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Professor Calandrillo joined the UW law school faculty in 2000, was named a Charles I. Stone Professor of Law in 2008 and the Jeffrey & Susan Brotman Professor of Law in 2015. Prior to teaching, he clerked for Judge Alfred Goodwin on the Ninth Circuit and practiced corporate law at Foster Pepper in Seattle. Professor Calandrillo graduated magna cum laude from Harvard Law School where he was a John M. Olin Fellow in Law & Economics and a member of the Harvard Journal on Legislation. 

Professor Calandrillo's scholarship utilizes economic analysis to address controversial law and public policy topics, including permanent daylight saving time, minimum wage legislation, property rights, organ donation, compulsory vaccinations, assisted suicide, punitive damages, baseball's designated-hitter and instant replay rules, tort law's eggshell plaintiff rule and U.S. health and safety regulatory policy. His recent articles have appeared in a variety of top law reviews, including Boston University, George Washington, William & Mary, Georgia, Ohio State and Illinois Law Reviews as well as Harvard Journal of Law & Public Policy and Stanford Journal of Law, Business & Finance. 

Professor Calandrillo teaches Contract Law, Law & Economics, Advanced Torts and Law & Medicine, and is a frequent speaker nationally (for UW and Barbri) on those subjects. He has earned the University of Washington's Distinguished Teaching Award and is a five-time recipient of the Philip Trautman Professor of the Year Award at the law school. He served as Associate Dean for Faculty from 2009-10 and was Faculty Advisor to the Washington Law Review from 2007-11. He has co-authored five amicus briefs before the U.S. Supreme Court and served on the Advisory Board of LifeSharers, a national non-profit organization dedicated to saving the lives of patients awaiting organ transplants. 

In his spare time, Calandrillo has built and flown radio-controlled airplanes, and tutored Kim Kardashian on contracts and torts. He was a 3-time winner on Wheel of Fortune and a one-time loser on Dick Clark’s Winning Lines. In 2021, he earned the lowest possible score of 3 on the Glasgow Coma Scale, coming within a couple of minutes of being pronounced dead. Today he tries to help others avoid the same fate.