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James Roosevelt, Jr.

James Roosevelt, Jr.



  • Health Care
  • Health Care & Life Sciences
  • Strategic Counseling & Transactions
  • Government Enforcement & Compliance

WSG Practice Industries


Massachusetts, U.S.A.


Jim advises health care payers, providers, trade associations, and service providers on business matters, legislative and regulatory issues, governance, and personnel matters. He regularly represents medical device and medical process startups, including with respect to telehealth, artificial intelligence, and treatment utilizing legal psychedelics. He is also a national speaker and author on the Affordable Care Act, Medicare and Medicaid policy, and Social Security.

For more than 10 years, Jim was CEO of Tufts Health Plan, where he led a turnaround that nearly doubled the membership and achieved consistent profitability while attaining #1 ranking in the United States from the national accrediting organization. He was previously in-house General Counsel and was a former partner in the Health Care Practice Group of Choate, Hall and Stewart in Boston. Before joining Tufts Health Plan, he served as Associate Commissioner of the U.S. Social Security Administration.

In 2016, Jim was a visiting fellow at the Institute of Politics of the Harvard Kennedy School of Government. He continues as a clinical instructor in the Public Health and Community Medicine Department of Tufts University School of Medicine.

Public policy and politics are Jim's personal passions. He co-chairs the Rules and Bylaws Committee of the Democratic National Committee and is volunteer legal counsel for the Massachusetts Democratic Party. He is a trustee of the Cambridge Public Library and the Cambridge Community Foundation. He has co-chaired Rhode Island Governor Gina Raimondo's Healthcare Leaders Task Force on Health Care Cost Growth, and he co-chaired the Massachusetts Hospital Association's work group on access to behavioral health care.

Jim and his wife, Ann, enjoy living near their daughters and their husbands and three grandsons in Cambridge, MA, as well as visiting their daughter, her husband and their newest grandson in Washington, DC.

Bar Admissions

  • Massachusetts
  • Washington, D.C.


  • Harvard Law School (J.D.)
  • Harvard College (B.A.)
  • Harvard Business School (Advanced Management Program)
Areas of Practice

Government Enforcement & Compliance | Health Care | Health Care & Life Sciences | Strategic Counseling & Transactions

Professional Career

Professional Associations

  • American Health Lawyers Association
  • Boston Bar Association, Health Law Committee
  • American Bar Association, Health Law Section
  • Massachusetts Hospital Association, Life Member

Professional Activities and Experience

  • AV Preeminent Rated by Martindale-Hubbell
  • Emmanuel College, Boston, Massachusetts, Commencement Speaker and Honorary Degree (Dr. of Laws, 2011)
  • William James College, Newton, Massachusetts, Honorary Degree (Dr. of Humane Letters, 2017)
  • Listed in The Best Lawyers in America© under Health Care Law

To learn more about third-party ratings and rankings, and the selection processes used for inclusion, click here.

WSG's members are independent firms and are not affiliated in the joint practice of professional services. Each member exercises its own individual judgments on all client matters.

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