Jesse M. Caplan

Managing Director, Corporate Oversight

Boston, MA

Jesse Caplan is Managing Director of Corporate Oversight at Affiliated Monitors, Inc., where he monitors the conditions imposed on organizational clients by government agencies as part of settlement agreements or orders. Mr. Caplan has spent his career focused on ensuring organizational success through enlightened leadership, and the highest standards of corporate integrity, ethics and compliance. In counseling senior leadership and boards of directors, and in leading legal offices in both the public and private sectors, his philosophy and success have been predicated on certain principles: cultivating an environment of respect and openness, insisting on a culture of integrity and compliance, and understanding that most problems can be successfully solved through collaborative thinking and action.

Mr. Caplan has over 30 years of experience as an attorney in both the public and private sectors, much of that time in leadership positions. He has approximately 20 years with government regulatory and enforcement agencies, including as General Counsel of the Massachusetts Executive Office of Health and Human Services (2015-2018), as Chief of the Massachusetts Attorney General’s Office Consumer Protection and Antitrust Division (2000-2008), as the Attorney General of the Republic of Palau (1998-1999) and as a Trial Attorney in the U.S. Department of Justice’s Antitrust Division(1991-1998). Mr. Caplan was a partner with Epstein Becker & Green, while also serving as Chief Legal Counsel for Fallon Health, a Massachusetts not-for-profit HMO (2008-2015).

The majority of Mr. Caplan’s work has been in complex and highly regulated industries. While with the Massachusetts Attorney General’s Office, he oversaw antitrust and consumer protection investigations of the Massachusetts health care, telecommunications, banking and other industries. And most recently as General Counsel for the Massachusetts Executive Office of Health and Human Services, he had ultimate legal responsibility and oversight for the Massachusetts Medicaid program and 12 agencies, including the Department of Public Health, the Department of Mental Health, and the Medical Board.

Mr. Caplan has written and spoken on legal topics, including developments in connection with the Affordable Care Act, antitrust, and federal and state regulatory compliance. He has also served as an Adjunct Professor of Antitrust Law at the Suffolk University School of Law. Mr. Caplan received his JD summa cum laude from the Washington College of Law at American University, and his BA from Colgate University.