He was a law clerk to Buell A. Nesbett, chief justice of the Alaska Supreme Court, from 1961 to 1963.

Holland was confirmed by the United States Senate on March 26, 1984, and received his commission on July 16, 1984.

[2] Holland serves as a visiting judge in the District of Arizona,[3] having first presided over a case in that court in 1993.

[5] Notable trials he handled were 2014's United States v. Town of Colorado City, Ariz., et al., in which the local government was controlled by leaders from FLDS sect of Mormonism,[6][7] and consolidated Theranos litigation (Toy v. Theranos, Inc., et al.)[8] from October 2016 until June 2020 when he requested it be reassigned.

He was formerly (until June 2020)[9] the presiding judge in a class action lawsuit against Theranos founder Elizabeth Holmes.