Complex sentence: He broke into Colchester's under-18 side while still an under-16 player, and was the first Colchester Academy player to come through the educational system associated with Thurstable School in Tiptree.
Split into simpler sentences: He broke into Colchester's under-18 side while still an under-16 player. He was the first Colchester Academy player to come through the educational system associated with Thurstable School in Tiptree.