Ben Cassillo is from upstate New York and was a two-time All-Conference selection for Shaker High School, had a career .444 batting average before starting his collegiate career at the University of Virginia.

At UVA, Cassillo was a walk-on player where he was a part of the 2015 National Championship team. Cassillo played alongside 17 teammates who were selected in the top 10 rounds in the MLB draft, including 6 1st round picks. Cassillo graduated from UVA in 3 years, majoring in Economics and minoring in Religious Studies. He currently works as a data analyst for a digital marketing company in the Charlotte area. Ben is entering his 1st year of coaching with the Dirtbags.