Federal judicial service Dearie was nominated by President Ronald Reagan on February 3, 1986, to the United States District Court for the Eastern District of New York, to a new seat created by 98 Stat. 333. He was confirmed by the United States Senate on March 14, 1986, and received his commission on March 19, 1986.[3] He served as Chief Judge from 2007 until 2011.[6] He took senior status on April 3, 2011, and was succeeded by Judge Pamela K. Chen in March 2013.[7] He remained an active judge on the Eastern District Court; according to a court official, he is planning to go on inactive status at the end of 2022.[8]

On July 2, 2012, Supreme Court Chief Justice John Roberts appointed Dearie to a seven-year term on the United States Foreign Intelligence Surveillance Court.[9][10][11]

Dearie was one of two candidates proposed by Donald Trump and the U.S. Department of Justice as a special master to review documents seized in the FBI search of Mar-a-Lago.[12] The United States Department of Justice announced that it would accept him.[13] He was appointed special master by Judge Aileen Cannon on September 15, 2022.[14]