Coach Siler '01 returned to his alma mater in 2016 and quickly became an integral part of the school community. Before returning, Coach Siler played baseball in Belgium and Portugal, and coached extensively in Europe, serving as a Portuguese National Team Assistant Coach and Academy Development Coach. While in Europe, he coached several club teams to European Cup Qualifiers and International Tournaments in Belgium, France, Czech Republic, Spain, Germany and Italy. He was also a keynote speaker at coaches’ clinics for ISG and MLB International, and was selected to an EBCA program where he interned at UCONN Baseball in 2013. Since returning from Europe, he served as Director of Operations at Extra Innings Baltimore and has worked with the Blue Chips Baseball program. Coach Siler also continues to work extensively with Caliendo Sports International where he works to develop talent and coaches through combining baseball and culture. He has recently traveled to Cuba, Dominican Republic, Japan and Italy helping coaches and players around the globe using the insights he has found as a true student of the game. Coach Siler was named the MIAA A Conference Coach of the Year for the 2025 season, following the Patriots Championship win.