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 is a tax attorney with Caplin & Drysdale, Chartered, where he focuses his practice on complex federal tax matters involving estate planning, trusts, and high-net-worth individuals. His work centers on advising clients in connection with sophisticated wealth-transfer strategies and navigating the tax implications of estate, gift, and income tax planning. Barnett regularly counsels individuals, families, and fiduciaries on structuring transactions and trust arrangements designed to align with both legal requirements and long-term planning objectives. His practice reflects a concentration on technically complex tax issues, particularly those arising in the context of trusts and estates.

• Education & Credentials

Robert S. Barnett is a licensed attorney whose credentials reflect a focus on federal taxation, estate planning, and wealth-transfer strategy. His legal training and professional qualifications support his work advising clients on estate, gift, and income tax matters, including the structuring and implementation of irrevocable trust arrangements. His credentials are consistent with a practice devoted to complex tax planning and compliance.

• Recognition & Leadership

Barnett has developed recognition within the tax law community for his work in sophisticated estate planning and federal tax matters. His professional standing reflects his experience in addressing complex planning issues and advising on transactions that require careful navigation of federal tax rules. His role within his firm also reflects leadership in handling matters involving trusts, estates, and wealth-transfer planning.

• Professional Involvement

He has been involved in professional organizations and legal communities focused on tax law and estate planning. Through this involvement, Barnett contributes to ongoing discussions regarding developments in federal taxation, planning strategies, and the evolving regulatory environment affecting trusts and estates.

• Experience

Barnett’s experience includes advising high-net-worth individuals, families, and fiduciaries on estate and gift tax planning, trust structuring, and related federal tax issues. His practice encompasses the design and implementation of planning strategies involving irrevocable trusts and wealth-transfer techniques, as well as guidance on tax-efficient structuring of assets and transactions. He regularly works on matters requiring detailed analysis of tax rules and their application to complex estate planning scenarios.

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

Gregory L. Matalon is a partner at Capell Barnett Matalon & Schoenfeld LLP, where he concentrates his practice in estate planning, estate and trust administration, elder law, and Not-for-Profit and Religious Corporations Law. He advises individuals and families on the preparation of wills, trusts, and advance directives, and represents fiduciaries in the administration of estates and trusts. His practice includes addressing federal and state tax issues affecting estates and trusts, and he has experience obtaining Private Letter Rulings from the Internal Revenue Service and rulings from the New York City Department of Finance. Matalon is also an active lecturer on estate planning, estate administration, and elder law topics, and has presented for bar associations, accounting organizations, and continuing education providers. He has contributed to publications and has been interviewed on matters relating to estate planning.

• Education & Credentials

Gregory L. Matalon received his J.D. from Hofstra University School of Law and his B.A. from Skidmore College. He is admitted to practice law in New York.

• Recognition & Leadership

Matalon has been recognized by Super Lawyers in the area of estate planning and probate. He has also received community-based recognition, including the Lutheran Schools Association “Spirit of Hope” Award. He has held leadership roles within the New York State Bar Association, including service in its House of Delegates and as a liaison to the Tax Law Section.

• Professional Involvement

Matalon is actively involved in professional and community organizations. He has lectured for the New York State Bar Association, the Nassau County Bar Association, the New York State Society of Certified Public Accountants, Lawline, and the National Business Institute. He has also served in leadership and board roles with organizations including Queens Community House and The Kew-Forest School, and has been involved with the LGBT Bar Association of Greater New York and the Lutheran Schools Association.

• Experience

Matalon advises clients on estate planning strategies and the preparation of wills and trusts, and represents executors and trustees in estate and trust administration. His work includes addressing complex legal and tax issues arising in fiduciary matters and assisting not-for-profit and religious organizations with governance and compliance matters. He has also been involved in community efforts, including assisting families affected by the events of September 11, 2001 and helping establish Lutheran Disaster Response of New York.

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.