Theodore Doolittle

Judge profile

This profile is summarized from public sources for background context only. It is not an ImmJudge evaluation.

Theodore M. Doolittle was appointed as an immigration judge to begin hearing cases in November 2023. Judge Doolittle earned a Bachelor of Arts in 1986 from Harvard University and a Juris Doctor in 1992 from the University of Connecticut School of Law. From 2017 to 2023, he served as a Healthcare Advocate for the State of Connecticut, heading the Office of the Healthcare Advocate. From 2014 to 2016, he worked for Le Clair Ryan and CGI Federal, concentrating on healthcare anti-fraud matters, in Annapolis and Woodlawn, Maryland. From 2011 to 2014, he served as the first deputy director for Policy and Enforcement at the Center for Program Integrity, Centers for Medicare & Medicaid Services, Department of Health & Human Services, in Washington, D.C. From 2008 to 2011, he was an associate general counsel with United Healthcare’s Legal & Regulatory Affairs Department in Hartford. From 2001 to 2008, he served as an assistant attorney general in the Healthcare Fraud, Whistleblower and Insurance Advocacy Department of the Connecticut Attorney General’s Office. From 1995 to 2001, he was a trial attorney in the Tax Division, Department of Justice, where he litigated in the Appellate Section and the Southern Criminal Enforcement Section in Washington, D.C., including a detail as a special assistant U.S. attorney for the District of Columbia. From 1994 to 1995, he served as law clerk to the Honorable Roger L. Wollman of the U.S. Court of Appeals for the Eighth Circuit in Sioux Falls, South Dakota, and from 1992 to 1994, he served as law clerk to the Honorable James T. Turner of the U.S. Court of Federal Claims in Washington, D.C. Judge Doolittle is a member of the Connecticut Bar.