John W. Leonard

John W. Leonard is an Associate Attorney at Dawson | Orr with experience helping clients through challenging and difficult legal matters that arise in everyday life, whether professionally or personally. His primary practice areas include Commercial and Business Litigation, Construction Litigation, Real Property Litigation, and Personal Injury Litigation.

Originally from Baltimore, Maryland, John received his undergraduate degree in political science from the University of Richmond before beginning the first chapter of his professional career in Washington, DC. That chapter included work at the U.S. Chamber of Commerce, where John first recognized the value of a legal education as a means to promote the interests of others on Capitol Hill, before Federal agencies, and in court. Ultimately, John returned to school to secure his own legal education and pursue the second chapter of his professional career as a licensed attorney. He graduated, with honors, from The Catholic University of America, Columbus School of Law, in Washington, DC, in 2010, and was admitted to the Maryland Bar the same year.

While in law school, John clerked for an administrative judge for the Equal Employment Opportunity Commission and was Editor-in-Chief for The Journal of Contemporary Health Law and Policy. His article analyzing the potential impact and unintended consequences of Congress’ ADA Amendments Act was published in 2010. Later that year, John began his career in litigation with a private Maryland firm where he successfully represented individuals, small businesses, and large corporate clients through numerous contract and personal injury disputes.

John was admitted to the District of Columbia Bar in 2012. The same year, he joined the DC-based litigation team at a nationally recognized law firm, where he assisted in defending clients that often faced potential exposure for personal injuries beyond primary liability limits, typically above one million dollars. The work took John across the country and included cases in Washington, Oregon, California, Arizona, Colorado, Missouri, Georgia, North Carolina, and New Jersey.

In September 2015, his wife Elizabeth, a Jacksonville native and fellow Columbus School of Law graduate, lured John to the Sunshine State. He passed the Florida Bar exam and was admitted to practice in May 2016. In 2017, the couple welcomed their son, Henry, to a family that already included a large Labrador and Goldendoodle. In his free time, John enjoys golfing and teaching his son all about the Baltimore Ravens and Orioles.

Whether it is continuing to promote the interests of the local business community through the Jacksonville Chamber of Commerce, or representing clients in litigation throughout Florida, John is committed to helping his clients by drawing upon every chapter of his professional experience.


  • Maryland, 2010
  • District of Columbia, 2012
  • Florida, 2016


The Catholic University of America, Columbus School of Law; Washington, DC

  • Juris Doctor, cum laude, 2010
  • Editor-in-Chief, The Journal of Contemporary Health Law and Policy

University of Richmond; Richmond, VA

  • Bachelor of Arts, 2002
  • Political Science (major) and History (minor)
  • Music and Performing Arts Scholarship Recipient


  • Jacksonville Bar Association
  • Jacksonville Association of Defense Council
  • Jacksonville Women Lawyers Association
  • Jacksonville Chamber of Commerce

Based in Jacksonville, Florida the attorneys at Orr | Cook draw upon over 100 years of combined legal experience to serve clients throughout Florida and across the country.