Disinheriting the IRS: Advanced Trust Strategies, Income Tax Traps, and Audit-Ready

Jonathan G. Blattmachr, Senior Advisor | Pioneer Wealth Partners, LLC

Jonathan G. Blattmachr is a principal at Pioneer Wealth Partners and is widely recognized as a leading authority in estate planning and taxation. Over the course of his career, he has been known for his work in developing and analyzing advanced estate planning strategies and for his substantial contributions to scholarship in trust and tax law. Blattmachr has authored and co-authored numerous articles and publications addressing sophisticated wealth-transfer techniques, and his work has been frequently cited by practitioners and academics in the field. He is also a frequent speaker on estate planning topics and has played a significant role in shaping modern approaches to trust and tax planning.

• Education & Credentials

Jonathan G. Blattmachr is an attorney whose career has focused extensively on estate planning, trusts, and taxation. His professional credentials reflect decades of experience advising on wealth-transfer strategies and the legal frameworks governing estate and trust planning. His background supports a practice centered on complex planning techniques and federal tax considerations affecting individuals and families

• Recognition & Leadership

Blattmachr is widely recognized within the estate planning and tax community for his thought leadership and scholarly contributions. He has received recognition from legal and tax organizations and is frequently cited for his role in advancing the understanding of sophisticated estate planning strategies. His leadership is reflected in his influence on both practitioners and the broader development of planning techniques.

• Professional Involvement

He has been actively involved in legal and tax organizations and has contributed extensively to professional literature in the field of estate planning. Blattmachr has authored or co-authored numerous articles, treatises, and publications addressing advanced trust strategies and wealth-transfer planning, and he regularly participates in professional education initiatives as a speaker and contributor.

• Experience

Throughout his career, Blattmachr has advised individuals, families, and professional advisors on complex estate planning strategies and tax-efficient wealth transfers. His experience includes the development and implementation of advanced planning techniques involving trusts and other structures designed to manage and transfer wealth. He is also known for his role in educating practitioners and contributing to the evolution of estate planning practices through his writing and speaking.

Robert S. Barnett, Partner | Capell Barnett Matalon & Schoenfeld LLP

Robert S. Barnett, JD, Masters (Taxation), CPA, is a founding partner of Capell Barnett Matalon & Schoenfeld LLP, Attorneys at Law. His practice is highly concentrated in the areas of taxation, trusts, estates, corporate and partnership law, and charitable planning. He brings creative and practical solutions to estate and business planning, drawing on extensive experience that includes Surrogate’s Court practice, tax dispute resolution, Tax Court representation, and the structuring of financial transactions and charitable gifts. A prolific lecturer and published author on tax and business law, Mr. Barnett is an active participant on numerous professional and charitable boards.

• Education & Credentials

Mr. Barnett earned his Bachelor of Science degree in accounting from Hofstra University, graduating magna cum laude. He went on to receive his Juris Doctor in 1986 from Fordham University, where he graduated cum laude and served as a member of the Fordham Law Review. He also holds a Master’s degree in Taxation, which he received as the recipient of the highest dean’s award. In addition to his legal credentials, Mr. Barnett holds the designation of Certified Public Accountant (CPA). He is admitted to practice law in New York, Virginia, and Washington, D.C.

• Recognition & Leadership

Mr. Barnett was recognized as a 2024 Top Lawyer of Long Island by the Long Island Herald. He has been selected to the Super Lawyers list from 2021 through 2025. He was named Chair of the New York State Society of CPAs (NYSSCPA) Estate Planning Committee for 2019 and 2020. He currently serves as an adjunct professor in the graduate tax program at Hofstra University and previously held that same role at Long Island University’s School of Professional Accounting.

• Professional Involvement

Mr. Barnett has served on many professional and charitable committees and boards throughout his career. He has lectured extensively before a wide range of organizations, including the American Bar Association, the AICPA, the New York State Society of CPAs, the Nassau County Bar Association, the National Conference of CPA Practitioners, the National Business Institute, St. John’s University, Baruch College, Hofstra University, Long Island University, and numerous others. He has also delivered webinars through platforms including Strafford, Lorman, CPE Link, CPA Academy, and myLawCLE.

• Experience

Mr. Barnett’s practice at Capell Barnett Matalon & Schoenfeld LLP encompasses taxation, trusts and estates, corporate and commercial transactions, tax controversy, and estate administration. His hands-on experience spans Surrogate’s Court proceedings, Tax Court representation, tax dispute resolution, and the structuring of financial transactions and charitable gifts. He has published articles across numerous legal and accounting publications, including the CPA Journal, the New York Law Journal, the Journal of Taxation, the Journal of Accountancy, the Nassau Lawyer, and Investment News, covering topics from passive activity losses and S corporation taxation to estate planning, charitable giving, and cryptocurrency enforcement.

