Cowin graduated from the University of Alabama College of Commerce and Business Administration magna cum laude in 1982 and the University of Alabama School of Law in 1985. Upon graduation, Cowin clerked for Montgomery County Circuit Judge Joseph Phelps, before entering private practice with Ball, Ball, Matthews & Novak in 1986.

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He is admitted to practice in all state and federal courts in Alabama as well as the U.S. Court of Appeals for the Eleventh Circuit. Cowin previously served as president of the Montgomery County Bar Association in 2015. He is also a member of the Alabama Defense Lawyers Association, Defense Research Institute, Alabama Trucking Association, Trucking Insurance Defense Lawyers Association, and Transportation Lawyers Association.

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Cowin is married to the former Holley Crim of Birmingham, and they have two sons. He is an avid University of Alabama football fan and a struggling golfer.