Joshua R. Caswell

Joshua Caswell works with clients of Choate’s Wealth Management Group. With a focus on representing principals of private equity, venture capital and hedge funds, as well as corporate executives, business owners and entrepreneurs, Joshua counsels successful individuals and families in all matters related to preserving, enhancing and transferring family wealth. 

Joshua provides clients with sophisticated estate planning and estate settlement strategies that take advantage of tax minimization opportunities in a manner that is consistent with their values and objectives.  Additionally, he has represented many clients in the acquisition, management, preservation and perpetuation of “heirloom” properties.


  • Super Lawyers Rising Star
  • Probate & Property Magazine's 2021 Excellence in Writing Awards - "Best Cutting-Edge Article"

Publications and Presentations

  • “Planning for and with Heirloom Properties & Vacation Homes,” presenter, Boston Estate Planning Council, May 2022.
  • "Business Succession and Estate Planning with ESOPs,“ speaker, National CLE Conference for the ABA's Real Property, Trusts and Estates Section, April 2022.
  • “Til Death Do Us Part, Again: How Divorce, Remarriage and Other Shifting Family Paradigms are Impacting Planning for the Modern Family (Parts I and II),” presenter, Estate Planning Council of Rhode Island, December 2021.
  • “Nfts for estate planners: not just a token concern,” co-author, Probate & Property Magazine, September 2021.
  • “Accounting and Tax Crash Course for Trusts and Estates,” presenter, National Business Institute, June 2020.
  • “Massachusetts Limits Opportunity Zone Benefits,” author,, July 2019.
  • “Opportunity Zones: Maximizing Impact – Issues and Perspectives on How To Structure a Deal,” presenter, American Bar Association’s 31st Annual National CLE Conference, May 2019.
  • “Trust Us: Key Drafting Considerations and Ideas for Modern Wills and Trusts,” presenter, Rhode Island Bar Association, May 2019.
  • “Trust Planning Playbook: Understanding and Using Trusts in Estate Planning,” presenter, Rhode Island Bar Association, May 2018.

Professional and Community Involvement

  • Fellow of American Bar Association, Real Property, Trust and Estate Law Section
  • Co-Chair of New Developments Committee of the Trusts & Estates Section of the Boston Bar Association
  • Member of American Bar Association, Section of Real Property, Trust and Estate Law
  • Member of Rhode Island Bar Association Committee on Probate and Trusts

Education & Credentials

Suffolk University Law School
JD, 2012, cum laude
University of Massachusetts Amherst
BS, 2009, cum laude