A sixth-generation Texan, Ray Wheless earned his juris doctorate degree at the University of Texas at Austin, following his completion of a Bachelor of Business Administration at California State University.  Prior to earning his educational degrees, he served his country in the United States Air Force.  He is Board Certified in Personal Injury Trial Law (1989), Civil Trial Law (1990), and Criminal Law (2016).

Ray began his career as an attorney in 1980 with the Law Offices of Raymond G. Wheless, continuing to practice law in the areas of civil trial and criminal law over the next 20 years.  In 2000, Ray made the shift into a judiciary role as a County Court Judge in Collin County, maintaining that role until 2009, when he was appointed to the position of 366th District Court Judge by Governor Rick Perry.  Governor Greg Abbott appointed him to the position of Regional Presiding Judge of the First Administrative Judicial Region of Texas in 2018.

Among his many accomplishments and roles that he has been honored with, Ray has served as the Chairman of the Specialized Courts Advisory Council, President of the Texas Association of Specialty Courts, President of the Collin County Bar Association, President of the Plano Bar Association, and President of the Plano Metro Rotary Club.