Roberta Casper Watson
Roberta Casper Watson
Partner
Practice Areas
Biography
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.
Publications & Media
Publications and News
- 12 Attorneys from The Wagner Law Group to be Recognized in 2025 Edition of The Best Lawyers in America© – EIN Presswire, August 15, 2024 (PDF)
- Benefits Rules Likely to Draw Fresh Fire After High Court Action – Bloomberg Law, July 2, 2024 (PDF)
- Court Split Spells Trouble on Surprise Billing Award Enforcement – Bloomberg Law, June 11, 2024 (PDF)
- Johnson & Johnson Case Signals Employee Drug Price Suits to Come – Bloomberg Law, February 9, 2024 (PDF)
- Workers Poised to Get Benefits as Rule Creates ‘Employees’ – Bloomberg Law, January 29, 2024 (PDF)
- Could Skin Care be the Next Gold Rush Opportunity for Tax-Free FSA Shopping? – Glossy, January 16, 2024 (PDF)
- DOL Proposes to Rescind 2018 Association Health Plan Rule – PLANSPONSOR, December 22, 2023 (PDF)
- DOL Advises Plan Sponsors to Extend Enrollment Period for Employees Losing Medicaid – PLANSPONSOR, July 24, 2023 (PDF)
- FAQ Clarifies Status of In-Network Providers, Facility Fees – PLANSPONSOR, July 10, 2023 (PDF)
- DOL Proposes Limiting Short-Term ‘Junk’ Health Plans – PLANSPONSOR, July 7, 2023 (PDF)
- EBSA Publishes Regulatory Update on Health Facility Fees, Provider Networks – planadviser, July 7, 2023 (PDF)
- First Circuit Illustrates the Importance of the Fiduciary Responsibilities of Health and Welfare Plan Sponsors and Severance Providers Under ERISA – Co-author, Bloomberg Tax Management Compensation Planning Journal, Vol. 50 No. 12, December 2, 2022
- Labor Opinions Are Fair Game for Litigation After Circuit Ruling – Bloomberg Law, August 19, 2022 (PDF)
- Nine Attorneys from Wagner Law Group to be Recognized in 2023 Edition of The Best Lawyers in America© – EIN Newswire, August 18, 2022
- Employer Responses to Overturning of Roe v. Wade – Co-author, LexisNexis Practical Guidance, July 11, 2022
- UBS, Edward Jones And Others Keep Mum About Covering Abortion Travel Costs – Roberta Watson, ADVISORHUB, July 7, 2022 (PDF)
- Employers Providing Abortion Benefits Should Address Compliance Questions – SHRM, June 29, 2022 (PDF)
- Mandated Benefits: 2022 Compliance Guide Mid-Year Update – Co-author, Wolters Kluwer, July 2022
- Companies Urged to Review Abortion Coverage With Roe in Balance – Bloomberg, News, June 8, 2022 (PDF)
- Employers Cautioned as Suits Over COBRA Coverage Notices Add Up – Bloomberg News, April 29, 2022 (PDF)
- Mandated Benefits 2021 Compliance Guide – Co-author, Wolters Kluwer, April 2021
- How Benefits Can Ease Workers’ Return To The Office – Law360, March 31, 2021 (PDF)
- Truncated IRS Guidance Agenda Heartens Benefits Attorneys – Bloomberg Law, November 30, 2020 (PDF)
- Seven Attorneys from The Wagner Law Group Named to 2020 Super Lawyers Lists – November 3, 2020
- Benefits Industry Newsmakers – BenefitsPro, September 7, 2020 (PDF)
- 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
Seminars and Webinars
…
- Practitioner’s Panel – Panelist, 2023 Joint TE/GE Council Employee Plans Annual Meeting, Washington, D.C., February 23 – 24, 2023
- Mental Health Parity Rules and Requirements for Plan Sponsors and Administrators – Panelist, Strafford live CLE webinar, January 4, 2023, 1:00 – 2:30 PM (EST) – Click here for details
- Overturning Roe v. Wade: Impact on Employee Benefit Plans and Next Steps for Plan Sponsors and Administrators – Panelist, Strafford live CLE webinar, September 7, 2022, 1:00 – 2:30 PM (EDT) – Click here for details and registration
