Jesse was born and raised in Olympia, WA. He graduated from Capital High School in 2003 where he was a three-year letter-winner in baseball. At Capital, Jesse was named 1st Team All League his junior and senior years, as well as being named All-State his senior year. Jesse went on to become the starting shortstop for four years at the University of Portland (’04-’07). At the end of his career, he held the assists record for the Pilots with 528, was 2nd in career games played with 204, was the Team Captain his senior year, and was the All West Coast Conference Honorable Mention Shortstop in 2005. In the summer of 2004, Jesse played for the NBC World Series Champion Aloha Knights (now the Corvallis Knights). In 2006, he played in the NBC World Series for the Palm Springs Power, assisted by former Oxy Head Coach Jason Hawkins. After finishing his playing career, Jesse jumped right into coaching, becoming the Volunteer Assistant for the University of Portland in 2008. He coached infielders and hitters as well as throwing batting practice every day.