Samantha E. Weissbluth
Partner | Chicago, IL
Sam is one of Chicago’s premier estate and trust litigation attorneys with over 20 years of problem-solving experience.
Jonathan Strouse concentrates on representing clients involved in litigation, federal tax litigation, and federal tax controversies, including audits and appeals.
Jonathan has represented numerous taxpayers across diverse boundaries, including trusts, estates, federally recognized Indian tribes and tribal members, municipal governments, foreign taxpayers, hedge funds, high-net-worth individuals, qualified ERISA plans (including leveraged and non-leveraged ESOPs), accountants, tax-exempt entities, TEFRA partnerships, individuals involved in Derivium transactions, and S and C corporations (publicly traded and privately held corporations).
Jonathan has extensive experience litigating cases on behalf of taxpayers in the U.S. Tax Court, as well as the U.S. District Court. A list of his more recent cases can be viewed by clicking here.
He has also represented hundreds of taxpayers before the Internal Revenue Service on a wide variety of collection, examination, and appeal matters, including listed transactions and other tax avoidance matters, foreign tax issues, “wealth squad” examinations, “Midco” and section 6901 transactions, valuation issues, domestic and foreign offshore voluntary disclosures including streamlined filings, FBAR issues, the trading safe harbor pursuant to Section 864(b), information reporting issues, penalty matters pursuant to Sections 6662 and 6707A, mediation proceedings pursuant to Rev. Proc. 2009-44, transfer tax issues, and various other trust, estate, corporate, partnership, individual, employment, and excise tax matters.
Before entering law school, Jonathan practiced as a certified public accountant in public accounting for five years. He regularly counsels other attorneys, certified public accountants, and enrolled agents throughout the United States and foreign countries regarding their representation of taxpayers before the Internal Revenue Service.
Capabilities
Estate & Trust Administration
Estate & Trust Litigation
Speeches & Publications
Co-Presenter, “Primer on Discovery Issues for Estate Planners,” IICLE Estate Planning Short Course (May 2025)
Co-Author, “Will Contests,” IICLE Litigating Disputed Estates, Trusts, Guardianships and Charitable Bequests (2023)
Co-Author, “Contested Claims,” IICLE Litigating Disputed Estates, Trusts, Guardianships and Charitable Bequests (2023)
Co-Author, “Admitting Wills to Probate,” IICLE Litigating Disputed Estates, Trusts, Guardianships and Charitable Bequests (2023)
“Will & Trust Contests”, published in the handbook entitled Causes of Action (Illinois Institute for Continuing Legal Education, 2011)
“Heirship, Adoption & Paternity”, IICLE Webinar (2010)
Click here for full list.
Representative Matters
Sam successfully prevailed in a bench trial in defending a client against her ex-husband’s effort to enforce a 15-year-old promissory note.
In representing a charity against a decedent’s off-shore asset protection trust, Sam was an essential member of the litigation team, achieving a victory in the Illinois Supreme Court.
Sam successfully settled a tortious interference with inheritance claim brought by three sisters against a fourth sister – alleging mistreatment and undue influence exerted upon their elderly and infirm mother. The turning point occurred when the defendant admitted to accelerating her mother’s death, resulting in an amended complaint pursuant to Illinois’ “Slayer Statute.”
In a hotly contested case involving heirship, paternity, and DNA testing, Sam successfully defended an action on behalf of a decedent’s brother.
In a highly publicized case brought by the Illinois Attorney General against an investment company seeking treble and punitive damages for an alleged violation of the Charitable Trust Act, Sam briefed an ultimately successful motion that led to the dismissal of her client as a party defendant because it did not qualify as a charitable “trustee” under the Act.
Sam was one of three lead attorneys in complex trust litigation in Pennsylvania involving the appointment of a successor corporate trustee and the establishment of a private trust company to be that potential successor trustee. Sam was also involved in the multiple appeals resulting from this litigation.
In representing several charitable beneficiaries seeking early termination of a charitable trust, Sam briefed the petition and secured the Illinois Attorney General’s support for trust termination. The court ultimately granted the petition and terminated the trust.
Sam successfully defended her regional bank client against multiple allegations of breach of fiduciary duty.
In acting as risk management counsel to an international financial services company headquartered in Chicago, Sam fended off multiple threats of litigation during the estate and trust administration process, succeeding in completing that process with no lawsuits filed against Sam’s client.
Sam has also obtained numerous favorable decisions reforming or construing wills and trusts.
Admissions
Illinois
U.S. District Court, Northern District of Illinois
Education
Northwestern University School of Law, J.D.
Northwestern University, B.A.
Organizations
Chicago Estate Planning Council
Chicago Bar Association, Probate Practice Committee
Illinois State Bar Association
