Jonathan Taylor graduated from Crystal Springs Uplands school in Hillsborough, California. He swam with Palo Alto Stanford Aquatics for 4 years before moving on to college swimming. His start in competitive swimming began at the age of 9 as a summer league swimmer. Jonathan began year round swimming in 2002. Since 2002 he has qualified for Junior Championships in the 50m freestyle and in 2005 and 2006 he made finals in the 50m freestyle at the California-Nevada Sectionals. On his high school team, Jonathan set records in the 100y freestyle, 100y butterfly, 200y freestyle and 200y IM. He was a finalist at his high school championship his sophomore through senior years. In his first year at Yale Jonathan was a member of the ECAC Championship squad swimming the freestyle and butterfly events and the relays.

As a student Jonathan participated in many different extra curricular activities at Crystal Springs Uplands School. He was president of the student body his senior year and a class representative his junior year. He was involved with the C.A.F.E. club, an organization designed to promote diversity.