Leonard grew up in the Seattle area and graduated from Mercer Island High School. He attended the University of Washington, where he graduated summa cum laude in Psychology. After college, he attended Harvard Law School, where he was twice awarded the Sears Prize (given to the top two students on the basis of grades) and graduated magna cum laude in 1991. He then worked as a judicial law clerk for Ninth Circuit Judge Jerome Farris.

Since completing his Ninth Circuit clerkship, Leonard has specialized in appellate practice before the Ninth Circuit and the Washington appellate courts. In addition to briefing and arguing countless appeals, Leonard is a member of and was previously Chair of the King County Bar Association’s Appellate Section, is a member of the Washington Appellate Lawyers Association, and is currently a District Coordinator for the Ninth Circuit Pro Bono Program and a member of the Ninth Circuit’s mentor program. He is also a frequent writer and speaker on topics relating to appellate practice. Among other articles, he has co-authored three articles with Washington Court of Appeals Judge Stephen Dwyer regarding appellate brief writing, oral argument, and discretionary review.

Leonard has received many accolades for his work, including being listed in Best Lawyers in America (Appellate Practice); selected as “Local Litigation Star,” Benchmark Litigation (Commercial Litigation); and selected as one of Washington’s Top 10 Appellate Law Lawyers by Washington Law and Politics. Leonard has also received two Certificates of Appreciation from the Ninth Circuit, one for his work as a Pro Bono Coordinator and the other for teaching an appellate practice course at the University of Washington School of Law that provided students with an opportunity to brief and argue a pro bono appeal in the Ninth Circuit. In 2006, he received the Washington Bar Association’s Pro Bono Award for his work in appeals that raise important civil rights issues.

Leonard is admitted to practice before the U.S. Supreme Court, the U.S. Court of Appeals for the Fifth, Eighth, Ninth, and Tenth Circuits, and Washington appellate courts.  He was counsel of record and argued in the United States Supreme Court in City and County of San Francisco v. Sheehan, Case No. 13-1412 (2015), and County of Los Angeles v. Mendez, Case No. 16-369 (2017).  His briefing and argument in those cases can be found here and here, respectively.

Leonard is also a devoted husband and father of two children—Ben and Tyler. In his free time, he runs, bikes, and swims and follows the local jazz scene where his sons can be heard playing upright bass (Ben) and guitar (Tyler).