James Montgomery

Washington, DC

I work closely with fiduciaries to ensure that a nonprofit goal is not jeopardized by regulatory restraints.

James Montgomery’s diverse practice encompasses nonprofit and tax-exempt organization operations, the tax aspects of business transactions, compensation and employee benefit matters, and trust and estate administration and planning.

James advises nonprofit and tax-exempt organizations, institutions and private foundations on their various regulated concerns, including the design and structure of charitable, educational, scientific, literary, social welfare, issue advocacy, trade association, social club and fraternal group entities and programs as well as their domestic and international operations. He helps these and other clients obtain the necessary advance and follow-up approvals and rulings from the IRS to secure and maintain their valuable exemption from federal and local taxation. He also helps nonprofits plan for the availability of tax-deductible contributions and tax compliant fundraising activities. James advises governing boards of trustees and other directors concerning applicable regulatory, asset management, operational, fiduciary, compliance and fundraising standards for their organizations, and also helps design and structure  strategic alliances and joint ventures between nonprofits and for-profit entities.

In transactional matters, James concentrates on tax and tax-related aspects of commercial transactions, including partnerships and joint ventures, venture capital, and corporate mergers and acquisitions. He also advises corporate clients on taxation issues involving capital restructuring, asset sales, real estate, patent, trademark and intellectual property, international, insurance, bankruptcy, and general business matters.

James also counsels clients on tax considerations in employee benefits, executive compensation and ERISA. He has extensive experience with tax-qualified and nonqualified retirement (pension, profit-sharing, 401(k), money purchase, IRA and 403(b) tax-sheltered annuity) plans, as well as stock bonus, stock option and other incentive compensation arrangements, and makes sure they comply with all IRS and DOL requirements.

Individuals and families turn to James for advice on estate planning and trust administration, taking advantage of his years of experience with complex and rapidly changing federal, state and local estate and death tax implications. He designs and structures intra-family transfers of business and other closely-held assets through family partnerships and other vehicles, and sets up revocable and irrevocable trust arrangements for the transfer of business, real estate, insurance, personal residences and other assets.

Before joining Foley Hoag, James was associated with another major firm. Following law school graduation he served as Judicial Law Clerk to the Honorable U.W. Clemon, United States District Court for the Northern District of Alabama. Before entering law school James served as an intern in the Office of the Mayor for the City of Atlanta, Honorable Maynard Jackson.


  • Georgetown University Law Center, L.L.M. in Taxation, with highest honors, 1983
  • Georgetown University Law Center, J.D., with honors, 1981
  • Morehouse College, A.B., summa cum laude, Phi Beta Kappa, 1977

