The Great Wealth Transfer and the Coming Wave of Probate Litigation: Contested Estates, Fiduciary Claims, and Heirs’ Property Disputes Through 2040

Brittany Kaczmarczyk, Associate | Reminger Co

Brittany Kaczmarczyk is an associate in Reminger Co., LPA’s Cleveland and Akron offices, where she focuses her practice on estates, trusts, probate litigation, and guardianship. She represents clients in the pursuit and defense of trust and will contests, power of attorney abuse, declaratory judgments to invalidate financial or real estate transactions, fiduciary liability, and breach of trust. Brittany counsels clients through all phases of the probate litigation process, including factual investigation, pleadings, discovery, motion practice, mediation, evidentiary hearings, and trial. Beyond litigation, she handles estate and trust administration and assists clients in applying for, as well as personally serving as, guardian. She has reviewed hundreds of thousands of pages of documents, researched complex issues of law, developed case strategies, and obtained results for her clients through motion practice, mediation, and trial.

• Education & Credentials

Brittany earned her J.D., magna cum laude, from CSU College of Law in 2022, where she served as Executive Editor of the Cleveland State Law Review. She holds an M.A. in Biology (2019) from Kent State University, as well as a B.S. in Biology (2017) and a B.A. in Paralegal Studies (2017), both from Kent State University. She is admitted to practice in the State of Ohio (2022) and before the U.S. District Court, Northern District of Ohio (2024).

• Recognition & Leadership

Brittany has been recognized by The Best Lawyers in America: Ones to Watch for Litigation – Trusts and Estates. She received the CALI High A Award for Health Care Law and Ethics. She is a 2023 graduate of FDCC Ladder Down Cleveland and serves as an Executive Committee Member. During law school, she served as president of Cleveland State’s law school chapter of Phi Alpha Delta law fraternity.

• Professional Involvement

Brittany is involved with FDCC Ladder Down Cleveland, the William K. Thomas Inn of Court, the Ohio State Bar Association, the Cleveland Metropolitan Bar Association, and the Akron Bar Association. She regularly presents on issues involving probate litigation, with speaking engagements including “Challenging a Will or Trust: Complex Tactics for Experienced Practitioners,” “Proving or Defending Undue Influence in Litigation: Evidence, Experts, Remedies,” the Reminger Co., LPA Advanced Probate Law Institute, and “Understanding Psychiatric Advanced Directives and Supported Decision Making.” She has published in the Probate Law Journal of Ohio. She also remains active in the community through her continued involvement in Ladder Down, Cleveland, and several bar associations.

• Experience

Brittany practices in estates and trusts, estates, trusts, and probate litigation, estate and trust administration, and guardianships. Her litigation experience spans trust and will contests, power of attorney abuse, declaratory judgments to invalidate financial or real estate transactions, fiduciary liability, and breach of trust, guiding clients through every phase from factual investigation through trial. Her results include a unanimous jury verdict in Summit County Probate Court in November 2024 awarding $110,000 plus attorney fees on behalf of four trust beneficiaries in a breach of fiduciary duty action, and a March 2024 Motion for Judgment on the Pleadings in Cuyahoga County Probate Court in a will contest case, including dismissal of an Intentional Interference with an Expected Inheritance claim.

Michael Brody, Associate | Reminger Co

Michael Brody is an associate in Reminger’s Cleveland office, where he focuses his practice primarily on litigating private and family wealth disputes arising from wills, trusts, power of attorney and fiduciary misconduct, and non-probate transfers of assets. He also assists clients with estate and trust planning and administration and provides guardianship services. Recognizing that estate and trust disputes often involve heightened emotions and unique family dynamics alongside their inherent economic considerations, Michael works closely to understand these factors so he can counsel clients effectively and help them reach pragmatic, equitable solutions.

