Barbara Grayson is a partner and Midwest Chair of Willkie’s Private Wealth Group. She represents high-net-worth individuals and families, family owned businesses, family offices and charitable organizations on a wide range of legal issues related to family owned businesses, private equity investments, proprietary funds, family offices, private trust companies, charitable organizations, multigenerational wealth, governance and succession issues, and fiduciary responsibilities. She has extensive estate planning experience, including structuring solutions for transferring wealth to younger generations and succession planning for complex family situations.

Chambers High Net Worth consistently recognizes Barbara in the Band 1 category among the leading Private Wealth practitioners in Illinois and among the Central Region in the United States. The 2023 edition cites that Barbara "is at the top of her profession with an uncommon intellect yet an ability to translate it into accessible and innovative solutions for clients," and one client notes that she “is excellent at efficiently synthesizing complexity and pragmatism. She will be my estate lawyer until death do us part.” A past edition reported that Barbara "has the ability to decode the labyrinth of legal elements of tax and estate planning such that I can understand them and make informed decision."

Barbara regularly counsels clients through a variety of major life events, such as establishing a family foundation, developing a business succession plan, negotiating premarital agreements, administering the estate of a deceased family member and establishing gift trusts for children or grandchildren.

Barbara’s tax planning experience is focused on gift, estate and generation-skipping transfer taxes. She works with clients to design and implement estate plans, including wills, trusts and lifetime gifts. She also structures partnerships, limited liability companies, corporations, shareholder agreements and buy-sell agreements. She counsels clients regarding sophisticated planning for family businesses, including corporate recapitalizations, corporate governance, intrafamily sales and family partnerships. She also has experience in the international aspects of the estate planning practice.

A sizeable portion of Barbara’s practice focuses on philanthropic matters, including the representation and advising of tax-exempt organizations and the representation of individuals with respect to charitable giving. She has helped clients to establish public charities, private foundations and private operating foundations, and she also counsels clients as to best practices in administering those organizations in light of the complicated tax rules surrounding their governance and permissible activities.

Barbara’s practice also includes probate and trust administration, as well as litigation counseling on contested tax, trust and estate matters. She often represents fiduciaries and individual beneficiaries in the administration of estates and trusts. Barbara has experience in a variety of tax, trust and estate disputes, including controversies over will and trust construction, the impact of premarital agreements and divorce decrees on estate administration, and alleged breaches of fiduciary responsibilities.

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Prior to joining Willkie, Barbara was a partner at another major law firm.

  • Euromoney Women in Business Law – Shortlist, Wealth Management Lawyer of the Year, 2024
  • Chambers HNW
    Private Wealth Law - Illinois, 2018-2023
    Private Wealth Law: Central Region – USA, 2022-2023
  • Corporate Counsel 
    “Thought Leadership Award” Women, Influence & Power in Law, 2023
  • American College of Trust and Estates Counsel (ACTEC)


  • Crain’s Chicago Business' 
    Notable Women in Law, 2024, 2022
    Notable Gen X Leaders In Accounting, Consulting And Law, 2021
  • Best Lawyers in America
    Trusts and Estates, 2017-2024
    Closely Held Companies and Family Businesses Law, 2023
  • National Law Journal
    "Trailblazer - Divorce, Trusts & Estates," 2017
  • Leading Lawyers Network
    Closely and Privately Held Business Law, 2016-2019
    Trust, Will and Estate Planning Law, 2016-2019

Barbara is a fellow of the American College of Trusts and Estates Counsel (ACTEC) and a member of the Chicago Estate Planning Council. She is a member of the Economic Club of Chicago and serves on the Board of Trustees for the Chicago Zoological Society, the Goodman Theater Spotlight Advisory Council, the Lyric Opera of Chicago Planned Giving Advisory Council, the Chicago Community Trust Professional Advisory Committee, and the Women in Law Empowerment Forum National Advisory Board. Barbara is also a member of the Fiduciary Professions Committee of the editorial board of Wealth Management's "Trust & Estates" magazine.

  • Co-Author, “General Trust Administration Issues For Fiduciaries,” Trusts & Estates, May 2024
  • Co-Author, “Drafting Trusts to Stand the Test of Time,” Trusts & Estates, November 2019
  • Co-Author, “Avoid Private Trust Company Pitfalls,” Trusts & Estates, November 2018
  • "Minimize Litigation Risks in Estate Plans,” Trusts & Estates, May 2016
  • "What Mom and Dad Really Wanted: Interpreting the Settlor's Intent Within the Trust," Forty-First Notre Dame Tax & Estate Planning Institute, September 17, 2015



Harvard Law School, J.D. University of Missouri – Kansas City, B.A.

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