Bar and Court Admissions


  • District of Columbia
  • Alabama
  • Georgia


  • U.S. Tax Court


  • Federal Reserve Bank of Boston - Served as special outside counsel advising a governmental instrumentality regarding the design and implementation of a new governmental program designed to stimulate the extension of credit to a broad set of small and medium sized nonprofit organization borrowers.
  • Entegris - Advised a for-profit technology company on the establishment, design, structure and operation of an affiliated charitable private foundation funded with more than $30 million and aimed at pursuing the business’s CSR and charitable goals to promote STEM education.
  • Delta Sigma Theta Sorority - Advised a national membership organization on the design, structure and operation of an affiliated social welfare and issue advocacy organization engaged in legislative lobbying and political campaign activities (including for the 2020 Presidential Election cycle) within permissible IRS parameters.
  • Highland Street Foundation - Served as general legal counsel to a large charitable family foundation with more than $180 million in assets with respect to all matters involving more than $10 million in annual grant making, compliance with the matrix of regulatory restraints on private foundations with respect to self-dealing, taxable expenditures, business holdings, program-related investments, and the special restraints imposed upon private foundations controlled by family members. 
  • Greentown Labs - Advised a public benefit corporation on the establishment, design and operation of a tax-exempt and charitable business accelerator and incubator within permissible IRS standards.
  • Africare - Served as general legal counsel to a U.S. based charitable organization whose exclusive mission is to promote economic development on the African continent; and advised the client with respect to all matters involving charitable fundraising from within and outside the U.S., compliance with domestic and foreign tax and other restrictions on charitable and non-governmental organizations, affiliations and contractual arrangements with non-governmental organizations based in Africa, and regarding the design, development and implementation of charitable programs and activities conducted in Africa.
  • ACCION - Advised a U.S. nonprofit social investment fund in connection with setting up its operations in Latin America and Africa.
  • Mass Design Group - Negotiated the terms of a $40 million grant from a large U.S. based private foundation to our client for the specific purpose of designing and constructing an educational and agricultural institute in Rwanda with the specific goal of transforming both educational and agricultural practices in Sub-Saharan Africa.
  • ISTH - Regularly advised a national organization of scientists spanning more than 60 countries globally regarding OFAC concerns relating to its scholarship programs and travel grants in connection with educational conferences and symposia held outside the U.S.
  • Delta Sigma Theta Sorority - Advised a national fraternal organization in the design and development of a program of gifting from affiliated charitable organizations to fund the conduct of specific educational projects and activities without triggering unrelated business income tax.
  • Emerson College - Advised a Massachusetts educational institution regarding the permissible parameters for publicizing views regarding controversial public policies without violating applicable restrictions on educational institutions barring legislative and political activities. 
  • Industrial Cooperative Association - Advised a client public charity regarding the analysis of its donation, gift and grant revenues in determining its compliance with the “public support test” for purposes of avoiding private foundation status.
  • Massachusetts Charter Public Schools Association - Advised an association of charter public schools regarding the parameters for permissible lobbying activities both directly and through nonprofit affiliate organizations and institutions.
  • Phillips Academy - Advised the Finance Committee of a Massachusetts secondary school regarding mandatory and permissible changes to its Endowment Spending Policy by reason of the enactment of the Uniform Prudent Management of Institutional Funds Act.
  • TB12 Foundation - Advised a client public charity regarding the design of a nationwide fundraising campaign for donations and gifts, and the potential engagement of professional fundraisers to implement the campaign in accordance with state and local jurisdictional requirements. 


  • Empowerment Zone Wage Tax Credit: A Handbook (1996) - Published by the National Congress for Community Economic Development; funded by The Annie E. Casey Foundation
  • Retirement and Pension Plans / Cost of Living Adjustments for Nonprofit Organizations, Foley Hoag Alert, November 2016
  • Approaching Deadlines for Offshore Account / Investment Reporting, Foley Hoag Alert, April 2015
  • Limits on IRA-to-IRA Rollovers, Foley Hoag Alert, November 2014
  • New Changes in Calculating DC Estate Tax Liability Alert, Foley Hoag Alert, October 2014
  • Tax Whistleblowing Made More Attractive, Foley Hoag Alert, September 2014
  • Estate Tax Return Filing Requirement for Portability, Foley Hoag Alert, August 2014
  • New Law Governing Trusts in Maryland, Foley Hoag Alert, July 2014
  • New Changes in Calculating DC Estate Tax Liability Alert, Foley Hoag Alert, May 2014
  • 2015 Estate and Gift Tax Exclusions, Foley Hoag Alert, January 2014
  • Expansion of Health Insurance Premium Tax Credit, Foley Hoag Alert, September 2013
  • New Medicare Taxes, Foley Hoag Alert, July 2013
  • Fresh Start Resolution of Employee v. Independent Contractor Issues, Foley Hoag Alert, June 2012

Honors & Involvement

  • ABA American Law Institute, Lecturer, 1995
  • National Bar Association, Tax Section Secretary and Lecturer
  • Advisory Group to the Commissioner of the Internal Revenue Service, 1994-1996
  • White House Conference on Small Business, Minority Delegation Expert on Taxation, 1995
  • Mayor’s Select Task Force on Business and Corporate Taxation in the District of Columbia, 1993-1994
  • Conference on Minority Partners in Majority Corporate Law Firms
  • President’s Advisory Commission on Policy Affecting Poor and Disadvantaged Youth, 1978-1979