- Fiduciary Compliance in ESOP Transactions: Recent DOL Settlement Agreements and Best Practices for Counsel – Strafford live CLE webnar, August 4, 2022, 1:00 – 2:30 M (EDT) – Click here for details and registration
- ERISA Covered Health and Welfare Plan Administration: Compliance, Fiduciary Liability, DOL Enforcement Actions: Impact of the 2021 Consolidated Appropriations Act, Mental Health Parity Rules, Prohibited Transactions, Form 5500 – Co-panelist, Strafford, live CLE webinar, June 23, 2022, 1:00 – 2:30 PM (EDT) – Click here for details
- Employee Benefits Welfare Plan – Speaker, American Bar Association Hybrid 2022 May Tax Meeting, May 12 -14, 2022, Marriott Marquis, Washington, D.C. – More details here
- Employer-Sponsored Health Plan Federal Regulation: ACA, COBRA, ADA, GINA, CAA, MHPAEA, Reporting Requirements – Panelist, Strafford, live CLE webinar, November 23, 2021 1:00 – 2:30 PM (EST) – Click here for details
- Conducting Effective Service Provider RFPs for ERISA Retirement Plans – Panelist, Strafford CLE webinar, July 14, 2021 – Click here for details and registration
- Urgent Health Plan Priorities – COBRA Subsidies, and Health and DCAP FSA Extensions and Expansions – Panelist, The Wagner Law Group Webinar, May 26, 2021, 2:00 – 3:00 PM (EDT) – Recording available here – PowerPoint presentation available here
- ERISA Covered Health and Welfare Plan Administration: Compliance, Fiduciary Liability, DOL Enforcement Actions – Co-panelist, Strafford CLE webinar, April 14, 2021, 1:00 – 2:30 PM (EDT) – Click here for details and registration
- Liability Insurance for ERISA Plan Sponsors: Minimizing Financial Risks During the Pandemic and Economic Downturn – Co-presneter Strafford Webinar, December 2, 2020 – More details here
- Lawyer Insights on SECURE Act Planning and Obligations – Co-panelist with Stephen Wilkes, Financial Experts Network webinar, April 30, 2020, 12:00 – 1:15 PM (ET) – Register here
- 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, 2:00 PM (ET) – Register here
- Employee Benefits Multiple Employers, PEOs and Controlled Groups Update – Panelists, American Bar Association Section of Taxation 2020 Midyear Tax Meeting, January 30 – February 1, 2020, Boca Raton Resort, Boca Raton, FL
- New Individual Coverage and Excepted Benefit HRAs: DOL Guidance and Compliance Challenges for Employers – Panelist, Strafford live CLE webinar, January 29, 2020, 1:00 – 2:30 PM (ET) – Register here
- 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, 1:00 – 2:00 PM (ET) – Recording available here – PowerPoint slides available here
- Fiduciary Compliance in ESOP Transactions: Recent DOL Settlement Agreements and Best Practices for Counsel – Co-panelist, Strafford Live Interactive CLE webinar, June 4, 2019, 1:00 – 2:30 PM (ET)
- 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, 1:00pm-2:30pm (EDT)
- Agencies Issue Final Rule that Expands Duration of Short-Term Limited-Duration Health Insurance – 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, 1:00 – 2:30 PM (ET)
- ERISA Compliance: Implementing Effective Claims Procedures Under Section 503 and DOL Regulations – Webinar for Strafford, June 27, 2018, 1:00 – 2:30 PM (ET)
- Ethical Considerations Regarding Private Opinion Letters for Qualified Plans – Co-panelist, ABA Employee Benefits Spring Update, April 9, 2018, Washington, D.C. – More details here
- ERISA Compliance and Monitoring 401(k) Investments: Safe Harbor Rules and Appointing Advisers – Co-panelist, webinar for Strafford, April 3, 2018 – More details here
- HSAs, FSAs, HRAs and Voluntary Insurance Programs: ERISA vs. Non-ERISA Compliance – Webinar for Strafford, Tuesday, November 28, 2017 – More details here
