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Caitlyn Sikorski is a shareholder in Reinhart’s Trusts and Estates Practice, where she combines her technical knowledge and litigation experience to help clients navigate complex and difficult issues. She adopts her clients’ problems as her own to solve, understanding the highly personal nature of the practice while developing strategies that yield positive results.

Her practice is primarily focused on counseling clients regarding trust, estate and fiduciary litigation, and she is especially skilled in trustee compliance and litigation, including breach of trust, breach of fiduciary duty, undue influence, fiduciary removal and defense, and significant construction and reformation matters. Caitlyn has extensive experience in trust modification and reformation, nonjudicial settlement agreements, prenuptial and marital property agreements, succession planning, guardianships, gift and generation-skipping tax issues and general estate, tax and wealth transfer planning.

Navigating sensitive interfamily dynamics can be challenging, but Caitlyn’s experience and pragmatic approach allow her to find successful resolutions for her clients. She is knowledgeable about the special court proceedings and tax rules that govern trust and estate matters and leverages them strategically. She finds it immensely rewarding to walk with clients through challenging times, providing information and context so they can make informed decisions.

Caitlyn is a Fellow in the American College of Trust and Estate Counsel, an esteemed organization that admits only top-tier members of the profession. She presents annually to the Wisconsin State Bar Association, educating lawyers on fiduciary litigation issues.

Away from the office, Caitlyn spends time with her family and is involved in her children’s many extracurricular activities.


  • J.D., DePaul University College of Law
  • B.B.A., with distinction, University of Wisconsin (Real Estate and Urban Land Economics)

Bar Admissions

Wisconsin | Illinois

Court Admissions

  • U.S. District Court, Western District of Wisconsin


  • Acts as Wisconsin trust counsel for a multinational bank; representation includes advising the Corporate Trustee on all Wisconsin trust and estate related matters, including disclosure of information, approval of accounts, resignation and removal matters, discharge, interpretation and construction questions, identification of tax and procedural issues, and preparation and review of court pleadings and nonjudicial settlement agreements
  • Represented Trustee in marshaling millions of dollars of trust assets fraudulently concealed by the decedent’s spouse
  • Represented Trustee in preventing Trustee removal for breach of trust
  • Represented trust beneficiaries in obtaining and reviewing trust accounts and asset information; assist beneficiaries in marshaling and recovering fraudulently transferred trust assets
  • Assisted Trustee in administering a $20 million estate and trust
  • Traced mixed property totaling more than $8 million to determine asset classification
  • Facilitated dispute resolution in various intra-family conflicts

Honors & Affiliations


  • Best Lawyers in America (Litigation – Trusts and Estates; Nonprofit / Charities Law; Trusts and Estates)
  • Selected for inclusion in Wisconsin Super Lawyers – Rising Stars Edition
  • American College of Trust and Estate Counsel (Fellow)
  • Milwaukee Bar Association (former Chair, Trusts & Estates [Probate] Section)
  • State Bar of Wisconsin (Director - Real Property, Probate and Trust Law Section)
  • Illinois State Bar
  • American Bar Association
After my grandfather passed away, we started to encounter problems with his estate and trust. I chose Caitlyn Sikorski at Reinhart to help my family sort it out. From initial consultation to successful resolution of our issue, Caitlyn was absolutely fantastic to work with and helped get substantial funds returned to my family. She was proactive and empathetic every step of the way, working efficiently to bill reasonable hours and avoid expensive court proceedings when possible. She was very firm with the opposition and helped us advocate for our rights and a fair outcome in a delicate, difficult (and sad) situation for our family. We were so grateful to have Caitlyn on our team. We would not hesitate to work with her again, and we highly recommend her to anyone who needs an attorney.”
Andy Trattner

News & Insights


  • “Annual Fiduciary Litigation Update 2022”
  • “Trust Disputes and Fiduciary Litigation 2018”
  • “Deferred Marital Property,” Guest Lecturer for the University of Wisconsin Law School’s Marital Property Class
  • “Wisconsin Trust Code: So, You Want to Be a Directing Party?”
  • “Nonjudicial Settlement Agreements: How They Work and What Happens When They Don’t”
  • “The Wisconsin Trust Code: New Rules and Guidance”
  • “Guidance for Corporate Trustees under the Wisconsin Trust Code”
  • “Common Mistakes in Estate Planning for Blended Families”
  • “Special Rules for Spouses: Marital Property Issues in Probate and Trust Administrations”
  • “Tax Relief Act of 2010”


  • Death and Dysfunction: Abusing Fiduciary RelationshipsMilwaukee Business Journal (August 27, 2021); Blue Magazine (October 2021)
  • Caitlyn B. Sikorski, Eckhardt’s Workbook for Wisconsin Estate Planners ch. 5 (7th ed. 2019).
  • Sikorski, Caitlyn B. (2016). Detailed Drafting and Nonjudicial Settlement Agreements: Mitigating Litigation Risk and Adding Flexibility. Best Practices for Structuring Trusts and Estates, 2016 ed.: Leading Lawyers on Drafting a Flexible Plan, Protecting the Client’s Assets, and Leveraging Tax Strategies (Inside the Minds). (pp. 7-18). New York, NY: Thomson Reuters.