Affiliations

  • Subcommittee on Special Insurance Problems, 1987 - Present (Chairman)
  • Harvard Club (Vice President of Programs)
  • Florida West Coast Employee Benefits Council (Member)
  • Northside Mental Health Center, 1987 - Present (Board of Directors)
  • American Heart Association, Hills City Chapter, 1988 - Present (Board of Directors)
  • Unitarian Universalist Foundation (Trustee)
  • Employee Benefits Interest Group of the American Bar Association's Health Law Section (Past Chair)
  • ABA Tax Section's Employee Benefits Committee, 1995 - 1996 (Member/Past Chair)
  • ABA's Joint Committee on Employee Benefits ("JCEB") (Past Chair)
  • American College of Employee Benefits Counsel (Charter Fellow)
  • American Law Institute (Member)
  • Tampa Bay Pension Council (Member)
  • American Bar Association, Health Law Section, Employee Benefits Interest Group, 1998 - 2001 (Chair)
  • The Florida Bar, Real Property, Probate and Trust Law Section (Employee Benefits Committee, Chair)
  • Hillsborough County Bar Association
  • The ESOP Association
  • Gulf Coast TE/GE Council (President)
  • American Bar Association, Labor and Employment Section, Employee Benefits Committee
  • American Law Institute
  • Member of CHIPRA Task Force, 2010 - Present
  • Harvard Club of the West Coast of Florida (Board of Directors)
  • Florida West Coast Employee Benefits Council, 1996 - 2003 (Board of Directors)
  • Northside Mental Health Center (Board of Directors)
  • Community Health Purchasing Alliance, District Six (CHPA)
  • Tampa Bay Pension Council

Fraternities and Sororities

  • Phi Beta Kappa

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