• Education & Credentials

Michael earned his J.D., magna cum laude, from Cleveland State University College of Law in 2023, where he made the Dean’s List, served on the CSU Law Moot Court Team, contributed as a writer for “The Gavel,” the school’s student newspaper, and received CALI “High A” Awards in Appellate Practice Clinic and Advanced Brief Writing. He holds a B.A. in Political Science, magna cum laude, from John Carroll University, conferred in 2020, where he was named to the Dean’s List. He is admitted to practice in the State of Ohio and before the U.S. District Court for the Northern District of Ohio, both in 2023.

• Recognition & Leadership

Michael has been recognized by The Best Lawyers in America: Ones to Watch for Litigation – Trusts and Estates. He received the Best Brief Award at the Chicago Bar Association Moot Court Competition in November 2022 and, during his undergraduate studies, earned the Kathleen L. Barber Scholastic Achievement Award from the Department of Political Science in 2020

• Professional Involvement

Michael is a member of the Ohio State Bar Association, the Cleveland Metropolitan Bar Association, and the American Bar Association. His speaking engagements include “Screening Probate Cases Before You File,” “Proving or Defending Undue Influence in Litigation: Evidence, Experts, Remedies,” “Fiduciary Misconduct Disputes in Detail,” the Butler County Probate Seminar, and the Reminger Co., LPA Advanced Probate Law Institute presented before the Columbus Bar Association.

• Experience

Michael concentrates his practice on estates, trusts, and probate litigation, estate and trust administration, estate planning, and guardianships. He represents clients in private and family wealth disputes involving wills, trusts, powers of attorney, fiduciary misconduct, and non-probate transfers of assets. In a representative matter before the Cuyahoga County Probate Court, Michael and Paul Shugar secured a favorable result in a trust dispute: after the trustee failed to communicate, manage the trust, or vacate the trust property, they brought the breach-of-trust case to an evidentiary hearing, where Michael established damages and the Court removed the trustee, appointed an independent fiduciary, and awarded the client a $15,900 estate debt, $24,000 in unpaid rent, full reimbursement of trust expenses, and attorney’s fees. He joined Reminger’s Cleveland office in December 2023.

Stephen Crofford, Vice President | Cumberland Trust

Stephen Crofford, Jr. serves as Vice President and Senior Fiduciary Counsel of Cumberland Trust, which he joined in 2016. In this role he reviews trust agreements and last wills and testaments from states across the country and drafts documents relating to the administration of trusts and estates. He provides counsel to Cumberland Trust on administrative questions that may arise and offers independent legal analysis of trusts, estates, and litigation matters. Stephen also has experience reviewing and preparing client documents and working with unique, illiquid, and hard-to-value assets held in trust.

• Education & Credentials

Stephen received a B.S. in Political Science from the University of Tennessee at Chattanooga and a J.D. from Belmont University College of Law in Nashville. He is licensed to practice law in Tennessee.

• Recognition & Leadership

Stephen has been accepted into Class III of the Southeast Fellows Institute of the American College of Trust and Estate Counsel (ACTEC), beginning in Fall 2025 and concluding in Spring 2026.

• Professional Involvement

Stephen serves on the Tennessee Bankers Association Trust Legislative Committee and is a member of the Tennessee Bar Association, the Nashville Estate Planning Council, and the Estate Planning Council of Middle Tennessee. He is a frequent nationwide speaker on topics related to trust and estate matters and legislation, and he has been published in the ACTEC Law Journal and in Trusts & Estates.

• Experience

Stephen serves as Vice President and Senior Fiduciary Counsel of Cumberland Trust, where he reviews and drafts documents relating to trust and estate accounts, reviews trust agreements and last wills and testaments from states across the country, and prepares documents relating to the administration of trusts and estates. He provides counsel on administrative questions and independent legal analysis of trusts, estates, and litigation matters, and he has experience reviewing and preparing client documents and working with unique, illiquid, and hard-to-value assets held in trust.