- 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 – Click here for PowerPoint Presentation (PDF)
- What Every Employer Needs to Know About the Affordable Care Act – PART 2 – Health & Welfare Law Webinar, December 15, 2015
To download the PowerPoint presentation click here - What Every Employer Needs to Know About the Affordable Care Act – PART 1 – Health & Welfare Law Webinar, November 12, 2015
Education
- Harvard University Law School, Cambridge, Massachusetts
- J.D. – 1974
- University of Idaho, Moscow, Idaho
- B.A. – 1971
- Honors: cum laude
- Major: Political Science
- Phi Beta Kappa
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
Professional Associations
- Subcommittee on Special Insurance Problems, Chairman, 1987
- Harvard Club, Vice President of Programs
- Florida West Coast Employee Benefits Council, Member
- Northside Mental Health Center, Board of Directors, 1987
- American Heart Association, Hills City Chapter, Board of Directors, 1988
- 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, Member/Past Chair, 1995 to 1996
- 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, Chair, 1998 to 2001
- 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
- Harvard Club of the West Coast of Florida, Board of Directors
- Florida West Coast Employee Benefits Council, Board of Directors, 1996 to 2003
- Northside Mental Health Center, Board of Directors
- Community Health Purchasing Alliance, District Six (CHPA)
- Tampa Bay Pension Council
Honors
- AV Rated by Martindale Hubbell
- Best Lawyers in America (Employee Benefits Law)
- Florida Super Lawyers, 2006-2007, 2009-2010, 2012-2020
- Florida Council for Community Mental Health, Inc. Board Member of the Year
- The Best Lawyers in America Tampa Bay Lawyer of the Year
- Florida Super Lawyers Corporate Counsel Edition, 2008 and 2010
- 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
Past Positions
- Trenam Kemker, Senior Member, 2011 to 2013
- Trenam Kemker, Shareholder , 1988 to 2011
Law Alerts
Departments Issue Guidance Requiring First Annual “Gag” Attestation by December 31, 2023
By Dannae Delano, Roberta Casper Watson and Barry Salkin The Consolidated Appropriations Act of 2021 (“CAA”) is the most significant compliance challenge for employer health plan sponsors since the Affordable Care Act. Compliance is now required for its provisions...
District Court Once Again Invalidates No Surprises Act Regulations
By Roberta Casper Watson, Dannae Delano and Barry Salkin The No Surprises Act directs the Departments of Treasury, Labor, and Health and Human Services (the “Departments”) to establish a Federal Independent Dispute Resolution Process (the “Federal IDR Process”),...
Congress Enacts Respect for Marriage Act
By, Barry Salkin, Roberta Watson and Jon Schultze n the ordinary course, we would not be advising clients that a statute that a Supreme Court held unconstitutional nine years ago was being removed from the United States Code. However, since the Dobbs decision...
Federal Agencies Issue Group Health Plan Guidance
By Roberta Watson, Barry Salkin and Dannae Delano On December 23, 2022, new guidance applicable to group health plans was issued by federal agencies, as described more fully below. The Center for Medicare and Medicaid Services issued updated fee guidance in...
IRS Announces Expansion of Change in Status Rules for Cafeteria Plans
One of the basic rules under which cafeteria plans operate is that elections are irrevocable except in certain limited circumstances. Further, even when those limited circumstances apply, the change in election must be consistent with the change in status. Legislative...