Mr. Rupp earned his Associates degree in Movement Learning and Exercise Science from Orange County Community College (Middletown NY), his Bachelor of Science om Movement Studies and Exercise Science with a concentration in Athletic Training and Sports Medicine from East Stroudsburg University (East Stroudsburg PA), and his Masters of Science in Physical Education from Syracuse University (Syracuse NY). 

He has been an athletic trainer at Oakton High School since August of 2000. Prior to working at Oakton HS, he worked for 41/2 years at St. John’s University as an Assistant Athletic Trainer, and 2 years as a Graduate Athletic Trainer at Syracuse University. In his time along with working at Oakton HS, he has served as the VATA Secondary School Committee Chairperson (2001-2008), Virginia High School League(VHSL) Sports Medicine Advisory Committee member (2001-2008 & 2014- present), VHSL Wrestling Rules Committee member (2014-present), VATA Governmental Affairs Committee member (2018-present), and the MAATA representative to the NATA Committee of Professional Ethics (2018-present), and will be the next chair of the NATA COPE. He has been a preceptor for George Mason University, George Washington University, and Shenandoah University. He has worked with Virginia Youth Soccer Association’s Olympic development program, and the Iroquois National lacrosse teams. 

He has presented at the NATA National symposium, the MAATA Annual symposium and the VATA Annual Symposium, and has given presentations at Shenandoah University, and Big Sky Athletic Training and Sports Medicine Conference, and The Academy for Sports Dentistry Conference. In 2011 he was awarded the Vito Parriello Secondary School Athletic Trainer of the Year, and in 2022 he was inducted into the VATA Hall of Fame.