Thomas E. Simmons | South Dakota Knudson School of Law

Thomas E. (Tom) Simmons is a tenured professor at the University of South Dakota Knudson School of Law, where he holds the McDowell, King, & South Dakota Trust Company Chair in Trust and Estate Law. His teaching and scholarship concentrate on trusts, estates, probate, attorney ethics, fiduciaries, and the estate tax, and his courses include Trusts & Wills, Estate Planning, Professional Responsibility, Remedies, a pair of Tribal Wills Clinic practicum courses, and occasionally a seminar titled Holocaust Law. He serves as a Commissioner of the Uniform Law Commission and an Associate Justice on the Rosebud Sioux Tribe Supreme Court. He is also the author of three collections of poetry: Tod Browning Looseleaf Encyclopedia, S is for Sentence, and Soviets on Venus.

• Education & Credentials

Tom Simmons earned his J.D. from the University of South Dakota School of Law in 1998, a B.S. in Education and English from the University of South Dakota in 1991, and a Graduate Certificate in Christian Wisdom from Holy Apostles College and Seminary in 2021. He is admitted before the South Dakota Bar, the United States Supreme Court, the U.S. Court of Appeals for the 8th Circuit, the U.S. District Court for the District of South Dakota, and the United States Tax Court. He is also admitted to practice before the Rosebud Sioux, Flandreau Santee Sioux, and Yankton Sioux Tribal Courts, and is an Accredited Attorney with the U.S. Department of Veterans Affairs, Office of General Counsel.

• Recognition & Leadership

Tom Simmons is the recipient of the Cutler Award for Excellence in Legal Education (2016) and has twice received the John Wesley Jackson Memorial Award for Outstanding Professor of Law (2018 and 2020). His additional honors include the AALS Pro Bono Honor Roll (2024), an AV Preeminent rating from Martindale-Hubbell, recognition among America’s Most Honored Lawyers, and selection as Best Lawyers’ Lawyer of the Year for Trusts and Estates in Sioux Falls (2020). In leadership and fiduciary capacities, he serves as an Associate Justice on the Rosebud Sioux Tribe Supreme Court and a Commissioner of the Uniform Law Commission, and he holds the McDowell, King, & South Dakota Trust Company Chair. He is an academic fellow and former state chair of the American College of Trust and Estate Counsel, a fellow of the American College of Tax Counsel, and a life fellow and state chair of the American Bar Foundation.

• Professional Involvement

Tom Simmons is an Academic Fellow and former state chair of the American College of Trust and Estate Counsel (ACTEC), a Fellow of the American College of Tax Counsel, and a Life Fellow and state chair of the American Bar Foundation. He serves as a Commissioner of the Uniform Law Commission and on the South Dakota State Bar’s Ethics Committee. A frequent continuing-legal-education presenter on trusts, estates, fiduciary, tax, and ethics topics, his scholarship has appeared in leading journals including the Elder Law Journal, the Missouri Law Review, the Gonzaga Law Review, and the South Dakota Law Review.

• Experience

Tom Simmons has taught at every educational level, from pre-K (in a Head Start program) and primary school (in Rapid City), to secondary school (in Japan), to undergraduates (in a paralegal studies program), and finally to law students. At the Knudson School of Law his courses include Estate Planning, Professional Responsibility, Trusts & Wills, the Tribal Wills practicum, and Remedies. Prior to joining the academy, he was a partner with the law firm of Gunderson, Palmer, Nelson & Ashmore; today he serves in an of counsel role with the Thompson Law firm. His practice and consulting work center on trusts, probate, ethics, and the estate tax, and he regularly serves as a consultant and expert in litigation involving the federal estate tax, legal malpractice, and fiduciary administration.

David Fowler Johnson, Fiduciary Litigator | Winstead PC

David Fowler Johnson is widely recognized as one of the go-to fiduciary litigators in Texas. His practice focuses on trust, estate, and closely held business disputes. A frequent writer and speaker, David is known around the state as a thought leader in the fiduciary area. His award-winning blog, The Fiduciary Litigator, features recent case law, legislative changes, and other precedent that impacts fiduciaries in Texas. Based in Winstead PC’s Fort Worth office, his work spans both contested litigation and a transactional practice serving trust departments.