Gregory L. Matalon, Partner | Capell Barnett Matalon & Schoenfeld LLP

Gregory L. Matalon is a founding partner of Capell Barnett Matalon & Schoenfeld LLP whose practice concentrates in estate planning, estate administration, elder law, and Not-for-Profit and Religious Corporations Law. He regularly assists individuals and families in planning for the future through the preparation of Last Wills and Testaments, Trusts, Living Wills and Health Care Proxies, and Durable Powers of Attorney documents, always ensuring that the client’s goals remain primary while building tax-efficient estate plans. He also represents Executors and Trustees in navigating complex federal and state laws governing estates and trusts — work through which he has submitted Private Letter Ruling requests to both the Internal Revenue Service and the New York City Department of Finance, successfully clarifying existing law or, in some cases, establishing new law on behalf of his clients. Mr. Matalon is a frequent lecturer and contributor to legal publications, and he is proud to have represented numerous families who lost loved ones on September 11, 2001, and to have helped establish Lutheran Disaster Response of New York in the aftermath of those tragedies.

• Education & Credentials

Mr. Matalon earned his Bachelor of Arts degree from Skidmore College and his Juris Doctor from Hofstra University School of Law.

• Recognition & Leadership

Mr. Matalon was named a 2024 Top Lawyer of Long Island by the Long Island Herald. He received the Lutheran Schools Association’s 2016 “Spirit of Hope” Award in recognition of his faithful support and model of service to the children, families, and schools of the LSA. He was presented with the “Amigo” award from Transfiguration Lutheran Church in the Bronx for his resolution of a major tax matter on behalf of the congregation. In 2014, the Long Island GLBT Services Network named Capell Barnett Matalon & Schoenfeld LLP a 2014 Equality Award Honoree in connection with his work. As a member of the New York State Bar Association, Mr. Matalon was appointed liaison to the Tax Law Section and was granted a seat on the House of Delegates, the policy-making body of the NYSBA.

• Professional Involvement

Mr. Matalon lectures regularly on estate planning and administration, Medicaid planning, same-sex couples planning, and Religious Corporations Law before a wide range of organizations, including the New York State Bar Association, the Nassau County Bar Association, the Hispanic National Bar Association, LeGaL (LGBT Bar Association of Greater New York), the National Conference of CPA Practitioners, the New York State Society of Certified Public Accountants, and the New York Society of Independent Accountants. He has also lectured at the Interchurch Center, various community-based organizations, and for continuing legal education providers including Lawline, the National Business Institute, and Lorman Educational Services. He is a frequent contributor to the New York Law Journal and has been interviewed by journalists for publications including The Atlantic and Better Homes & Gardens. In the community, he serves as a Board Member of the Queens Community House and as Vice-Chair of the Board of Trustees of the Kew- Forest School, an independent pre-K through 12th-grade college preparatory school in Forest Hills, New York. He previously served as Former Vice-Chair of the Board of Trustees of the Lutheran Schools Association and as Former Vice-Chair of the Small Firm and Solo Practitioners Committee of LeGaL.

• Experience

Mr. Matalon’s practice at Capell Barnett Matalon & Schoenfeld LLP spans estate planning, estate administration, elder law, and Not-for-Profit and Religious Corporations Law. His representation of Executors and Trustees has brought him into areas of unsettled law, where he has successfully sought Private Letter Rulings from the IRS and the New York City Department of Finance to clarify or establish governing authority on behalf of his clients. He has published in the New York Law Journal on topics including taxable gift reporting, estate tax exemptions, and post-ATRA estate planning, and has contributed to the Journal of the Nassau County Bar Association and other outlets. His published insights and media appearances reflect a practice that bridges rigorous legal counsel with accessible public guidance on estate and tax matters.

I. Strategic Irrevocable Trust Design and Drafting Architecture for Durable Outcomes | 1:00pm – 2:00pm

Effective irrevocable trust planning begins with selecting the appropriate strategy and drafting an instrument that can operate reliably over time. This session introduces the core design considerations attorneys must address when structuring advanced trust plans, including aligning planning techniques with client goals, asset profiles, and governance needs. The discussion sets the stage for examining how thoughtful drafting architecture and structural flexibility can support durable, long-term planning outcomes.

This session focuses on the planning and drafting decisions that determine whether an irrevocable trust structure will function as intended over time. It explores client strategy intake, technique selection among structures such as SLATs, GRATs, and sales to trusts, and how attorneys align these tools with asset types, liquidity needs, and control objectives. The discussion also addresses drafting architecture, including distribution standards, trustee and protector roles, governance safeguards, and structural flexibility mechanisms designed to preserve long-term operability.

Break | 2:00pm – 2:10pm

II. Trust Administration, Tax Risk Management, and Defense Readiness for Irrevocable Planning | 2:10pm – 3:10pm

Once a trust is funded, its success depends on disciplined administration, coordinated professional oversight, and careful attention to tax compliance. This session introduces the operational and risk-management challenges attorneys and fiduciaries face when managing irrevocable trusts in practice. It prepares participants to examine the processes, controls, and documentation strategies necessary to maintain tax efficiency and defend the structure if disputes or regulatory scrutiny arise.

This session examines how irrevocable trusts should be operated after funding to avoid income-tax mistakes, state tax exposure, and fiduciary disputes. Attendees will review the first-year administration framework, including documentation practices, operational controls, and coordination among trustees, attorneys, and tax professionals. The session also addresses audit preparedness, defensible recordkeeping, and practical repair strategies such as trust modification, decanting, or settlement tools when operational issues arise