Complex sentence: He attended Philips Exeter Academy and Harvard College before entering the United States Naval Academy in 1905 from which he graduated in 1909 and was assigned to the USS "Villalobos" (PG-42) on October 29 of that year.
Split into simpler sentences: He attended Philips Exeter Academy and Harvard College before entering the United States Naval Academy in 1905. He graduated from Annapolis in 1909 and was assigned to the USS "Villalobos" (PG-42) on October 29 of that year.