• Education & Credentials

David earned his J.D. from Baylor Law School in 1997, graduating magna cum laude. While there, he received the Mid-Year Law Award and the Baylor Law Review, was named to the Academic Dean’s List, and was the recipient of multiple scholarships. He earned his B.B.A. in Accounting from Baylor University in 1994. He was admitted to the Texas bar in 1997. David is one of twenty attorneys in Texas, of the 84,000 licensed, who holds triple Board Certification in Civil Trial Law, Civil Appellate, and Personal Injury Trial Law by the Texas Board of Legal Specialization. He is licensed and has practiced in the U.S. Supreme Court; the Fifth, Seventh, and Eleventh Federal Circuits; the Federal District Courts for the Northern, Eastern, and Western Districts of Texas; the Texas Supreme Court; and various Texas intermediate appellate courts.

• Recognition & Leadership

David received the JD Supra 2020 Readers’ Choice Award for Wealth Management, marking his third consecutive year earning such an award. He was also named a “Go-To Thought Leader” in Fiduciary Litigation by the National Law Review in 2020. He currently serves on the board of the Texas Board of Legal Specialization, the Texas State Bar’s group that certifies attorneys in specialties, and he was previously on the commission that wrote and graded the civil trial law examination.

• Professional Involvement

David has given over 300 legal education presentations to bar groups, industry groups, and clients in the fiduciary and general litigation areas, and has served as an adjunct professor at Baylor University Law School and Texas Wesleyan Law School. He has published twenty law review articles, which have been cited as authority repeatedly by the Texas Supreme Court and Texas courts of appeals, as well as by other jurisdictions including the Supreme Court of Iowa and a federal district court in Pennsylvania. His articles have also been cited by leading commentators such as McDonald & Carlson and William V. Dorsaneo, and across numerous law journals nationwide.

• Experience

David’s trust and estate practice covers will contests, elder abuse, mental competency, undue influence, trust modification, breach of fiduciary duty, and related claims, along with trust decanting, severance and joinder, account and power of attorney disputes, judicial instruction suits, heirship proceedings, fiduciary removal, and accountings. He also maintains a transactional practice for trust departments and has been retained as an expert on fiduciary duties, fiduciary compensation, and elder abuse. His trial experience includes representing banks and individual fiduciaries in significant trust disputes, including a federal class action involving more than 220 trusts. In closely held business disputes, or business divorce, David enforces minority ownership rights, handles shareholder-derivative litigation, and advises majority owners, with trial experience that includes a business divorce involving over $100 million in assets. His practice areas at the firm include Appellate, Business Divorce, Business Litigation, Infrastructure & Eminent Domain, and Fiduciary Litigation.

SESSION 1 – Why Probate Caseloads Are About to Explode | 1:00pm – 1:30pm

This session maps the demographic and economic forces driving the projected probate litigation surge through 2040: boomer wealth concentration, Census aging projections, cognitive decline, and the estate planning gap, giving attorneys a quantitative framework for the caseload ahead.

SESSION 2 – Litigating Fiduciary Breach Claims | 1:30pm – 2:00pm

This session examines UTC §§ 801–813 duty architecture, self-dealing under the no-further-inquiry rule, surcharge and removal remedies, POA agent breach, financial elder abuse statutes, and tortious interference with inheritance expectancy across multiple jurisdictions.

BREAK | 2:00pm – 2:10pm

SESSION 3 – Litigating Capacity and Undue Influence Cases | 2:10pm – 2:40pm

This session covers the Cunningham capacity test, insane delusion doctrine, and Restatement § 8.3 burden-shifting, plus lucid interval evidence, forensic neuropsychological expert testimony, and the strategic choice between capacity and undue influence theories.

SESSION 4 – Resolving Inherited Real Property Disputes | 2:40pm – 3:10pm

This session addresses the Uniform Partition of Heirs Property Act’s procedural protections, IRC § 1014 step-up basis allocation among co-heirs, and reverse mortgage payoff timelines under HUD Mortgagee Letter 2023-23’s Cash-for-Keys provisions.