Mr. McHenry graduated cum laude from the University of Michigan in 1997 with a Bachelors degree in Business Administration. In 2004, he graduated second in his class, magna cum laude, from Lewis and Clark Law School in Portland, Oregon, where his studies concentrated heavily on criminal defense. While in law school, Mr. McHenry was a law review associate editor, and worked as a research clerk for the Federal Public Defender office in Portland, Oregon.

Mr. McHenry first joined the Law Office of Michael Levine (now Levine & McHenry LLC) as an associate attorney in 2004. In 2006, he left private practice to work as a staff attorney in the Portland office of Metropolitan Public Defenders, Inc. While there, Mr. McHenry defended hundreds of individuals charged by the State of Oregon with both misdemeanor and felony crimes.

Mr. McHenry returned to private practice with Mr. Levine in August of 2007, and they formed a partnership, Levine & McHenry LLC, in 2010. Mr. McHenry continues to focus his practice on all aspects of criminal defense.

Mr. McHenry has been a featured speaker at the Annual Conference of the Oregon Criminal Defense Lawyers Association on multiple occasions, and is the author of a chapter in Major Crimes and Defenses, a publication of the Oregon Criminal Defense Lawyers Association. He is a member of the Oregon State Bar and is admitted to practice in the Federal District Court for the District of Oregon as well as the Ninth Circuit Court of Appeals. He is also a member of the Criminal Justice Act Panel, a group of attorneys in private practice that have been selected by the Oregon Federal District Court as qualified to handle federal indigent criminal defense cases. He has been named as an Oregon Super Lawyers Rising Star for the every year since 2012.