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Jonathan Pry has a diverse work experience spanning various roles and industries. Jonathan started their career in 2006 as an Assistant Football Coach at South Carolina State University and held the same position at James Island Charter High School from 2009 to 2012. In 2012, they worked as an Assistant Football Coach at Benedict College.

After that, they worked as a Server at Bonefish Grill for a few months in 2013. In 2014, they joined Saint Thomas More High School as an Assistant Football Coach and later became the Head Wrestling Coach at St. Thomas More Catholic School in the same year.

Jonathan'smost recent role was as a Realtor at Keaty Real Estate, LLC, starting in 2018.

Jonathan Pry attended Stroudsburg High School from 1996 to 1999. After completing their high school education, they enrolled at East Stroudsburg University of Pennsylvania from 2000 to 2003, where they obtained a Bachelor of Science (B.S.) degree in Hotel, Motel, and Restaurant Management. Following their undergraduate studies, Pry pursued further education at Ohio University between 2015 and 2017. During this period, they earned a Master of Science in Athletic Administration degree.