Winston graduated in December 1989 from the University Of Arkansas School of Law in Fayetteville, Arkansas and after passing the bar exam in the State of Oklahoma started his career. He became an Assistant District Attorney for the 13th Judicial District comprising of both Ottawa and Delaware Counties where he served as lead trial attorney until May of 1996.
Since May 1996, Winston has been in private practice with Stockwell & Connor, PLLC. In addition, he previously severed as a member of the Board of Directors of the Oregon Criminal Defense Lawyers Association. As well as a recipient of the coveted Clarence Darrow Award it is given annually to an individual attorney for zealous criminal defense advocacy.
Winston has handled many cases in both State and Federal Courts, as well as cases across the country.