John J. Cleary

John J. Cleary

Of Counsel
John J. Cleary
+1 617 570 1199

Jack Cleary, of counsel in Goodwin's Financial Industry practice, specializes in all aspects of ERISA and employee benefits and has over 35 years’ experience representing clients in connection with such matters. He has particular experience advising clients, primarily financial services institutions, on Title I of ERISA, including fiduciary, investment and prohibited transaction matters. In addition, Mr. Cleary counsels on establishing and operating collective investment fund vehicles for institutional investors, including VCOCs and REOCs, as well as developing a variety of new investment practices and products. He also teams with the firm’s ERISA litigators in defending such clients against ERISA claims.

Mr. Cleary has served as chair of the firm’s Partnership Committee and on its Executive, Management and Allocations Committees.

Since 2009, Mr. Cleary has been recognized at the top of his field in Chambers USA, where clients say he has “always been considered a superstar" in the employee benefits and compensation space.


Mr. Cleary has extensive experience dealing with the Department of Labor on ERISA matters, including prohibited transaction exemptions and advisory opinions, as well as DOL audits and enforcement actions, and he frequently represents trustees, investment managers and other fiduciaries concerning their fiduciary responsibilities under ERISA. His representative matters include:

  • On behalf of an investment adviser client, obtained one of the two seminal DOL advisory opinions authorizing the payment of incentive compensation under ERISA
  • Teamed with ERISA litigators in obtaining a dismissal of all ERISA claims alleging fiduciary breach and unreasonable compensation against John Hancock Life Insurance Company in a case pending on appeal in the Third Circuit
  • As a part of his substantial practice in the stable value area, assisted two money center banks in successfully winding down their stable value collective investment funds
  • As special ERISA counsel, currently seeking to obtain a DOL prohibited transaction exemption that would enable, both retroactively and prospectively, a plan sponsor client to contribute notes issued by an affiliated entity to its defined benefit pension plan in satisfaction of its funding obligation to the plan
  • Obtained the first DOL advisory opinion holding that Section 408(b)(8) of ERISA provides exemptive relief for self-dealing prohibited transactions under Section 406(b)(1)
  • Assisted a major financial institution in restructuring, renegotiating and redocumenting its entire stable value book of business after the financial crisis

Professional Activities

Mr. Cleary is a member of the Employee Benefits Committee of the Tax Section of the American Bar Association, a past co-chair of the Employee Benefits Committee of the Boston Bar Association and a former director of the New England Employee Benefits Council and of Catholic Memorial School.




Harvard Law School

(magna cum laude)

Master of Philosophy1970

Yale University


Massachusetts Institute of Technology



  • Massachusetts


  • U.S. Court of Appeals for the First Circuit
  • U.S. District Court for the District of Massachusetts

Recognition & Awards

Mr. Cleary has been recognized by The Best Lawyers in America Best Lawyers for his work in Employee Benefits (ERISA) Law and Litigation - ERISA 2022-2023.

Mr. Cleary has been selected for inclusion in Chambers USA: America’s Leading Lawyers for Business, U.S. News-Best Lawyers and The Legal 500 U.S.