Rob S. Chaloupka
Senior Associate Probate Attorney | Estate Planning and Administration
Robert S. Chaloupka is an attorney at N.P. Weiss Law focusing on estate planning, estate administration, elder law, and special needs planning. He works with individuals and families to put clear, practical plans in place while guiding fiduciaries and loved ones through the legal and administrative responsibilities that follow a loss. His work also touches on trusts, nonprofit matters, and select business and real estate transactions.
Rob brings more than two decades of experience across private practice, solo practice, legal writing, and education. In addition to advising clients, he has prepared legal materials for attorneys and corporate counsel and taught continuing education seminars on estate planning, trusts, powers of attorney, and special needs planning. That experience informs a steady, thoughtful approach grounded in clear communication and careful preparation.
Before joining N.P. Weiss Law, Rob maintained a solo practice centered on estate planning and administration and previously practiced in a firm setting advising on trusts, contracts, and nonprofit matters. Earlier in his career, he worked as a senior attorney editor, where he focused on developing legal materials and explaining complex issues in a clear and practical way.
Rob earned his Juris Doctor from Case Western Reserve University School of Law and his Bachelor of Arts from Case Western Reserve University, where he graduated summa cum laude and was inducted into Phi Beta Kappa.
Outside of his practice, Rob enjoys biking and spending time with his wife, daughter, and their three cats.
Primary Practice Areas
Rob works with individuals, families, and fiduciaries across several areas related to planning, administration, and long-term decision-making:
Estate Planning
Estate Administration
Elder Law
Special Needs Planning
Real Estate Transactions
Business Transactions
Education
Case Western Reserve University School of Law, Juris Doctor
Case Western Reserve University, B.A. in Political Science and History, summa cum laude
Bar Admissions
Ohio Supreme Court, 2001
Bar Associations
Ohio State Bar Association, Member
Cleveland Metropolitan Bar Association, Member
Presentations
National Business Institute (2017–2021): Prepared written materials for, and delivered, 18 in-person seminars on estate planning, probate, and trust-related topics, including wills, trusts, powers of attorney, advance directives, asset protection strategies, supplemental needs trusts, and estate administration processes.
Ready to Take the Next Step?
If you are considering estate planning, navigating a recent loss, or have questions about your next steps, our team is here to help. Schedule a consultation to discuss your situation and get clear, practical guidance.

