Alexandra O. Mitchell
Partner
Overview
Alexandra O. Mitchell advises tax-exempt organizations, their donors and the funds in which they invest on complex federal tax matters, helping clients structure transactions, develop philanthropic strategies and resolve IRS controversies. Based in Seattle and Washington, D.C., she draws on two decades of experience counseling operating charities, private foundations, educational institutions and healthcare systems.
Alexandra guides tax-exempt clients through sophisticated transactions, including joint ventures, mergers and alternative investment structures. She regularly represents clients before the IRS in examinations, appeals, private letter ruling requests and applications for exemption, helping them navigate complex tax issues and resolve controversies efficiently.
She also works with high-net-worth individuals and family offices on the design and implementation of tax-efficient philanthropic structures and strategies, aligning charitable goals with broader tax and wealth planning objectives.
Before joining Holland & Knight, Alexandra led the Washington National Tax exempt organizations and philanthropy group at a major accounting firm. Earlier, she was a Washington National Tax managing director and practiced as a tax associate with two international law firms. Her experience in both national tax leadership roles and private practice helps clients address sophisticated tax matters while advancing their organizational and philanthropic objectives.
Representative Experience
- Advised a large tax-exempt health maintenance organization (HMO) on the federal tax implications of its participation in a joint venture with private equity; authored a comprehensive tax opinion, concluding the arrangement would not jeopardize tax-exempt status or generate unrelated business taxable income, and established the governance and operational framework required to maintain compliance
- Advised an organ procurement organization on a comprehensive entity rationalization project; provided strategic counsel on corporate restructuring and tax-exempt compliance to streamline operations and ensure long-term regulatory alignment within a highly specialized healthcare sector
- Advised private foundations on the design and implementation of scholarship programs; applied for and obtained IRS approval of grantmaking procedures
- Advised a single-family office on a comprehensive charitable planning strategy, including the tax-efficient transfer of a significant operating business into a diversified real estate portfolio and strategic oversight of two private foundations designated as estate beneficiaries
- Advised a high-net-worth philanthropist on integrating Section 501(c)(4) social welfare organizations into a comprehensive estate plan; collaborated on a pre-submission conference with the IRS National Office on a first-impression issue at the intersection of exempt organizations and federal estate tax law, providing technical analysis to support the client's long-term philanthropic objectives
- Provided sophisticated succession planning for a high-net-worth family, structuring the transfer of assets into a portfolio of tax-exempt entities, including Section 501(c)(3), 501(c)(4) and 501(c)(7) organizations, to minimize estate tax exposure
- Secured a full concession from IRS Appeals in a high-stakes charitable contribution dispute, successfully defending the deduction under substantial compliance and reasonable cause and eliminating all proposed deficiencies and penalties
- Represented a private foundation in an IRS examination involving complex excise tax issues; limited the scope of the audit through a statute of limitations defense and negotiated a favorable resolution that minimized financial exposure and administrative burden
- Authored a Section 115 tax opinion for a fund of funds comprised of state-owned entities, supporting the tax-efficient restructuring of state assets through a detailed analysis of income exclusion rules
- Advised a closely held real estate fund on a strategic philanthropic structure involving a tax-exempt organization for the development of a senior living community, aligning private investment objectives with charitable development goals
Credentials
- New York University School of Law, LL.M., Taxation
- The George Washington University Law School, J.D.
- Georgetown University, B.A., cum laude
- District of Columbia
- Washington
- American Bar Association (ABA), Section of Taxation, Exempt Organizations Committee, 2006-2026; Real Property, Trust and Estate Section, Charitable Planning and Organizations Group, 2025-2026, Charitable Planning Co-Chair, 2026-Present
- District of Columbia Bar Association, Taxation Community, Exempt Organizations Committee, 2006-2026
- TEGE Exempt Organizations Council, 2019-2026